Style

A Week of Outfits: Ashley Ford

A Week of Outfits: Ashley Ford

Ashley Ford is a writer, editor and speaker — and she also has killer style. “I look pretty bold naturally, and for a long time I was trying to hide that,” she says. “Now I’m not. These days, I feel like I look the most like myself that I ever have in my entire life.” Ashley lives with her boyfriend Kelly, in Flatbush, Brooklyn. Here, she tells us about five outfits she wore in a week, and the bikini she’ll debut on her upcoming vacation…

A Week of Outfits: Ashley Ford

Dress: Universal Standard. Earrings: vintage, similar. Lipstick: Bite in Aubergine. Heels: Via Spiga, similar.

Universal Standard has the kind of minimalist clothes I like — but they actually come in my size, which is beautiful for me. I don’t want to wear something that makes me look smaller or bigger; I just want to wear something that looks good. My favorite part is how the hem comes up on one side, and I love this color yellow. That’s the best thing about being black: there’s no bad color! Nothing washes me out.”

A Week of Outfits: Ashley Ford

Dress: Banana Republic, similar. Earrings: similar. Bag: Fossil, similar. Flats: Banana Republic, similar.

“When I first moved from Indiana to New York, I was nervous to go shopping. I had always thought of New York as this extremely fashionable city. I didn’t have the budget, and thrifting is hard when you have a bigger body. But I walked into a Banana Republic, and this dress was in the clearance section. I couldn’t believe it was in my size and on sale for $14. It made me feel professional but also pretty and flirty. If you want a deal, don’t be scared to dig. Try multiple sizes because sale pieces are often sized weirdly. Don’t give up, because your next favorite piece is probably still out there for $3.”

A Week of Outfits: Ashley Ford

Sweater: Vince Camuto, similar. Jeans: J.C. Penney. Earrings: vintage, similar. Belt: Levi’s. Sandals: Target.

“These flower earrings were my grandma’s; she passed away a few years ago. She was my best friend. Nowadays, whenever I do something that’s a goal for me, I wear these earrings and bring her with me. As I’ve grown older, I’ve gotten to know my style better. I carried a picnic basket as my purse in middle school. It sounds cute; it wasn’t. It was an actual picnic basket, like a Dorothy-on-her-way-to-Oz situation. When I was in high school, Sex and the City was also super popular, so I tried to do the big flower pin like Carrie did. I was like, I want to be a writer, this is the way to do that, right?”

A Week of Outfits: Ashley Ford

Dress: Gap. Earrings: similar. Necklace: similar. Flats: Banana Republic, similar.

“This was the exact dress I wanted for summer. I felt like I went into the store, and they were like, Oh, we’ve been waiting for you. It would be perfect for a vacation. Traveling as a young person never actually happened for me. There weren’t enough resources, or enough time, or enough opportunities. At some point, I realized I had to figure out how to do it for myself. Kelly and I decided travel was going to become a priority in our finances and relationship. And this May, we’re going to Italy for two weeks — it’s our first trip together. Neither of us has been there. It was very important to me, especially on this first trip, that he wasn’t showing me the world, that we were experiencing it together.”

A Week of Outfits: Ashley Ford

Dress: Gap, similar. Earrings: similar. Shoes: Nike.

“I’ve spent a lot of time having this mental list of things that I was too fat for, too black for, too poor for. But it got boring. You can’t live your life like that. If you try hard to avoid disappointment, you also avoid excitement. In Italy, we’ll be staying in Cinque Terre. I have a one-piece swimsuit, but I’m in this phase of my life where I’m trying to embody myself and look the way I feel. I had been looking at bikinis for a while but felt really, really scared to pull the trigger. Then I saw blogger Gabi Fresh launched her line Swimsuits For All. There was one bikini with a ruffle top and faux-denim bottom. I was like, ‘Yeah, that’s me!’ Now that I’ve stopped trying to control everything, I’ve ended up living a life where I get to feel excited, almost all of the time. ”

Thank you so much, Ashley! You are awesome.

