Style

How I Found My Personal Style

Ashley Ford

In the summer of 1998, when I was a child desperate to be a teen…

I read this in a magazine: “Clothes are easy, but style is hard.” The person I went shopping with as a kid was my grandmother. It was our favorite activity, strolling through malls and department stores any given Saturday. Combing the sale racks with eager hands and sharp eyes. My mother didn’t have much disposable income, so one of the ways my grandmother helped her was by buying most of my clothes. Nobody had a closet like my grandmother’s. It overflowed with pantsuits, cardigans and furs. Almost every dress had a matching handbag and/or pair of shoes, and there was no shying away from animal print. My grandmother’s style was all her own, and if it was hard, she made it look easy.

She always hoped I would mimic her more, but I didn’t. Even then, I knew her look wasn’t my look. When I told her, she responded, “So, what is your look then?” Devoid of a clear answer, I said, “I’ll figure it out.” When I asked my grandmother how she’d found hers, she said, “I didn’t find a style really. I just wear what I like.” I thought must be nice, and changed the subject.

In high school, I wanted clothes from particular stores, no matter how well the clothing actually fit me. And unfortunately, no matter how much I wanted to look like a teenager on TV, my Midwestern hips actively revolted against the seams of their low-rise jeans. My junior year of college, I gave up on pants completely. My entire wardrobe became a series of dresses picked up on sale at Target, J.C. Penny or The Gap Outlet. I didn’t know how to dress a larger body. Besides, there didn’t seem to be many things to choose from in bigger sizes. I languished in oversized sweaters and sweatshirts, didn’t wear makeup, and just waited to be cute (and thin) again. I’d weighed around 200 pounds for several months before I began to feel heavy. I withdrew from my life. I saw friends less and less often. Who wants to go out when you know you won’t feel good when you get to wherever it is you’re going?

It’s strange how much clarity we can gain from a person’s words after they’re gone. When my grandmother died in January of 2015, I was heartbroken. I flew back to Indiana, drove to her house, and plucked a simple black sweater from her closet to wear to the funeral. I wanted to smell like her when I said goodbye. I also went into her bathroom and found a brighter shade of lipstick, the kind she always asked me to wear. Despite the sadness of the day, my mother, aunts and cousins all mentioned that I looked fantastic. I smiled and thanked them through tears. The odd thing was, I believed them. In that moment, I liked the way I looked more than I ever had before. In a striped grey dress, a black cardigan, and the brightest lipstick my mouth had ever worn, and on the saddest day of my life, I felt beautiful. I was devastated, but so very happy to be alive.

When I came back to New York, after the funeral, I kept thinking of my grandmother’s words — I just wear what I like — and suddenly, nothing had ever made more sense. I cleaned out my closet. There were many things I wore all the time, but didn’t actually like. I didn’t have much money to buy new clothes, so I went back to what I knew, combing sales racks with a sharp eye. I walked into stores with an open mind, tried on things in a variety of sizes, but still often left empty-handed. So, I tried something new. I finally went shopping online.

For years, I’d avoided events that would require me to dress up. To be honest, the phrases ‘Cocktail Attire’ or ‘Black Tie’ still make me quake in my boots. (I literally spent years thinking, ‘I hope nothing fancy happens.’) But Eloquii and Torrid offered me gold gowns that shimmered in the streetlights, floral sundresses, and all the fun celebratory clothing I couldn’t find in my size at most stores. ModCloth and ASOS Curve gave me fun quirky pieces that spoke to the more whimsical parts of my personality, like royal blue cropped sweaters and dresses bearing the faces of my favorite comic book characters. Universal Standard took all the simple and sleek designs I thought didn’t work for a body like mine, like shirt dresses, and showed me I still had so much to learn about what a quality well-built garment could really do for a bigger body.

Slowly, but surely, I built a wardrobe that for better or worse felt like me. I waited for sales, or saved my money and invested in pieces I stalked for months. I modeled my new clothes for my fiancé, and watched his face light up not just because I looked good, but because I looked happy. When I glanced in the mirror, my face brightened as well. Happy looked great on me.

Now I make sure I like everything in my closet. If not, it goes back on the rack, gets returned, or is promptly donated. When I find clothes that fit well, I feel more comfortable and confident and, it turns out, I feel better about the body I already have. I go out more, I smile more, and when someone looks at me now, I know they’re seeing the version of me I chose. Not the only version I had access to.

