Style

A Week of Outfits: Gay Cioffi

Week of Outfits: Gay Cioffi

This year, early childhood educator Gay Cioffi, 66, is retiring from the preschool she has run for the past 38 years in Washington, D.C. “Kids have become my world,” she says. “My style depends on practicality and being able to move, but I still love dressing up.” Here, Gay shows us five outfits she wore in a week…

Week of Outfits: Gay Cioffi

Blouse: Theory. Pants: Theory. Shoes: Nisolo. Watch: Swatch. Fedora: similar. Sunglasses: similar.

“There’s no question that spending my life with children — doing art and music, getting on the floor with them, and dancing — has informed my look. For more than 30 years, I’ve worn a uniform of jeans or leggings with tunics or button-downs, and I tend to wear solid colors so I can throw anything together. And I really love OxiClean. There have been so many times when kids have run up to me and gotten paint all over my clothes.”

Week of Outfits: Gay Cioffi

Dress: Porto, similar. Shoes: Robert Clergerie, similar. Clutch: similar.

“When I was in my twenties, I spent a summer working in New York, and I fell in love with a guy named Mark. When fall came around, we went our separate ways, eventually marrying other people. Decades later, we both found ourselves single again. We became friends on Facebook and the rest is history. Now we’re married. Mark still lives in New York, so we see each other on weekends. Because I’m casual at work, this is my time to wear what I call my ‘weekend clothes.’ When we have friends over for dinner, I will put on jewelry, lipstick and heels — I’m okay with being the most dressed up person at the party.”

Week of Outfits: Gay Cioffi

“Because my clothing tends to be simple, I like to add fun accessories. I always, always wear bracelets and a watch. Ten years ago, my friend mailed me this soda tab clutch because she thought I would like it. Every time I go out with it, someone will say, ‘Oh, I love your bag,’ and then get closer and realize it’s made of soda tabs! It’s a good conversation starter.”

Week of Outfits: Gay Cioffi

Dress: Steven Alan, similar. Jeans: Gap. Loafers: M. Gemi. Purse: Cole Haan.

“I bought this yellow bag from Cole Haan and used it so much that I bought the exact same one in black. The bag is expensive, but I’m okay with spending my money on durable pieces I know I’ll use constantly. I like to do my shopping like I do my cooking — you keep all the basic ingredients in your kitchen forever and then you add some gourmet things every once in a while.”

Week of Outfits: Gay Cioffi

Jacket: Everlane. Blouse: Hope, similar. Pants: Hope. Boots: Nine West, similar.

“Right now I love the stores Porto, Steven Alan and Theory. A lot of my friends shop for pleasure but I don’t. When I find stores that I like, I’ll shop there over and over. I have a closet full of black dresses, and I also love red shoes! They’re a little surprise. Red clothing doesn’t look good with my skin tone, but it doesn’t matter with shoes.”

Week of Outfits: Gay Cioffi

Jumpsuit: Vince, similar. Shoes: Gentle Souls, similar.

“A couple of years ago, we were having a school dance with all the kids. The theme was School of Rock, where people were supposed to come dressed as rock stars. So, I had this idea that a black jumpsuit and a wig would be perfect. Although the jumpsuit started as a costume, I now wear it to parties, out to dinner and sometimes to meetings. I can dress it up or dress it down — it’s incredibly versatile. With maturity, I grew to understand what complements my body. There are lots of things that are hard about getting older, but that’s one of the good things: you really know yourself.”

Thank you so much, Gay!

P.S. More women share their week of outfits.

(Photos by Kate Headley for Cup of Jo.)

  1. I love this woman! One of my fav of this series. Actually, it’s my favorite to date….Her advice is practical, witty and GOOD! I also loved the piece on her third marriage and how they didn’t let it being the third mean they couldn’t make it magical, huge and worthy of that first wedding glory. Third time’s a charm. =)

  2. Harriet says...

    This has got to be one of the best features I’ve read on the blog. I love Gay’s personal style, which is not only chic but classic. Most of all, I loved the NYT article on how she reconnected with Mark, proof that you can find love at any age. So sweet!

  3. Chelsea says...

    Love her! My moms name is Gay, it’s pretty unusual but I’ve always thought it was chic. Her style reminds me of my mom too.

  4. Sheri Hamilton says...

    Love that you showed a woman of mature style!