P.S. More women share their outfits, and how to prevent blisters from shoes.

(Photos by Christine Han for Cup of Jo. Interview by Joanna Goddard and Stella Blackmon.)

  1. Loved your outfits and relationship article. I sent it to my daughter!

  2. Susie says...

    Beautiful!

  3. Gemma says...

    Hi,
    Loved this! where are the yellow curtains from?
    thanks!
    Gemma

  4. pam says...

    I think you are really pretty and look so friendly.

  5. Jen says...

    Ashley is remarkably stylish, and I love her outfits! When I looked at the captions, though, I saw the names of stores that are happy to sell me clothes online (with the shipping costs associated with that) but don’t sell my size in the stores. That’s what I call the “plus size penalty” – the extra time and money we spend not being able to browse through racks and simply try on clothes in the store to choose what we want to buy. Instead, we have to guess based on website pictures, pay shipping charges unless we spend a lot, and spend more to return what doesn’t fit, or drive to the store that didn’t want us there to begin with.

    Ashley looks terrific in everything she has on, and bravo to her for her style and her attitude. Just know that for big women, pulling together those outfits is a lot of work, often at a higher price, and means having to shop at stores that want your money but don’t want your body visible to their other customers.

    • Elizabeth says...

      Mic drop. Whoever you are, Jen, let’s be friends.

  6. Gaby says...

    Oh my goodness – love her every outfit!

  7. Caitlin says...

    I just wanted to put out there that, months after reading this, Ashley’s profound comment, “I’ve spent a lot of time having this mental list of things that I was too fat for, too black for, too poor for. But it got boring. You can’t live your life like that,” has become my daily mantra. It’s so simple yet has totally changed how I shop (something I love) and look at myself (something I really struggle with). Thank you for giving us such beautiful content, authors, and badass women to learn from and have great impact on our lives.

    • YES! I found myself thinking this very thing today and had to look up this article again just to reread that quote! Thank you Ashley and COJ!

  8. Jordan says...

    She is chic! I will copy every single outfit. Her shoes really make a statement! Thanks for the ideas!

  9. Suzy says...

    Love Ashley’s style and personality! Her confidence exudes and I envy that. The chambray Gap dress caught my eye but dang I caught this post too late! :/ So classy.

  10. I love how simple her style is. She adds a pop here and there, but overall it’s so beautifully, wonderfully relaxed and put together. Not that Ashley’s style is like this at all, but I used to give myself a hard time about not putting as much effort into style as it seemed other women were doing. But I realized that some people, and this even includes men, appreciate the art of an outfit in different ways (some may not even care at all, either). The biggest lesson I learned in style was simply figuring out what mine was and staying true to that, because it would represent who I was as a person whether I wanted it to or not, so I may as well get more intentional about my wardrobe choices. Once I understood that, I was better able to determine the articles of clothing I would wear most and longest and feel happiest in over the ones that gave me instant gratification in the moment but would be quickly discarded after a few wears. It’s also easier for me now to buy clothes that can be worn between work and play and mixed for different outfits because I now understand my style, something that was never easy for me. Anyway, I went on a spiel. I should probably just write a blog post about it. :)

  11. Bethany says...

    I’ve loved nearly all of the week of outfits posts, but this is my favorite. This woman has style and is owning. it.

  12. Natalie says...

    “If you try hard to avoid disappointment, you also avoid excitement.” Sometimes you find just the thing you need in an unexpected place. I love this series, and this one was an extra special read for me.

  13. Monica says...

    I’d wear anything she wears!

  14. Shannon says...

    Ashley you look hot in your last look. Love that dress! I also love all your book recommendations on Instagram ????

  15. Kelly Herzberg says...

    Ashley — you are a badass chick! Eff yes to life! You inspire me to be my most badass self. Thank you! XOXOXOXO

  16. I’m such a huge fan of Ashley – I’ve been reading her work for a long while now. Actually, whenever I have writer’s block, re-reading a few of Ashley’s essays are a foolproof way for me to feel inspired and to pick up my pen once more. Anyway, point being that I absolutely LOVE the features that she’s done here on COJ! It’s amazing to know that someone you look up to writing-wise is also a phenomenal person (and dresser)! Keep workin’ it, Ashley!