My grandmother gave me so much while she was alive, and most of it had nothing to do with clothes. Still, whenever I put on a bright lipstick, or a black cardigan, I think of her and how much she loved me. It reminds me to love myself, just as I am, and to dress as if that’s the case. I spent years of my life believing my best looks were behind me, but now I’m in the midst of a body revolution. My personal style will grow as I do. That magazine in 1998 lied. Clothes aren’t always easy. But style doesn’t always have to be hard.

Ashley Ford

P.S. Ashley’s week of outfits, and body confidence in a relationship.

(Photos courtesy of Ashley Ford.)

  1. Nikki says...

    Thank for this beautiful piece. Struggling so much at the moment to like or love myself, physically, intellectually and emotionally I feel like I am failing in who and how I should be. This is a reminder that loving yourself is really not easy, but its also not so hard. Maybe I should start with putting on my favourite outfit, which feels like myself.

  2. I love this. Good to see your work here.

  3. karen says...

    Beautiful and inspiring! Thank you so much!

  4. Caitie says...

    Such a sweet story about a lesson learned and a tribute to a loved one’s wise words. I am a married mama and I know that I’m lucky to be slim abandoned athletic, but even so I totally relate to this story as I feel little time to see dedicate to myself let alone my look! I wear what I have that was probably bought on sale at the Banana Republic factory store and don’t really feel like myself when I lop in the mirror. But this story has reminded me that life is short and with a little effort, maybe I could feel better about my look if I made a little time for myself.

  5. Ursa says...

    Ashley, what a great article. I am happy with you. I think this is such a positive attitude.

  6. Lizzy says...

    What a lovely story. Thank you Ashley….,I love your writing and hope to see more of it. Your grandmother sounds like an amazing woman.

  7. Caroline says...

    Such a lovely story! Thank you so much for sharing.

  8. Stacey says...

    As a, grandmother raising my grand daughter, this piece touched me deeply. Devastation and aliveness, self live, shared wisdom. Wow.

  9. Maria says...

    I love it, through the specifics of your story you are re telling mine and I think (mostly maybe) everyone else’s. Thank you so much.

  10. Anita Jensen says...

    Thank you, very moving.

  11. Es says...

    Love the bond between you and your grandmother.

  12. Maddy Corey says...

    Best article I’ve read all day!

  13. Wei says...

    “Now I make sure I like everything in my closet.”
    Thank you, sometimes you just need to hear it from another person to remind yourself of what should be common sense.

  14. Katherine says...

    Lovely, I’m so glad there will be more from Ashley! I admire her; she shares herself so beautifully with the world.

  15. Melanie says...

    I love this post so much. Heartfelt and honest and a beautiful way to honor your grandmother as well.

  16. Molly B. says...

    Love your confidence and authenticity, such beauty. I feel so inspired and grounded by this piece – Ashley, you are amazing!!!

  17. Love this.

  18. Erin Butler says...

    Bravo!!!! This brought me to tears and made me miss my Grandma so much…and her coral lipstick

  19. Meredith Whitfield says...

    ASHLEY

  20. Xo says...

    Love this! And especially the reader comment that it speaks to her about coming to terms with how you look as you age. Not as evolved as Ashley yet but this is a good kick (nudge?) to think differently nicely timed for holiday parties and family reunions!!!

  21. Sasha says...

    That photo of you and your grandma, so much love just beaming out from both your faces. Thank you for this inspiring and hopeful piece. Hooray for finding ourselves, being ourselves, loving ourselves.

  22. Aliez says...

    YES. THIS! Thank you Ashley for your words and your voice. The line that gave me chills was “It’s strange how much clarity we can gain from a person’s words after they’re gone.” To me, it resonates not only with ones style, but with one’s memories, their photos, and their dreams. I work with seniors and families with seniors, and it’s such a poignant thing to see that clarity pass through a living loved one. People really are with us after they’re physically gone. I am so thrilled that you’ve joined the Cup of Jo team. More please!

  23. LR says...

    What a great piece.

  24. Caitlin says...

    This reminds me of my relationship with my grandma- who also loved a bright lipstick. I still have one of her cardigans and it’s my most prized possession.

  25. Wendy says...

    Thank you for sharing about your wonderful grandmother. ❤️

  26. Nadine Hughey says...

    I was excited to see you’d become a part of the team after your Week Of Outfits. Clothes can be a real bugaboo no matter what the size, but it’s so much better when we can enjoy them.