  5. Shannon says...

    LOVe her

  6. Tracey says...

    I want to be like her! So stylish and chic.

  7. Janeen says...

    She seems so fun!!! :)

  8. Love it! She is so inspirational and a beauty too!

  9. Kristyn says...

    Talk about #goals! She is so incredible and reading her love story on NYT just brought tears to my eyes. Thanks for always finding the most inspiring women to feature!

  10. Oh my gosh, this post was so refreshing and lovely. Gay’s style is exactly what I’m aiming for as I grow older. She just looks so radiant and unique and relaxed. Thank you!

  11. What a BABE! Love these posts and that they include women from all walks of life.

  12. Jenn says...

    Hip hip hooray!!!! A style post about an older woman. It has been a long wait for well worth it. Keep them coming. Woman come in all sizes, shapes, colours, & AGES.

  13. Kristen says...

    Yay for the teacher feature!! We’re not wearing embroidered denim jumpers! :) I loved this post as a fellow educator and because I love that you’re sharing fab style in a big range of life seasons. She looks amazing! I’m on the hunt for those black platform wedges…

  14. caitlin says...

    This is just awesome. Bravo to CoJ and thank you to Gay for sharing her style.

  15. Dale Smith says...

    Thank-you so much for including a post about an older woman! We often feel invisible:)

  16. Karina says...

    Thank you for showing some age diversity! Even though I am only 29, I love looking at *older* women rocking it in the world & kicking ass. It’s inspirational. Life doesn’t stop at 35.

    • beks says...

      35 is hardly an *older* women ;)

  17. Samantha Zimmerman says...

    I want to be her when I grow up!

  18. Stacey Lee says...

    Style goals! Love this woman… and proves you can look super stylish at any age.

  19. Wendy Plump says...

    I love that you have included an older woman in your column, Jo. We are out here and we do read you and we are happy to be a part of it all!

    • Eliza says...

      Yes! As an about-to-turn 49 year old, I’m always looking for stylish older women to help envision what the future could be. Gay is an amazing inspiration (and a foil to the traditional concept of what a preschool educator looks like)!

  20. Patricia C. says...

    What an inspiring post! I love Gay’s style. So simple and practical, yet stylish and memorable. Love it!

  21. Lauren Roche says...

    Thank you for showing us Gay’s style. Although I am 30 myself, I think it’s so important to be exposed to women of all ages so ageing can be normalised and even looked forward to! I work with adults over 65 and my passion is building belief that we are worthwhile at ANY age.

  22. Y E says...

    RAVISHING!!

  23. Angela Bedell says...

    My favorite “Week of Outfits!” Love her, that she is a working, real woman and so stylish.

  24. Ahhhhh what a breath of fresh air this post was. I love seeing people age well. She’s stunning.

  25. Sasha says...

    Another vote for Gay for next president. (I’m so serious, a preschool teacher would know how to handle that job!!)
    Thank you for the inspiration, as a 44 year young nanny, these are outfits I can really relate to.

    I’m just throwing this out there, but I don’t see her look as “age appropriate” or “mature”….I think she’s got classic good taste and knows well what looks fantastic on her figure. She reminds me of Katharine Hepburn, or Audrey Hepburn, someone who feels comfortable with who she is, and it shows. Thanks for the awesome post!! And thanks for taking care of children Gay!

    • I agree! I’m 30 and would wear most everything in this post. Her looks is timeless and ageless. Beautiful!

  26. Angela says...

    I AM IN LOVE WITH HER AND HER STYLE!!!!
    Thank you – thank you for this series. Thank you for sharing something that made me happy. Your style is chic and you are amazing!!!

  27. Beth says...

    YAY for cup of jo embracing/reflecting career diversity (as well as age diversity)! As a teacher of small children myself it can sometimes be depressing to see gorgeous clothes talked about as “workwear” when I could never wear them to work in a million years! Love Gay’s style and totally relate to dressing up smart outside of work when everyone else is dressed down :)

  28. Meredith says...

    Love this post! Great style!

  29. Jojo says...

    I love, love, love her style; but I’m simply in love with how she and Mark reconnected and rekindled their love after all these years. What a great story!

  30. Cindy says...

    Standing ovation to the lovely Gay and to Cup of Jo! Love this.