  17. Sarah says...

    Girl got chic!

  18. Midge says...

    This is so inspiring. YES!

  19. Kathleen says...

    GORGEOUS!!! You have my dream body and look!! Just fabulous. xx

  20. Thao says...

    She’s luminous!! That yellow dress is like sunshine captured. Love her style.

  21. sarah says...

    THANK YOU for the lovely post. Ashley, I love your style!

    Jo — keep posts like this coming often!

  22. Cindy says...

    She looks radiant!

  23. You look fabulous Ashley! I especially love all of your brightly colored shoes. Keep being bold – it suits you!

  24. Thank you for sharing your amazing self with us and your wonderful sense of style! You rock!

  25. Thank you! This was a woman I could relate to so well even though appearance wise we are VERY different as I’m VERY Irish looking: fair, freckled, reddish hair and greenish blue eyes. I’m not what i would ever consider “bold looking”, either. I LOVED that she commented on having “a bigger body” and felt frustrated with thrift shopping…. and shopping in general. Me, TOO! But, as I’ve aged (40 yrs old), It’s soooo difficult to be PLUS sized at a 14/16. I didn’t consider myself plus size but when I shop, those damned jeans just don’t button. I surely could lose a few pounds, and i’m trying…but my life is good and I, too, have limited myself for TOO long.

    I even bought that chambray mid dress from GAP for my recent birthday cruise. Life is too short to not celebrate.

    Bravo!!

  26. Beth says...

    When you talked about your grandmother’s earrings, the tears started rolling…Thanks for a lovely post.

  27. Cerises says...

    So inspiring.
    I love Ashley’s style and outlook on life. Thank you so much this gave me a smile and somehow made me feel good about myself (which was the same feeling I had got from reading her essay).
    And I am so in love with that yellow dress that I am considering ordering it from France ;-). Thank for making me discover universal standard.

  28. Gina says...

    OH. MY. WORD. Love this post so much. It’s so great to see someone on one of these features who shops at places more in my price range (poor grad student here). And Ashley, YOU. ARE. GORGEOUS. Love your style and all the fun colors!

  29. AnneE says...

    LOVE your style!

  30. How great to see a young woman who has already figured everything out for herself style-wise. She’s only going to look more amazing as she gets older because she has confidence and a great eye and both will continue improve with time. She will always have the best swimsuit. Her closet will be legendary.

    I want all of her shoes! I’d also like to be her when I grow up, but unfortunately I’m already about twice her age.

  31. Leah says...

    Love her. Love her outlook. Love her style. Love her smile.

  32. Love Ashley’s bold and colorful style! I want to rock more colors this spring and that yellow dress is fabulous!

  33. Erin says...

    Ashley, what a style icon you are! When you are in Italy go for the bikini!! I went to Cinque Terre 2 years ago and I only brought a one-piece out of habit and, honestly, some unhealthy body shame. When I was finally on the beach in Levanto, I looked around and realized every type of woman and man was there reveling in the sun and water in tiny bathing suits! I regret not taking the moment to be braver. I dream of going back, and next time it will be in a bikini.

  34. Jen says...

    It’s really fun seeing someone with my same body type/size and preference for plain clothes!

    Really want the first two dresses!

  35. Blaise says...

    Thank you so much for featuring options for plus-size clothing–you should do this all the time! :)

  36. Michaela says...

    I loved the yellow Universal Standard dress from the first picture and was initially disappointed to discover that they don’t carry my size. Then I realized that my tiny disappointment in this one scenario probably doesn’t compare to the experiences of many women who routinely can’t find their size when shopping. It was an unexpected (and welcome) wake up call. So shout out to Universal Standard for making good looking clothes for women in larger sizes and not feeling obligated to worry about smaller women – plenty of other stores are covering the small clothing market!