  27. I’m not a size zero nor will I ever be, I have boobs and carry weight on my stomach. I envy the girls who have a flat stomach but I know that will never be me as its just not the way my body is made which is fine.
    I wear clothes that make me feel confident and while I do tend to stick to classic styles that’s just what looks best on me.
    I really relate to this article Ashley as that’s what I do too, I wear what I like and my wardrobe reflects that. I’m not afraid to splurge on pieces like a fun dress or black trench (which I practically live in in Winter) if I know I will wear them. Shopping for clothes shouldn’t be a chore, it should be fun and we shouldn’t be afraid to take risks when it comes to clothes.
    I would love Ashley to do a piece on her most worn items in her wardrobe along with a few random things she has and why she won’t part with them.

  28. Dina says...

    Holy smokes, Ashley, we have been waiting for you for a very long time. Thank you for coming and sharing your grandmother’s wisdom, as well as your own. Your pen is a magic wand with which you empower women with words we’ve needed to hear. Thank you.

  29. Jenny Leigh says...

    Oh Ashley, this is just beautiful. My grandmother has always been my style and beauty inspiration as well. I can’t wait to read more of your pieces on Cup of Jo!

  30. Daynna Shannon says...

    I am so, so happy you’re here writing, Ashley. I haven’t read anything from you that hasn’t moved me. Honestly, tears sprung to my eyes reading this. Not because of your relationship to your grandmother, who sounds kickass, or your relationship to clothes, which sounds enviably awesome, but because you frame your words in such a way that they pack an emotional punch that never feels inauthentic. I just simply love the way you write and the way you look at life and yourself.

    Also, please write many books?

  31. Rosie says...

    This essay is so beautifully written. You’re inspiring me to clear out my closet and choose clothes I really like!

  32. I love this so much! Your grandmother’s words are the best fashion advice I’ve ever read! I’ve kind of gleaned the same wisdom from my now 5-year-old. She just wears what she loves, and she beams. It’s inspiring and liberating to know it’s that simple.

  33. Heather says...

    The truth of “I literally spent years like, ‘I hope nothing fancy happens!'” had me laughing out loud! Ashley’s writing always has me smiling and crying within a few paragraphs of each other – she has a beautiful and honest voice and I’m so glad she’s a part of your talented team.

  34. Lauren says...

    I am a long time reader of this blog and this will be my first time commenting! I have always wondered how I should approach what my “style” is, I often feel I am all over the map and tend to overthink what I should go for… your message was wonderfully said and has such clarity. It really hit home and is brilliantly written. I can already tell this will be one of those articles that I will always remember. Thanks for the advice that this 24 year old won’t soon forget.

    P.S. Go grandmas of the world! What would we do without them?

  35. Jennifer says...

    i’d love to see a post on the perfect leather jacket!!!
    i am absolutely convinced that my life will get exponentially better once I get one :) it feels like a staple!

    • Joanna Goddard says...

      good idea!!

  36. Katie says...

    This is such a lovely piece! Your voice is a great addition to this site and what you’ve written here is meaningful for any reader.

  37. Larissa says...

    This is so beautiful. What a testament to your grandmother!

  38. I have a grandmother who loves bright lipstick too. This made me want to wear my ripped jeans and a tee shirt-easy clothes and easy style. My favorite thing. Thank you for this! Merry Christmas.

  39. Shannon says...

    This is really touching.

  40. Kathryn says...

    I may more physically resemble some of the incumbent writers on this blog, but my style experiences were so much more reflected in this piece. Loving the new voice on the blog, and can’t wait to read more.

  41. Clare Agra says...

    Love this! Thank you for sharing.

  42. Anna says...

    I’m so happy you are here.

  43. Sarah W says...

    Beautiful story. Thank you Ashley!

  44. j says...

    lovely, thanks for sharing.

  45. Kim says...

    I love your article, thank you for sharing. You look so happy in your picture.

  46. Melissa says...

    Loved everything about this essay! It was a beautiful read and so refreshing and inspiring! I want to clean out my closet right this minute!

  47. KV says...

    Ashley, you rock! Your grandma would be so, so proud of you.

  48. Robin says...

    Love everything about this piece. So excited that Ashley has joined the COJ team!

  49. Emily says...

    I clicked over to read about your (awesome) style but was unexpectedly in tears by the bed! I’m inspired to re-evaluate how I should dress to my own happiness. I never comment here (after years of reading!) but I just had to say that I’m so happy your voice and stories will be on CoJ! Welcome, Ashley!

  50. Vicki says...

    “Happy looked great on me.” !!!

  51. Christina says...

    Yesssss!!
    You are a warm spirit. Thank you.

