Style

A Week of Outfits: Piper Gray

A Week of Outfits: Piper Gray

Piper Gray, a copywriter at Warby Parker, lives on the Upper East Side of Manhattan and has awesome style. “I think I have a magpie tendency,” she told us. “If it’s colorful or bright or shiny, I’m automatically intrigued.” Here, she shows us five fun outfits she wore in a week…

A Week of Outfits: Piper Gray

Denim halter dress: Gap. Scarf: travel souvenir. Sunglasses: Warby Parker. Tote: Loeffler Randall. Helmet: Bobbin. Shoes: Anthropologie.

“Every fall, I toy with the idea of getting a uniform. I think, maybe this is the year! But I know I’d get bored with that. Still, there are pieces that repeat frequently — like this denim wrap dress. It’s backless, so I cover up with a scarf at work.”

A Week of Outfits: Piper Gray

Shirt: COS. Skirt: Old Navy. Sandals: similar. Bag: ban.do. Sunglasses: Warby Parker.

“I wear a lot of bright colors, and I joke that the day that I start to wear all black is the day I should leave New York. I’m from the south, so I don’t have that urbane approach to dressing. I do love black-and-white graphic stuff, though, because it looks great mixed together. The skirt is from Old Navy, which, by the way, has been killing it recently. I was looking through their sale rack, and it was a $9 find. It has that Mad-Men-esque vibe to it. The silver bag is actually a lunchbox!”

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A Week of Outfits: Piper Gray

Shirt: similar. Pants: similar. Pink shoes: Nasty Gal. Backpack: Herschel, with a Pucci scarf. Sunglasses: Warby Parker.

“On my bike, I always feel like such a goober with my backpack and helmet on. Obviously, I’m all about safety, but it’s hard to feel that cool when you’re loaded up with everything. So, a gold helmet was one way to add my flair. I catch glimpses of my reflection passing by building windows, and I’m like, oh, yeah, that’s definitely vibrant. Since my backpack is super utilitarian, I tied on a Pucci scarf to dress it up. It was on sale at a boutique in Memphis, and I thought, this is my chance to get one.”

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Chambray blouse: similar. Black pants: Loft. Sunglasses: Warby Parker. Tassel earrings: Hart Hagerty. Tote: Loeffler Randall. Sneakers: similar.

“My running shoes are black and white polka dot. I hate hate hate the phrase ‘classic with a twist,’ but they are classic with a twist. Since I bike to work, I wear Nikes or ratty white Supergas with the grand hope of changing into nicer shoes when I get to the office. But, I have to admit, more often than not I end up leaving them on all day.”

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Dress: vintage DVF. Moto jacket: simliar. Bag: ban.do. Sandals: similar.

“After my grandmother died, we discovered a never-been-worn floor-length Diane Von Furstenberg dress from the 70s in her closet. The tags were still on. I’m the only grandchild in my family, so no one else was clamoring for it. I took it to a tailor and got it hemmed shorter. My college roommate used to call the print ‘TV static.’ It’s a special piece to me, and I like that it doesn’t feel frozen in time.”

Thank you so much, Piper! Your style is wonderful.

P.S. Five more outfits we’d love to copy, and a trick for making mornings easier.

(Photos by Ana Schechter for Cup of Jo.)

  1. Selina says...

    finally someone who isn’t scared of colour and pattern. I love her style. All black is not for me either. Love the helmet and lunchbox details, very creative

  2. Veronica says...

    Her gold helmet is amazing.
    If ya’ll want a US maker of great commuter helmets check out http://nutcasehelmets.com.

  3. Ann says...

    I love the Von Furstenburg dress story!!!

  4. Sarah says...

    I love this series!

    Piper, you have the best accessories. I’m on the hunt for some bright and cheery shoes and that Loeffler bag now!

  5. Anna says...

    Loved this post! Such fun style!

  6. lomagirl says...

    I love your style! Thanks for sharing with us. I’ve decided I should just wear sneakers to work- but I haven’t found the right pair to go with skirts and pants, yet.