  37. Liv says...

    Gosh, she is really the best. Thanks for this piece, Jo, and thanks for being such an inspiration, Ashley!

  38. Mandy says...

    Love every outfit, very jealous of yellow dress which is a color I cannot wear. I prefer bikinis and subscribe to strict “bikini body” policy: find a body, put a bikini on it.
    What are glasses??? Best accessory, they are perfect on you Ashley. (Love you always on Women of the Hour podcast.)

  39. What an inpspiring out look. Thank you for reminding me. Also that bikini is going to look amaZing.

  40. Teresa says...

    Gorgeous inside and out, bold fashion, refreshing candor. Love her style.

  41. Linda Z says...

    Love her beautiful smile… she is darling! The comment about Dorothy and the picnic basket made me laugh!! :) That’s something I would have done!

  42. Amie K says...

    “..Now that I’ve stopped trying to control everything, I’ve ended up living a life where I get to feel excited, almost all of the time.

    Beautiful.
    I’m a Virgo so letting go of the control piece is hard. I have been thinking about this concept a lot, for a lot of reasons, and in a lot of capacities lately. Thank you for this. I needed to see it. Hear it. Know someone else feels it. You’re lovely, thank you!
    Enjoy Italy!!!!!

  43. Trish O says...

    “I’ve spent a lot of time having this mental list of things that I was too fat for, too black for, too poor for. But it got boring. You can’t live your life like that. If you try hard to avoid disappointment, you also avoid excitement. In Italy, we’ll be staying in Cinque Terre. I have a one-piece swimsuit, but I’m in this phase of my life where I’m trying to embody myself and look the way I feel. I had been looking at bikinis for a while but felt really, really scared to pull the trigger. Then I saw blogger Gabi Fresh launched her line Swimsuits For All. There was one bikini with a ruffle top and faux-denim bottom. I was like, ‘Yeah, that’s me!’ Now that I’ve stopped trying to control everything, I’ve ended up living a life where I get to feel excited, almost all of the time. ”

    THIS…you have put into words what was in my soul. I don’t know if it is my age or just my reaction to the the world, but I am done with my worry about what other people think. DONE. It is too hard and just not worth it.

  44. Asri says...

    Ashley! Her piece on dating Kelly has stuck with me SO MUCH. I shared it with my friends and revisit it often. Her writing is vulnerable, intelligent, and fun– trifecta of delight! I was thrilled to see she had an outfit post. She is STUNNING! I’m hoping one day to be able to express myself this well. ASHLEY! We love you!
    Cup of Jo team– you guys have elevated lifestyle blogging in a way I haven’t seen with any other blog. Posts about fashion, beauty, shopping, and other things I used to judge as “frivolous” (but loved in guilt) are lovely and meaningful.
    xoxo

    • Didn’t make the connection at first, thanks for pointing it out! That article she wrote was beautiful and I resonated with it so much. Glad we get to see the beautiful woman behind the story!
      Thanks Ashley and cup of jo – y’all are awesome.

  45. Meghan says...

    Love, love, love Ashley’s style!

  46. Emily Connelly says...

    I love your outfits and all you have to say about them – beautiful! Have a wonderful time in Italy! We went after working together and saving up money for a while, and it was definitely worth it. Dig around for all the best pizza in Naples, it’s the best kind of research.

  47. pam says...

    beautiful face, figure and style!

  48. Caroline says...

    The best part about Ashley is her smile! It really lights up a room. Lovely lady and I hope she enjoys Italy.

  49. Jennifer says...

    Other than Toby, this is the best week of outfits ever! Thanks!!

  50. Clay Terry says...

    Ashley, You so inspire me………you took your “too fat, too black, too poor” feelings & threw them in the dumpster of life regrets, where they will rot & die, while you FLOURISH! This 64 yr old, never pretty enough (a white gal who wanted straight blonde hair & a cute nose!) with homely legs & about 20 lbs over “ideal” weight………well, I’m tearing about 50 pages outta your life lesson book & I’m gonna have good times with what I have in the time that remains to me. Goooooo, Ashley & look out, New York!