  52. Kristina says...

    beautiful!

  53. Meg says...

    Loved this. At 40 I’m just learning to dress for myself and wear what makes me happy. Who have I been trying to impress all these years??

  54. Carrie says...

    What a lovely, wise essay. Thank you!

  55. brianna says...

    The Cup of Jo team is killing it right now. This piece was so inspiring and lovely. Thank you for sharing, Ashley.

  56. thank you for sharing this. I too had a similar relationship to my grandmother before she passed away. it felt like i was reading somewhat my own story. one thing that is a little different is that I i am going through some health issues right now and one of the “side effects” is that i gained a lot of weight. in a year i went from being 120 to 200 that is a huge change for me and it had me depressed for a long time. I am barely able to say that I want to get out of that, i am not very aware of how to dress my new body yes I would like to slim down but right now this is me and i should love myself no matter what but i too am learning how to feel comfortable in new clothes which is hard but hopefully i too will find my way like you did.

  57. Tricia Wu says...

    This was so relevant to me – I feel like I’m in the midst of my revolution too. I was never able to explain it well so I’ll be sending this article to friends!! I have been following Jo for years and years, since your first or second year! I think this is one of my most favourite articles from cupofjo (this and anything from motherhood around the world). Ashley, you’re amazing.

  58. Sirena says...

    A very special piece! My grandmother, Nana, was an inimitably stylish lady. So elegant and effortless and everything carrying the unmistakeable stamp of her personal style. When I think of my life today, the highest bar I have is, Would Nana have approved? Thank you for sharing this!!

  59. Danielle says...

    What a beautiful story. I adore Ashley’s writing and how you can truly feel her words.

  60. Stacy says...

    I love this so much. Women get more beautiful from the inside out, as time goes by, and it sounds as if your grandma knew that. So glad that you found your style and only wear what feels good to you! The pic of you and your grandma is priceless; the love emanates.

  61. Maggie says...

    “Happy looked great on me.” Oof. Givin’ me the feels. So glad you’re here, Ashley!

  62. LV says...

    <3 <3 <3

  63. Becky says...

    I loved everything about this. Thank you so much; I needed this wonderful lesson today.

  64. Kristina says...

    Love this. The writing, the story, everything. Just beautiful.

  65. Margo says...

    Totally cried. Lovely piece about finding love for yourself and letting your grandmother show you the way!

  66. K.C. says...

    You are such a talented writer, and your grandma sounded like a wonderful and inspiring person.❤️

  67. Nora B says...

    I love every word of this so much. All of it is truth, regardless of what our bodies’ shape is. Thank you, Ashley! So looking forward to more you on this amazing site.

  68. Brittany says...

    This resonated with me so much- I’m reading this through tears in a hotel room in Toronto, where I arrived today for my grandmother’s funeral. My memories of shopping with her are some of my favorite. Thank you for this and for that reminder!

  69. Sarah says...

    I loved this so much. I’ve been big since I was born – I have no idea what it would be like to live in a thin body. I’m an expert at living in a big body, though! I decided a long time ago to only wear what makes me feel comfortable and at ease. It was one of the best decisions I’ve ever made!

  70. Amy says...

    I think you’d like Gwynnie Bee – it’s like Netflix for plus size clothes, and they have brands such as Elloqui. I used the service for about a year, and ended up buying many staple pieces for my closet which I still love. I ended up quitting the service, because their style evolved into one that didn’t resonate with my style anymore – but I know a lot of people still love them, so you might as well.

  71. Lizzie says...

    What a beautiful and poignant essay. Thank you for sharing this story with us, Ashley. Loved it.

  72. jeannie says...

    I love your philosophy about style. Most of all I love that last picture of you and you grandmother – beautiful! She would be so proud.

  73. Lynn-Holly Wielenga says...

    I recently lost my grandmother, so this post was especially poignant. She also had a vivacious personality. Thanks for your sweet words Ashley. What an encouraging post! Happiness is definitely a great look.

  74. Julee says...

    I’ve been so impressed with you and your writing, Ashley. Your work leaves me with a sense of joy- yours and my own.

  75. Steph says...

    Spot on! (And lipstick always fits!)

  76. Kia says...

    Thank you for sharing this!!!