  31. Mollie says...

    I love love love this series so much–especially the amount of diversity. It’s such a fun way to talk about clothes and fashion without feeling superficial. Perfect.

  32. sc says...

    Oh my gosh, LOVE THIS. Can totally see myself in each of these outfits!!

  33. Christy says...

    What a beauty!! This is so inspiring. We are not dead and unfashionable after 40.

  34. Annie Green says...

    Love this.

  35. Allison R says...

    I’m 39 now, but have been dressing like this (on a good day and when I can find the right pieces) for over a decade. Her stylish and pragmatic preferences speak to me for sure. I often feel like I am out of the loop because I think some modern trends look crazy. Gay gives me hope that I am not just stuck in a rut…she just knows what she likes and looks great. Cheers Gay.

  36. Dorca says...

    She is so beautiful!

  37. Michelle says...

    There’s something magical about seeing a person who is truly herself. The NY Times story made me tear up!

  38. Très chic.

  39. NKM says...

    This was SUCH a great read! What a lady! What a story! And her style – gorg!

  40. Super stylish!!!

  41. I love this! She looks so comfortable and content. Also love the story about Mark, and the article link *swoon*

  42. Floppo says...

    This woman story is amazing! I simply love her style too

  43. Nicole says...

    I love this. I’ve been reading the blog for years and this is perhaps one of my favourite posts. It is so refreshing to see an older woman featured. Gay is beautiful, chic, wise, and certainly a role model for young women like myself to look up to. Society needs more of this :) Now I just hope that I age as gracefully as Gay has!

  44. Allyson says...

    My favorite post of this series ever!!! Gay – can I be your friend??

    • Gay Cioffi says...

      Dear Allyson,
      Thank you so much for your kind words. They definitely made me smile!
      Gay

  45. Kristi T says...

    Thanks for this! I’m a believer that as we age, we just get better and better. We know who we are and care less about what others will say about it. Say it proud!

  46. I love this! She has some great poses!

  47. ewlake says...

    LOVE!!!

  48. Lynn says...

    Ok, you have become my style guru! I’m about to turn 57, I’m petite, look younger, and I refuse to dress like a matronly woman! I love fashion, I love this lady’s style! Just because you are over 50 or 60 or older does not mean you have to be frumpy!

  49. SCG says...

    While this pretty much sums up how I dress everyday, I want to be like her when I get to be 66!

  50. Too many women become invisible as they age – they wear dumpy clothes and don’t take care of themselves.
    Gay is the perfect example of a gorgeous woman that is celebrating her self, her age and her spirit!
    Brava!!!! keep posting about women of a certain age – we need to keep thriving and not disappear!

  51. Beth says...

    Smokin’ hot. Practically broken the internet. You get ’em girrrrll… SNAP

  52. jennifer says...

    So good! I loved this profile. I’ve been reading a lot lately about the importance of inter-generational relationships and how segregated our society is based on age… A lot is lost all around. In our youth obsessed culture, it’s so important to see and hear from women (and men) from all stages of life. This woman is an inspiration to this 41 year-old woman still trying to figure out what this new decade means for me on all levels including my style. Well done ladies!

    Jennifer
    Austin, Texas

    • Right, Jennifer. I’m 44 and feel invisible half the time and I take care of myself. I love Gay’s style. I’m all about practical.

      I’m in Austin, too!

  53. barb says...

    git it mama!….this is how you dress…luv it

  54. Cool woman with great tips I can make my own. Also, thanks Cup of Jo for coming to DC now and again. I like to see my hometown and her people and style highlighted.

  55. Jennifer says...

    Wow. Love, love, love this. She’s so chic, and the shoes! I’m in my 30’s, and I can’t get enough of role models for the decades ahead, examples of ageing gracefully and with style. Every one of these outfits makes me want to go shopping, and I hate shopping.

    Also, it’s so great to be seeing more and more women on here with more regular jobs; social workers, teachers etc. All the more typically creatives are fantastic too obviously, but it can give a sense that you have to be an artist to pull off a beautiful home or outfit.

  56. Katie says...

    Omgggggggah, this is exactly who I want to be for now and always. Her style! That hair! Also, her romantic life IS a Nora Ephron movie.

  57. Ali says...

    Gosh she is divine! Love her style

  58. WHAT A DISH. Add her to my list of women I want to be when I grow up! (Helen Mirren, Elizabeth Taylor, I know there’s more but it’s early and I can’t think haha)

    • Claire says...