  51. margie says...

    she is amazing, and I love her confidence. I wish I had that confidence.

  52. That swim suit is fantastic! So gorgeous. Love this article and Ashley’s style ?

  53. Vanessa says...

    Love her!

    And Cup of Jo ladies, keep doin’ what you’re doin’.

    xx

  54. Katherine H. says...

    This quote is so inspiring: “Now that I’ve stopped trying to control everything, I’ve ended up living a life where I get to feel excited, almost all of the time.” Words to live by! This is an important insight for so many of us. Thanks for sharing your words and style, Ashley!

  55. Adrien says...

    Ashley!! <3 I have been following her writing and interviews on various podcasts — what a great perspective she has! This is a great feature – she looks fabulous! Have an amazing time in Italy Ashley! :)

  56. Chiara says...

    Thumbs up!

  57. Oh I LOVE her! Her essay about her boyfriend and her body was one of my faves.
    I think her style, which is great, feels the most wearable of all the style weeks you’ve ever done.

  58. Aya says...

    I spent this whole article smiling and nodding and silently shouting “I love her! GO you!” Especially: not wanting to looker smaller or bigger just good, your grandma, not getting washed out, your smile, the yellow dress. I’m excited for you to go to Italy, have an amazing time and rock that bikini!

  59. “I don’t want to wear something that makes me look smaller or bigger; I just want to wear something that looks good.”

    What a beautiful mindset and amazing line! Seriously inspiring! I LOVE that grey dress with pockets! You are totally rocking it! And the picnic basket thing? Oh no! That would be awful!!!

  60. Y E Martin says...

    Amazing!! Thanks for the share!

  61. Megan says...

    “so I tried to do the big flower pin like Carrie did. I was like, I want to be a writer, ‘this is the way to do that, right?'” LOL! I have made this association with too many things.

  62. gina says...

    I devoured this up! Love the style, unique perspective and that this woman is not shy to be who she really is. Iam taking this to heart and wearing something bold tomorrow.

  63. Ashley S. says...

    Love everything about this! Not too fussy, too expensive, or too “much.” Just right! :)

  64. Amy says...

    Bravo, lovely lady. I’m a fellow Brooklynite.

  65. Quinn says...

    Yes, Ashley! That bikini is as hot as you are. You’re gonna rock that thing!

  66. Annie says...

    Gorgeous!

  67. Allison Luzader says...

    LOVE this. Such an awesome post.

  68. Claire says...

    You look terrific, and love these easy to wear clothes. All the outfits are so pretty. Love the way you use color too.
    But my absolute favorite thing is your grandmother’s flower earrings, and the story you tell about her being your best friend, and that you wear them when you want to feel her with you. That is so awesome. I never knew my grandmothers- they were gone way before I arrived- so that story really touched my heart.

  69. ceciel says...

    Ashley is beautiful and her advice on living life is speaking to me! Also–tons of comments on this post. Keep giving us women of color with all kinds of body shapes and attitudes.

  70. Diana says...

    Thank you for the inspiration!! Ashley is on point.

  71. Isabelle says...

    I feel like this was one of the first “week of outfits” feature where I really related to the clothes and could see myself wearing them (to be fair I haven’t read them all, but I find some I’ve read the women wear things that I think the average person might find difficult to pull off! Clearly style is objective). I also love her attitude. Amazing. Thanks for featuring her!

  72. Robin says...

    Hooray! So happy to see more of Ashley. I love the yellow dress and that swimsuit is crazy fabulous. Have a wonderful vacation!

  73. Jamie says...

    This is wonderful. I know exactly what she means about feeling like yourself. It such a brilliant feeing to stop worrying and just be who you are.

  74. Amy says...

    I love Ashley’s style! She looks amazing in that yellow dress- that outfit would make any cloudy day better. I am a sucker for color, fun earrings and classic, but comfortable clothes. I can really only afford the Target/Old Navy and Gap sale of the world, but there’s no reason that can’t be just as fun and fashionable as higher priced brands- especially with great jewelry and a fun lip! Ashley is a true testament to that.