  77. Ramona says...

    What a sweet story. I didn’t grow up with fashion encouragement from either of my grandmothers or my Mom. Being tall, clothes never have fit me quite right. I’m in my 50’s now and it’s still so very hard to find clothes that aren’t ‘too old/too young/within my budget.’ I have found a few outfit formulas that work for my body type and I find that many times, great hair/accessories can make an outfit. When I do find great pieces, I tend to buy them in multiple colors. I have splurged on a few wardrobe classics which have been a great investment. However, some of those classics have been found at Gap/Old Navy which offers Tall sizes! Amen!

  78. Renee says...

    So, even before reading this, I thought “ooh, it’s Ashley!” Such a lovely essay, and thank you for including the picture at the end.

  79. Kara says...

    Very sweet story!

  80. Jill says...

    What an amazing writer you are, Ashley. I am so glad that your voice has joined cup of Jo. Thank you for this beautiful essay! I can’t wait to read more of your writing.

  81. Abi says...

    Oh Ashley, thank you.

  82. Robin says...

    This is beautiful. Just…wow. Thank you for sharing your story.

  83. Claire says...

    I can’t think of any other description of style that is so simple and so liberating.

  84. Jennifer says...

    Ashley’s voice is so essential. This is so beautifully written… thank you for highlighting how important what we wear can be!

  85. Rachael says...

    Ashley I’m so glad you joined the Cup of Jo team! This story was poignant and insightful- a joy to read! Thanks for sharing!!

  86. As a fellow plus size women, this rang so true. I truly hated myself until I realized what I was seeing on social media all the time, girls, bloggers, models, people that looked nothing like me. So I did my research, found brands that catered to plus size women and then looked at their tagged pictures and would follow women who looked like me and whose style I admired. It changed everything! I realized I didn’t have to squeeze into clothes I hated. So eye opening into self acceptance.

  87. Sarah Yeung says...

    This is such a beautiful voice and story and as a woman of color I teared up thinking that someone like me would be telling it on such a huge platform. I don’t think COJ has ever had a person of color as part of their permanent writing team. As a loyal reader for many years I have always felt this sense of loss from not feeling that perspective represented, despite my love of the many talented writers that have come through. I cannot properly explain it but it is so meaningful to hear your voice, it feels like a balm to the soul.

  88. Yes to this! Comfort with ourselves (in and out of clothes) is a hard thing to achieve. Yes to wearing what you like ( but being grown enough what’s appropriate for the occasion!). My fiance teases me when I wear my faux fur leopard vest but I don’t give a damn. I love it.

  89. Michelle says...

    So happy to have you on CoJ, Ashley! This was a beautiful piece and reminded me of my own grandmother and how she inspires my sense of style. <3

  90. Julie says...

    Beautiful piece and touching story! Your grandmother seemed like a real gem.

  91. Yeesheen says...

    My god, what a great piece of writing this is. “I spent years of my life believing my best looks were behind me, but now I’m in the midst of a body revolution.” Few writers would construct that sentence in that way — and it really, really works. Ashley, you are a talent. Can’t wait to read more of your work.

  92. Emma says...

    Thank you, Ashley!!! This is so beautiful.

  93. Tiffany Cain says...

    This is a good reminder of the joy fashion brings me. I forget that when I feel chubby or old. Love that photo!

  94. love this! your grandma is definitely smiling down on your great style now ;)

  95. Diana says...

    So many gems in this article.

    My first tear dropped when I read, ” I wanted to smell like her when I said goodbye.” By the time I read this line:”…and when someone looks at me now, I know they’re seeing the version of me I chose. Not the only version I had access to,” I was bawling.

    Thank you, Ashley, for your words!

  96. Katie says...

    Sigh. This is so lovely, and I needed this. My dad passed away a few months ago, and I’ve just not been living my best body-life (not eating great, not exercising, etc.). It’s been hard enough pumping myself up to go out and be happy with friends, but harder still to figure out what I want to wear. On a particularly low day, a coworker congratulated me on my pregnancy (not pregnant – THANKS). Anyway, I think it’s time to spruce this lady up and stop worrying about my exact shape.

  97. Julie E says...

    Hot damn this is an A+++ post!!

  98. Shauna says...

    More Ashley, please!

  99. This. Is. Everything. Ashley, your post came at a time when I was giving up on clothes and style. I couldn’t figure it out and because I am a plus size woman, I thought I’d have to spend my time in clothes that cover me up. I am so grateful you shared clothing companies that are accessible to plus size women. Your article sparked a light in me to try again, to not give up and to take pride in the adventure. Here’s to style and loving our bodies, exactly as they are right now! xxoo

  100. Monica says...

    Reading this, then seeing the picture of you and your grandmother has put a lump in my throat. I can tell we had similar relationships with our grandmothers and I would like to thank you for bringing up to the surface such strong emotions.