  7. Ellen Weber says...

    I love this post! I’d love to see a series of posts like this, just like I loved the beauty uniform posts. <3

  8. Courtney says...

    I’ve been reading since very near the beginning. <3 have loved following along as a lot of our major life events have happened at the same time! We got married in the same month back in the day, my eldest daughter was born the same week as Toby, and our second daughter in the same month as Anton. So fun to see the parelells! Thanks for keeping such a fun, uplifting space here for the last decade!

  9. Jessica says...

    Awesome outfits Piper! Love the chambray polka dot backpack – especially since I carry the same exact one as my diaper bag :-)

  10. The story about her grandma’s dress? GOSH! That is beautiful. I love the TV static. :D

  11. Molly says...

    Piper is a goddamn style icon.

  12. escondista says...

    Go Piper!

  13. I have that top Gap dress and it’s been great for maternity wear! It’s adjustable so at 31 weeks I still have room. Love it since it’s backless, keeps me from feeling frumpy!

  14. Shoot, even her NAME is stylish: Piper Gray! So good it almost sounds made-up!

    I especially enjoyed seeing styles that can be worn to work in an office and include practical points like shoes that can be worn on the commute. Love this series – more please :)

  15. I am LOVING this series! It’s so fun to get a glimpse into real people’s wardrobes. I love her take on personal style and how she adds a little flair to every outfit.

    xo,
    Shawna || http://www.shawnaleeann.com

  16. Emily says...

    Gosh, she’s beautiful. And I LOVE that name!

  17. I do love your TV static dress. and I am part magpie too! Friends have said they know its me when they drive by on the street because I always have something bright or sparkly on. Makes the day go better feeling bright and sparkly! :)

  18. Jess says...

    Love this! So many great outfits I could wear at work and such reasonable brands. Thank you!

  19. Renee says...

    More of this series, please! Piper’s got serious style. I love that her outfits include high-end items but also things that are more affordable. I also like that she mentions practical things like a bike helmet and wearing comfortable shoes. Awesome post and very inspiring! This is truly style for REAL life!

  20. Suzanne says...

    I loved this post!!

    Piper has such great unique style that’s accessible. I often read posts like this and think “no way would I ever be able to wear that.” I read this one and thought, “I could TOTALLY incorporate this more into my style.”

    Thank you, Jo! And thank you, Piper! You are glowingly beautiful!!! :)

  21. OMG that gold helmet!

  22. Lauren says...

    Piper Gray! Get it girl! What a beauty, inside and out, and so in awe of your creativity. Love how you are inspiring so many people.

  23. Katie G says...

    My favorite fashion post on your site ever! So many times it’s hard for me to relate to fashion posts on blogs because either the outfits aren’t realistic for my life (I work in a fairly traditional office job) or all the clothes are from obscure brands that make everything from unicorn manes so a single shirt costs more than my monthly clothing budget. But Loft, Old Navy, and Gap I know where to find and I can afford. Thanks for featuring this one!

    • I 100% agree! These are the places I go to regularly when I shop for new clothes! Thanks for a great post, Joanna + team! XO

  24. Emily says...

    Love Piper and her style. Dying over her snazzy gold helmet! Thanks, Jo and team for featuring real life women with real life bodies and budgets. This blog and its comment section is the best place on the internet! xx

  25. Love this girl – and her personality and heart are as bright as her style! Thanks for featuring her delightful self!

  26. Abigail says...

    LOVE this! I love this feature, and I love that this round features someone who has great style, but seems unfussy and down to earth at the same time. Hats off to you, Piper (and of course the CupofJo team)!

  27. I love the stripy shirt outfit and super cute sunglasses. What a relief to see a gorgeous model that can give me an idea what I would actually look like in those clothes too. Thank you.

  28. Margaret says...

    Way to go, Piper!!!! Such a trend setter!! xo

  29. Lauren says...

    Absolutely love Piper’s style! So refreshing, unique, and vibrant.

  30. Maggie says...

    She looks like me!! Retailers never do this – thank you for doing it!!

  31. Lauren E. says...

    I need all. of. the. shoes.

    Love this!!!

    • Mary says...