  75. Chelsea says...

    Girl, you are me (or I am you). THIS is the way to do life. It has been so freeing and joyful to get older and genuinely let go of the worry, self-criticism, and doubt and prioritize things that matter. I always judge people’s maturity by how much they DGAF !!!

    • Beth says...

      Yes to all this.

  76. DENISE says...

    BRAVO! Ashley, you are beautiful!

  77. Lizzie says...

    So gorgeous!

  78. Jenni says...

    I love her style. Also I follow her and she has the correct look on life. I love universal standard they have a great fit and fits my minimalist style. I am glad to see someone up here that shares my love for the same clothing stores that I do. It’s hard at times to dress over a certain size. Mainly because people think we should not look nice. We have to love us before we can love others and live life. No one can do that for us.

  79. Elizabeth says...

    You are adorable! And you look so confident and stylish and happy.

  80. Love love love her outlook on everything. That yellow dress looks amazing on her, and LOL about the basket purse. I’m currently rewatching Sex and the City again from the beginning AND going to Italy this year too. :)

    Also checked out that ruffle top/denim bottom bikini – SO GOOD.

  81. Gorgeous! She pulls off that yellow dress like it’s nothing! Fabulous! Love that bikini too :)

  82. Maureen says...

    Love this post, it makes me feel better about my body! Ashley you are beautiful. Have a wonderful time in Italy together! :D

  83. kim says...

    great style

  84. L. says...

    She’s so BEAUTIFUL and FABULOUS!!!!

  85. Andrea says...

    Her outfits are so simple, professional and put together. But what I love most is her smile. It completes every look. Thanks for your inspiration. :))

    • Gen says...

      So true! What a smile!! Have a wonderful time in Italy :-)

  86. Maria says...

    Ashley, you are amazing! I feel so warm and happy after reading this, you just seem to exude positive energy. Thank you so much for sharing, and enjoy ROCKING that bikini in Italy!

  87. Love this! “Dorothy-on-her-way-to-Oz situation”
    “Being black, nothing washes me out.”
    So many good quotes! I want to be your friend!
    PS: The super athletic look is my fave!

  88. Janan E-W says...

    Love love love this style post! Can’t wait to read some of her work and keep following along.

  89. katelyn says...

    lovelovelove ashley! she is my favorite tweeter and i’ve had to give it up post-election. i’ve missed her. thank you, cup of jo!

  90. So awesome to see Ashely’s style on here!

  91. Lori says...

    Thank you for this! Ashley is absolutely stunning with great style and shops at places I can relate to. This is my fave so far!

  92. Jess. says...

    Ashley is such a writing goddess; I just adore and admire her. I was so happy to read anything more about her, and I love to see her style featured here. That yellow dress is a dream. XOX

  93. Juliette says...

    I loved this! She is reliable in so many ways (she shops at the Gap! At Target!) and her philosophy is so empowering. Thank you for fituring her on Cup of Jo!

  94. Joy says...

    I love her style, and I LOVE that she is smiling in every single one of these photos! I really enjoyed reading about her path to owning her style, too.

  95. Lauren says...

    This has become my new favorite series. Ashley, thank you for sharing your wisdom and style with us. It’s truly refreshing and inspiring!

  96. dy.nyc says...

    love this post!! thank you for featuring an awesome, gorgeous woman of color. more of this, please.

  97. Stephanie says...

    I never comment! But I just want to say how much I respect and admire Ashley and her honesty and outlook on life. This is a person I’d love to have as a friend.

  98. Nian says...

    This feature made me walk to my wardrobe, pick a dress that I haven’t worn in years (to much baby kilos left, muscles not toned yet, not sun kissed enough, blabediblah…) and pack it for the weekend getaway! What a positive energy this lady can create! <3

    • Beth says...

      Wow, great article! As a library worker, I want to say thanks for her support of libraries, too!