  101. Valerie says...

    Ashley, I enjoy all your pieces so much. (I also think of both my grandmothers when I put on a bright lipstick, so that especially hit home.) Thanks for sharing this story — and some good advice from what sure sounds like an awesome woman — with us.

  102. Katie says...

    Loved this story and the photo – my grandmother and I are also very close, and she is forever buying me clothes. “Fashion show!” she and my mom will say, when they buy me clothes. I used to resist their style when I was young…now the three of us basically have the same wardrobe :)

  103. Kate says...

    Thank you! Beautiful essay.

  104. Christine says...

    I loved reading your words! Thank you for sharing this beautiful story, I can relate to so much of what you described! My grandmother loved matching her shoes and handbags. Whenever I buy a pair of shoes, my mom tells me I’m just like my grandmother; I love that! I spent so many of my weekends as a kid combing the sale racks of stores with my mom. That is still one of my favorite things to do with her. To this day, the sale section of a store is still the first part I visit.

  105. De Jacobsen says...

    Ashley is so gorgeous.

  106. Andrea says...

    This is so inspiring & relevant to me & my post baby #2 body. I definitely have a ton of clothing in my closet that do not bring me joy, that I just wear. I find myself not wanting to be seen when I’m out & about because I don’t feel good about the way I look & my closet reflects it. Obviously that need not be the case. Thank you Ashley! You are a light!

  107. Audrey F says...

    Ashley – Your grandmother sounds fabulous. Thank you for sharing. Now I’m motivated to go clean out my closet for the New Year!

  108. Paula says...

    Beautiful words, and a inspiring message. Keep shinning.

  109. Christina says...

    I have never felt compelled to write a comment until now – this was a lovely, beautiful post, I’m trying to decide if I love it more than Ashley’s first post about finding and loving her fiance (which still haunts my heart and mind with its honesty and beauty). I am so excited to continue to hear her voice and her stories – who would have thought Cup of Jo could get EVEN better!! I hardly thought possible :)

  110. Lee says...

    As a child of the Depression, my grandmother was thrifty and never bought something she didn’t need, but also never threw anything away. After she passed away, we found clothing in her closet that she had, no exaggeration, not worn since the 1940s. As we sifted through the endless blouses and trousers in neutral colors, the only clothes most of remembered her wearing, we were surprised a couple times, but never as much as when we stumbled upon a violently orange/maroon/lime green/pink/turquoise paisley dress with a thigh high slit and matching hot pants. My aunts nearly fainted. The consensus seemed to be “she didn’t ever WEAR this, right?” Weeks later, when people had moved on to sorting photos, a single picture of her in the dress was uncovered. She’s at some work party, grinning and happy and clearly completely comfortable. Just thinking of it gives me courage, and a strong desire to dress myself in a way that will shock my future grandchildren.

  111. Alisa says...

    I plan to forward this to every woman I know. Well said!!

  112. Alyce says...

    I love Ashley’s storytelling. So glad she joined CoJ.

  113. Lilia says...

    Ashley, this is beautiful! Like most women, I have also spent a good part of my life not feeling quite happy with my body (too flat-chested, too round-bellied, too short-legged, blah blah). In my case, it took having children to appreciate just how strong, capable, and beautiful it is (wish I’d had the realization sooner, but alas!). I am also now trying to dress my body with clothes that really make me feel great — it feels vain at times, but when you feel great about yourself, you radiate better energy. Anyway thank you for this lovely article. Your grandmother sounds like she was an amazing woman, by the way. :)

  114. Mallory says...

    “. . . my Midwestern hips actively revolted against the seams of their low-rise jeans. ” No truer words have ever been spoken.

  115. anja says...

    how sweet and encouraging. i have tears in my eyes.

  116. this is a beautiful tribute to your grandma and reflection on self discovery and style. Such a warm and engaging style and lovely, lovely essay Ashley.

  117. Emily R. says...

    I love this more than most things I’ve read on most blogs recently. Ashley, the beautiful memories about your grandmother coupled with your own blossoming into your style are just wonderful. I loved reading this, I loved hearing about your grandmother, and I am so happy you found a way to dress that makes you happy. Inspirational. I just sent this to my twin sister, who also seems to struggle with dressing her plus size body and embracing a style of her own.