      Nice list!

  59. Thao says...

    Gay’s uniform is brilliant! As a relatively new mother, I feel the need for a uniform too and hers is a perfect mix of stylish and practical. Love her devotion to the kids she watches and her excitement for life, which shows so clearly in her style!

  60. Alison Briggs says...

    love this post and love Gay!! So happy you included someone holder than their 30’s and how chic she is! And I am obsessed with her and and her husband’s story! thanks for sharing!!

  61. Wendy says...

    I loved seeing a post in this series about a mature woman. She is inspiring. And she is affirming my decision to be the only one of my peers (early 40s) going gray naturally. I get a lot of, “Why?!? Don’t do it! You are too pretty to go gray! – what does that even mean? I would also love to see a “Beauty Uniform” about her. I want to learn how to be so radiant at 66 – other than being in love and happy!

    • Lynn says...

      Yes! A beauty uniform!!

    • Sasha says...

      I’m there too Wendy! I colored for a long time but stopped at 42 (44 now). Going out on a limb, but I think my silver is really pretty :) And it’s so much easier and low (No) maintenance. It’s so freeing to stop following beauty norms. I feel more like myself than ever.

  62. Sara says...

    Oh lord I’m crying after reading the Times piece about their wedding. What a beautiful soul you have, Gay. What a beautiful life.

  63. Niamh says...

    What a super babe. Love her style! Love this series!

  64. Cláudia says...

    oh her love story…. so beautiful!

  65. Carol says...

    This is exactly why I have never got bored of this Blog, its always so interesting with diverse topics and pieces for all age groups. Definitely my favorite ‘Week of outfits’ so far. Gay radiants happiness and her style is something we can all aspire too, age appropriate yet not dowdy with alot of sparkle…..wonderful!

  66. Jess says...

    Could NOT love this more. Ladies like Gay make me excited to get older. Love love love.

  67. Ewa says...

    Fantastic style! Really suits her personality. Love that you feature such different women in a “Week of Outfits”

  68. Mathilda says...

    Thank you so much for this great post. Totally loved it!

  69. laura hobbs says...

    Wow she looks fabulous. Would love to look that good when I am that age.

  70. sharon says...

    How refreshing to see an older woman on COJ, I’m 56 myself. Can we see more of them please? I’m a daily reader, after doing my morning prep at work, when I have a quiet 10 minutes, your blog is my go to for up to date news and trends.

  71. TB says...

    49 yr old mum of three, long term COJ reader here – delighted to see a bit of age diversity and what fab outfits

  72. Candice says...

    You look FANTASTIC!

  73. Kristin says...

    Absolutely lovely. Someone like Gay reminds us women in our 30s that the best years are to come! Thank you for stepping out of the fashion blog box.

  74. Emily says...

    She is so lovely!

  75. Sue says...

    Thank you for posting Gay’s outfits. I am 56 (my daughter, 32, suggested I read your blog, and now I am a devoted reader!). It is difficult to know how to dress at 56. I love all the clothes my daughter wears, and I can fit into them, but just because I can, does that mean I should? Gay presents youthful looking outfits that look appropriate for all women – 32, 56, or 66 years old.

  76. Ally says...

    Fab! Congratulations on a great and constructive career. ??

  77. Kathy says...

    Yippee! I’m a 61 year old woman who appreciates this feature of a 66 year old woman! Hope you’ll do more features like this one with women of varied ages.

  78. Sandra says...

    I’m almost 50 and I love seeing a someone featured who is older than your usual “Week of Outfit” subjects. And I love her sense of style–just beautiful!

    However, I have a 7 year old and never in a bazillion years would I wear a $275 white shirt around children, no matter how much Oxiclean I had on hand.

  79. Ramya says...

    Hi from another DC teacher! Thank you for all you do and for looking amazing while doing it.

  80. chika says...

    Oh my, her love story made me cry…and goodness gracious, could Gay be any more lovely and chic?! Wonderful choice of a woman to highlight– well done, COJ!!

  81. Karin says...

    Thank you so much for featuring an older woman! I’m 55 and love your blog. I also LOVE this woman’s style. (Actually it’s a lot like mine). I can totally relate to being the only one who dresses up for night since I also have a casual job. Love to bring out my bling!