  118. Erzsi says...

    I love this story, and I love Ashley’s reminder that memory and nostalgia and association can bring deep meaning to even seemingly simple material things like a wardrobe. These are such powerful forces–remembering my roots and the people I love always makes me feel more beautiful, too.

  119. AzureSong says...

    You’re such an amazing writer Ashley! This piece is so touching. I love the part challenging the notion that “your best looks were behind you.” I know you were referring to weight, but it is also applicable to aging. As a person in my mid 40’s, it’s definitely a nagging thought that I try to push away. Plus, the picture of your radiant grandmother helps a lot!

  120. Jen says...

    Your voice is so special. Thanks for your story, it made me tear up!

  121. Tara says...

    Thank you for sharing. Your grandmother sounds like she was an awesome lady, and I bet she’s cheering on every swipe of bright lipstick and each joyful thing you do.

  122. So beautiful. Thanks for sharing.

    Also, I love hearing from a fellow Indiana girl :)

  123. Anita says...

    Ashley, I just love this so much – beautiful writing, beautiful story, beautiful message, beautiful people – I will reread and reread until it sinks in for me….

  124. Yasss!!!!! As many posts as possible from Ashley please! was too excited to wait to comment after reading

    • Abbie says...

      Yes!!

  125. This essay is so tender and beautiful. Love the pic of you and your grandmother. So thrilled to have your voice here, Ashley.

  126. Karina says...

    this, oh this Ashley, just made my day. as a curvy woman this resonates so much with me, and you’ve brought a smile to my face when I felt very down and uncomfortable in my own skin today. thank you for these words.

  127. Your grandmother sounds like she was amazing and I’m glad that you have such wonderful memories of her. I have two sisters and my grandmother took us clothes shopping a lot, too. She would always buy us Easter dresses and shoes. Her style was inspiring and she helped me to stop biting my nails in middle school by giving me weekly manicures. Thank you so much for sharing this beautiful story. I relate to it so much.

  128. jade says...

    I have spent the past year going through and clearing out my wardrobe- trying to figure out what I feel most comfortable in and it has been tough! As someone whose struggles have mirrored Ashley’s in a way her words “Who wants to go out when you know you won’t feel good when you get to wherever it is you’re going?” feel too close to home. I look forward to reading more from Ashley.

  129. Heather says...

    So beautifully written, it made me think about my own amazing Grandmother.Thank you Ashley.

  130. Akshara says...

    I loved reading this, Ashley. I kept nodding my head to the challenges you faced in dressing your body (as I have and continue to have). Thanks for the advice & a good read – your grandmother sounds like a true gem! I can’t wait to see what else you write for Cup of Jo!

  131. Elizabeth says...

    ok, i’m going to have to learn to not read ashley’s body positive posts at work. tears.

    as a teenager, i once read you’ll never like the clothes you are wearing if you don’t like the person in the mirror wearing them. sounds corny but it really stuck with me.

  132. Kelly says...

    I loved this! What beautiful writing.

  133. As someone who is learning to love the body I have not the body I wish I had, this resonates with me so much. I agree with it all. I have just one thing to add: when you know how you want to dress, you have to buy things that match the way you want to dress. I have always wanted an ‘edgy’ style and a light bulb finally went off for me when I realized that the only way I would have that edgy style I wanted is to only buy things that fit that style I was after. Such a ‘duh’ moment, but personal style really is built one item and accessory at a time.

  134. cms says...

    What a beautiful essay. Thank you for that.

  135. KL says...

    One of my most poignant memories was the day I wore an outfit my mom had given me for my birthday. I was young, probably in the fifth grade, and the outfit was a bright blue (I mean BLUE) sweat suit with red, green, yellow, and orange bold strips on the sweatshirt. I loved it the second it came out of the gift-wrapped box. I wore it the very next day, and in my music class, the girl next to me turned and said, “your outfit is ugly, why are you wearing it??” and, immediately embarrassed, I replied “I played a fun game this morning and picked out my outfit with my eyes closed!” She thought it was a funny game and we both laughed about it. When I told my mom later that day, she said, “But, who cares? Wear what you like!” I never wore that outfit again. At 30, I honestly still feel so ashamed that that was my response. For years, until this year really, I dressed in a way that didn’t express who I “really was.” When I turned 30 in October, it was like a lightbulb went off. “Who cares?? I want to wear what I want to wear!” So I bought very androgynous clothing! Loose fitting pants that still have style! Boxy tops! Brown mascara (dear God, why didn’t I find out about brown earlier in life…)! My closet still isn’t filled with every piece that feels like “me” yet, but it’s on its way, and ironically, I’ve never received so many compliments on my “style” until now. Funny how that works, huh?