    Would love to see (a few more) older women. I realize it’s not your target demo but it’s nice to mix it up!

  82. becs says...

    Oh wow, this lovely lady is my cup of tea! I, too, love solid colors, button downs, and red shoes. In fact, I wore chambray button down shirts as a young high schooler and couldn’t wait until I was an adult so I would finally look my age. Ha!

  83. Ashley S. says...

    Simple, chic, love it. Especially love that she was a teacher and that her style reflects function!

  84. Sarah says...

    This might be my absolute favorite post since I began reading this awesome blog in 2008/2009. I am 39 years old and am always searching for role model women who grow older with grace and beauty. Gay is the epitome of that … that NY Times link about her love story, too…SWOON. :) Thanks for the great post!

  85. Katie H. says...

    I want to be her! What an inspiration…

  86. Absolutely gorgeous. Stylish & real. x

  87. Karen says...

    As a 57-year-old preschool teacher, I am totally inspired. Thank you for sharing Gay and her beautiful style with us.

  88. emily says...

    i’m a NW DC mom and totally recognized gay – my bus to work passes her school every day!! i’ve seen her and the other teachers greeting students. thank you for another glimpse into the life of a lovely, happy, real woman.

  89. Amelia says...

    <3 <3 <3 <3 <3

  90. Sadie says...

    Loved this story! More older wise and stylish ladies please!!

  91. bisbee says...

    Love this! It’s wonderful to see this woman on your blog…totally stylish. And…she’s the same age as me! I’m retiring this year too!

  92. Dawn says...

    Gay is the coolest and most chic lady! She slays in every photo…What great inspiration for us all (at any age!).

  93. Emily says...

    What a lady! Another fellow teacher here, and love seeing inspirations like Gay! She looks approachable, friendly, intelligent, and cute. Keep up the great work!

  94. Jen says...

    I don’t comment either (but always read). I loved this piece! Gay is gorgeous and her style shows her personality. I really enjoyed her perspective and the beautiful pictures. Thank you!

  95. Another elementary teacher here (well, SAHM officially starting this month, since student are heading back to school this month and I’m staying with our six month old son!) and so thrilled to see a teacher shown on this series. So empathizing with her talking about needing to be able to move in her clothes etc. Gay has a truly wonderful style and her own flair- I see other teachers dressed in this way (but with their own twists to things), so it feels very representative.

    The red shoes especially delighted me. Red shoes are my favorite too- they make me feel like Dorothy in Oz!

  96. Julia says...

    What a great style, she is gorgeous! I’m 25 and feel so inspired :) love the jumpsuit especially.

  97. Kate says...

    My favorite yet.

  98. kaela says...

    Gay, you are incredible. I admire your simple laid back style and charm. It is so telling that you were satisfied and grateful for the loves you were already given… and yet you let love in again. Such a sweet life. Thanks for sharing! xo

  99. Annie says...

    PURE GODDESS. She just radiates a bright energy in all her photos. I want to dress like her and I’m not even 30 yet!

  100. Jenny Mothoneos says...

    How super to see a piece about an age group of women that is often forgotten when it comes to fashion

    • S. Morris says...

      I agree, thanks for featuring this beautiful lady!

    • Suzy Quinn says...

      I agree!!!

  101. What a babe !
    The way she wore that layered necklace under the black blouse is so damn chic. I am going to copy that outfit.

    Thank you for featuring her.
    You guys create excellent content. It amazes me that every single post is as good !

  102. Jill says...

    Thank you so much Gay! I am a preschool teacher as well, for about 15 years, in Los Angeles. No one can understand that this job is THE hardest to dress for!!!! You do much better than I – I live in my uniform of jeans and tees with kid friendly characters or kid friendly words or cute cartoon pics, ballet flats or converse. But seriously, it is soooo hard to find jeans that are cute yet don’t show too much when you bend over!!!! You look great and thank you for your years of service to the WORLDS MOST IMPORTANT PROFESSION!!!!! Those little ones definitely keep you young, you look amazing, happy and joyful. I have been asked to work as a parent specialist bc I have a Masters Degree and I miss those little ones so much. I think I should rethink what I am doing, I want your skin, hair smile everything!!!! Good luck in the future and don’t ever stop asking people if they need to go to the “potty”. I don’t think I will ever be able to shake that habit!

    • Sasha says...