    • That’s a great story, KL! I’m sure your 5th grade outfit was amazing, too.

    • Stephanie says...

      I know this isn’t PC of me but I want to punch that girl sitting next to you in music class.

      I have two young daughters (4th and 7th grade)just developing their own ideas about style (and Life!) It breaks my heart when I hear some of the cruel ways girls this age speak to each other, although it opens up discussions with my daughters on how they want to be spoken to and how they should speak to others.

      Congrats on finding your style! 30 is young. I’m 44 still working on mine. ;)

      Cheers! (And I want that blue sweatshirt now!)

  136. Jill says...

    That photo of Ashley hugging her grandmother is so beautiful!

  137. Meghan says...

    What a beautiful story! Funny how the things you “LOVE” you end up wearing forever. I hope you were able to keep some of those items your grandmother loved. She sounds like one fabulous lady!

  138. I love this – what could be more important in a role model than teaching you how to love yourself a bit more and be the version of yourself that makes you happiest. Wonderful!

  139. Taryn says...

    Ashley, this is a lovely piece. So glad your voice is part of this space!

  140. Celeste says...

    “In that moment, I liked the way I looked more than I ever had before. In a striped grey dress, a black cardigan, and the brightest lipstick my mouth had ever worn, and on the saddest day of my life, I felt beautiful. I was devastated, but so very happy to be alive.”

    Then, this? “I modeled my new clothes for my fiancé, and watched his face light up not just because I looked good, but because I looked happy. When I glanced in the mirror, my face brightened as well. Happy looked great on me.”

    Oh, tears. Thank you, Ashley, for sharing your story about finding your style. Your grandmother sounds lovely, and so does your fiancé! Wishing you all the best as you get ready for your own fancy day. You’re going to look beautiful. <3

    COJ: This essay sparked an idea I'd love to get your thoughts on! How do we talk to girls about this? I have a Girl Scout troop, and we're constantly navigating this very thing. Thanks!

    • Gen says...

      Hear hear for that suggestion, Celeste. My daughter is five and has strong opinions about what she likes to wear and NONE OF IT has to do with what other people think. How do I keep her in this mind state (or at least in touch with it) when society is waiting to crush it out of her?

    • Annie says...

      Great idea for a topic worth exploring. How do we talk to younger girls about this? I don’t want them to have to wait as long as it seems many of us have waited to feel comfortable in their skin/style.

    • Chelsi says...

      I second Celeste’s comment! How do we talk to young girls about this? I feel like girls are so conditioned to look a certain way from such a very young age (thanks Disney!). I’d love to hear more about guiding girls down the path of what’s important vice looking a certain way.

  141. Auste says...

    Goodness, i love her writing. Makes me miss my ever-stylish grandmother, too. Last year at her funeral, my mom, aunts, cousins and I all wore bright red lipstick in her honor, and each of us wore a piece of her jewelry. We all looked, and felt fabulous. She would’ve loved it.

  142. Renee says...

    I am also in the midst of a body revolution. I want to try new things. This article has now given me the courage to wear my grandmothers vintage coat from 1932, that my mother gave to me 5 years ago. Great article. Thanks Ashley!

  143. CL says...

    Oh, this warms my heart. Beautiful piece.

  144. Andrea says...

    Beautiful! I needed to hear this. Currently trying to figure out how to dress my new post partum body.

  145. So so excited to be reading more of Ashley’s writing! Like your other cup of jo essay, I was skimming along a post about fashion when your words took my breath away. Your writing always inspires me to sit and enjoy the piece instead of rushing through and I loved your outlook on fashion and style. The connection to your grandmother is so beautiful, and I love how you incorporated your boyfriend’s happiness while not implying that your style was for him (his happiness at your happiness). Beautiful and lovely, thank you for sharing.

  146. This is beautiful and full of truth. I couldn’t help but tear up when I got to the photo at the end.

    • Lily says...

      Me too!

  147. Marion says...

    Ahhh! I NEVER post on anything but I had to post here and say that this article literally gave me goosebumps. What a beautiful woman and writer to capture what it feels like to gently reassess your relationship with your body and your style and make changes towards happiness. I loved this so much! So happy you’ve joined the cup of jo team!!!

    • Martha says...

      My feelings exactly! Bravo, Ashley!

  148. Hanna says...

    This is lovely advice and a beautiful story, Ashley. Grandmothers are so special. xoxo