      I love your comment Jill! I’m a nanny and I can relate to so much of what you said. My husband doesn’t even bat an eye if I ask him “need to potty? Got your water? Snacks?” as we head out the door ;)

      Have you tried Lola jeans? My 20 yo found them for me and insisted I get a pair because they make me look “hot” lol. What makes them awesome is the waistband, it’s like yoga pants, but they are way more jeans than jeggings. So you can bend over, sit on floor, etc, but no gap. And except for the waist, they just look like cute jeans. Those, plus comfy dresses or tunics or sweaters over leggings are my uniform. And crocs for in house, closed back clogs for outside – have to be able to run!!

    • Jill says...

      Thanks Sasha! I just bought some J Brand high waisted crop jeans. So happy they are making high waisted again, no more preschool/ plumbers butt! And everyone loves that I make my husband and 12 yr old go potty before we leave the house! Hahahaha!

  103. ALI says...

    Gay is such a baller!! I LOVE HER!

  104. Dana says...

    Definitely one of my favorite “Week of Outfits” post yet. Gay emanates the style I’d love to embody when I’m her age. (And I love that she is proving that there ARE hip, fashion-thinking women here in DC!) Thank you so much for featuring such a beautiful, graceful, funky woman.

  105. Claire says...

    Wonderful style, and a lovely and interesting woman. Love the blue shirt dress, and the red shoes.
    more women in the afternoon of life, please.
    and more love stories, please.

  106. Margaret says...

    I have to echo the others who have said what a lovely suprise it was to see an older woman profiled in this series. But after I started reading, my favorite thing was her style in front of the camera. She has such presence and vibrancy.

  107. Emily says...

    I love that you have done a profile of an older woman. I’m 25 myself, but really appreciate seeing all kinds of diversity and sometimes it seems that older people are barely seen in the media!

    Also it’s great to see an older woman looking chic (esp love the last all black outfit) and be hopeful I will look that good at her age.

  108. Julia E says...

    great style!

  109. I LOVE that you ladies are sharing a more diverse set of folks. I just sent this article to my mom, who has complained to me that fashion blogs are so rarely about older people (even though she, in my opinion, dresses quite well by the standards of someone of any age — as do so many of her friends). I love Gay’s outfits — especially that first one. Those sneakers with the tunic + leggings would work for anyone!

    • Britt says...

      If your mother hasn’t seen it, she might the blog Girls of a Certain Age, which is geared toward 40s+ women, but written by the founding editor of Lucky Magazine, who knows fashion. I’m in my 30s and I love it, but I get the feeling most readers are 40s, 50s, 60s. Apologies if this is old news!

    • Karin says...

      Your mom may also like Une Femme D’Une Certaine Age – she’s a 60 something blogger with style a bit similar to this one, modern/hip.

    • Robyn says...

      Also tell her to look at That’s Not My Age-one of my favorites.

  110. I’m 34 but she is my entire aesthetic goals. I thought this was an Eileen Fisher ad at first. You are truly beautiful, Gay!

  111. Lucy says...

    Long time reader, first time commenter. Love this post so much – thanks for adding some age diversity to an already great series.

  112. Ally says...

    Loved this feature! What a stylish woman, and LOVED the back story of re-finding her summer love….magical!

  113. Emma says...

    Yes, this is so similar to my style, almost entirely professional, I love solids and tunic style. I am only 31 but love walking past trends I know won’t work for me, glad there is more of it to come.

  114. AJ says...

    LOVE this one! What a great spirit, great outlook, great style! And great love story to boot. Inspiring. And Gay is simply fantastic in front of the camera…

  115. Val says...

    One of my fav posts! And the NYT article about their romance made me cry! Thank you for sharing this lovely profile~

  116. Terry says...

    Such a treat! It’s obvious that Gay is fully in her life which is a goal for anyone at any time in their lives. Every life is different, but there are enjoyable moments in each phase, including moving on after a divorce and discovering more about yourself. I love reading blogs about women’s choices in different decades, and feel so lucky to work in a place with women from 20-65, and volunteers who are vibrant in their 70s! I would not want to be always around only people my same age. We have so much to learn from each other. So glad to see Cup of Jo embrace diversity in so many posts!

    Wonderful reminder of Nora Ephron. Would love to see her sister Delia make a movie of this romance!

  117. Loribeth says...

    This woman is killing it!!!

  118. Mari says...

    Favorite week of outfits yet. Beautiful.

  119. Always think being 61 maybe I’m a little too old to be reading Cup of Jo?! But of course I’m never going to stop visiting this amazing blog :)
    I just love this post and everything Gay has chosen to wear!! made my day :)

  120. Maria says...

    LOVE seeing a woman with grey-ish hair, over the age of 50, featured here. As many have already commented, it’s fantastic to see someone so beautiful and stylish in the “older” category celebrated. I’m 48 and in the past 2 years have chosen to let my hair go grey. It’s odd in many ways how many comments I receive about how “bold” it is for me to do so. Overall, it’s simply been liberating, and many, many people comment on how beautiful my hair color is so going grey might just be alright. ;)

  121. ” I like to do my shopping like I do my cooking — you keep all the basic ingredients in your kitchen forever and then you add some gourmet things every once in a while.” – is going to be my new motto!

  122. She gives me life!! Love minimalist outfit with funky accessories!

  123. Sarah K says...

    I’m 37 and I am so inspired by all these outfits–and by Gay’s whole demeanor. What a beautiful, confident example! Love everything about this.

    • Right? Everything is perfect.

  124. Love this!!! She has great style.

  125. Emma says...

    Best one yet. I want to be this woman, now and in the future.

  126. Lori says...

    This is ridiculously glorious . LOVE her story and her style.
    Just. The. Best.

  127. Jean ann says...

    I’m probably older than Gay but really appreciated this! Thank you!!

  128. As a 68 year-old children’s book author who has let her hair turn completely gray, I really appreciated Gay’s style. My daughter @saga.nordisk sent your blog post to me, perhaps because I’m a fan of white shirts. Great photos!

  129. What a babe!

    Thank you so much for posting such a wide array of women all over the spectrum in these ‘week of outfits’ and beauty uniform posts. I’m 30, and it’s SO inspiring to see what women older, younger and my age are doing to care for themselves each day and represent themselves. <3

  130. Annie says...

    Inspirational! I am 58, more more more of this please.

  131. Lenae C says...

    Thank you so much for linking the accompanying article about their love story! It’s so sweet. It’s like a Nora Ephron story in itself – their back-and-forth Facebook messages remind me of “You’ve Got Mail.”

  132. Nicole says...

    How fabulous is she!! As a teacher, this post was somewhat inspirational. I definitely need/look for pieces that will allow me to move around (I walk around 16,000 steps every day!) but I also always want to look nice for my job. In some ways, fashion allows me to connect with my students, plus they’re so honest, I get to find out what works or doesn’t work for me :)

    Ps. Today was our first day of school and I was so anxious to meet the kids, I totally dressed up!

    • Mindi says...

      I always have a “first day of school” outfit! It helps start the year off on a positive note, I think. I hope your school year is fantastic, Nicole!

  133. Lindsay says...

    Love this post!! Gay is my style spirit animal. I appreciate you guys posting women of all ages, body types, etc.

  134. molly says...

    …And their love story!!! So. Sweet. :)

    • I just read it and now someone is chopping onions at my desk, weird.

  135. Jo Henthorne says...

    What a fabulous, wise, fun woman! my favorite week-of-outfit post yet!

  136. whitney says...

    I have NEVER commented before and have read every day for 9 years. This is the best! I’m 30 and I’ve been looking for older women in the world to look to, and this is it! She is classy, has held a real job that contributes to the world and looks SO fly while doing it. I am so happy about this post.

    • Cynthia says...

      She does look so fly! Gay is serving it

    • Sue says...

      Ditto to Whitney. I have NEVER commented either but feel compelled to in this case. What a beautiful, confident, accomplished woman who’s not only a model for younger women (i.e. Whitney), but also for women my age, 54+ — someone we can look to for inspiration and validation. Thanks, Jo. Nice to see all ages/types/nationalities/styles represented on your blog and to feel included.

    • kaela says...

      Yes! This! Love Gay!

    • Meg says...

      I’m with Whitney! This is what I want to see: someone who has class, style, humour, interesting stories to tell, and experience doing worthwhile work in the world. This is what women need! It’s like a life road-map of sorts. I don’t know exactly how to get there, but this is where I want to be: sure of myself, happy with my contribution, stylish and full-up with my life! Saving this for future outfit ideas, too.