      ERMERGAWD.
      Exactly.

  32. It’s always inspiring to see someone embrace style while cycling, and advocating for safety with a rad helmet. I love this lady.

  33. Her smile reminds me of Drew Barrymore!

  34. Clara says...

    Love her style! I want more of these types of posts! This is great!

  35. Emilie says...

    Piper is gorgeous and I love her colorful style! Also appreciate you featuring a woman with curves on the blog – she looks fab. Loved her story about her grandmother’s dress. Those are always the best pieces! I have a pair of Frye boots from the 70’s that I found in my mom’s attic, and they are still my favorite article of clothing :)

  36. Sonya says...

    Love Piper and love this new series! I definitely feel inspired when seeing a real, relatable woman with great style.

  37. Rebecca says...

    I loved this post about a woman with a normal body and a normal budget with great style and taste. More please!

  38. MariainMaine says...

    Piper has great style!!! This is my all time favorite fashion post from this site.

  39. shopgirl says...

    I am not very “magpie”, but for this fall I bought myself very yellow Moleskine tote bag! :-) Goes great with grey, black, dark blue or marine stripe look, all my favorites..

  40. Stef says...

    OMG i love her!
    I have a very similiar figure and i am thrilled to see a woman with curves in cool and feminine Outfits – i printed out every picture and taped it onto my closed doors. Such an inspiration!

  41. Kristin says...

    Love this! Hope it becomes a weekly feature with different women every week. x

  42. Emily says...

    I seriously love her style. It’s left me feeling inspired. Thanks Piper for sharing!

  43. Terrific post! Love Piper’s style…so much so, that it would be great to know who made the pieces she’s wearing, even when they are no longer available. I appreciate that you linked to similar items – but it’s fun to see what a designer/seller of previously awesome styles is up to for the current season too.

  44. Gem says...

    Such great style! I knew I was going to love this woman as soon as I saw that awesome gold helmet!

  45. How gorgeous. Such real style. I am in love with the gold helmet & the outfit with denim bow blouse & sneakers rock. Thanx for the inspiration. xxx

  46. Daynna says...

    She’s got loads of style and heaps of class! I love her look and her outfits and her everything, really, but also, I ADORE seeing someone who’s not model skinny, which is what we usually see everywhere. I mean, she’s clearly got a great body, don’t get me wrong. She’s thin with curves, which is the best. But she’s not the skinny, perfect hanger model body. Because only a few of us have that shape, very few.

    So thank you for featuring someone who, while still being thin and beautiful, has more of a normal, slightly curvy look that most of us can relate to. It would also be so amazing if you could feature a lot more people of color too!

  47. Jo says...

    Piper’s style is so cool! I love her quirky pieces and love of color and prints.

  48. Margaret says...

    More of this series please!!! What a great one to kick it off!

    • india says...

      there was one a few weeks back, its linked as a PS.

  49. Elizabeth says...

    Love this feature! Her shoes are magnificent.

  50. Meems says...

    PIPER, Please magically appear at my home and help me put together five amazing looks like yours. Girl, you got style, class and are humble to boot. Love!

  51. Kim L. says...

    Loveeee this post about a woman with a normal body and a normal budget, and doing simply fabulous things with both. Kudos Piper & CoJ!

  52. Emma says...

    Loved this post!

  53. Betsy says...

    Love her!! What a gorgeous, fabulous girl. And her commentary! Clearly her sense of humor is as amazing as her style. Can’t imagine a more perfect model to start off this series. Well done.

  54. She looks so effortlessly chic! I love the blue tasselled scarf in the main picture and those tasselled pink earrings paired with Nikes! The bomb!! More of this sassy dressing please =)

  55. Lindsay says...

    She’s wearing those clothes, they aren’t wearing her. What a confident and classic beauty you are Piper. Thanks for the feature.

  56. dee says...

    I love her looks. She is beautiful and thank you for posting some fashion that does not center around a waif like woman…

  57. Greta says...

    Piper is so inspirational! Thanks for featuring looks that mix high and low on such a beautiful woman!

  58. I’m obsessed with her style. From her clothes, to her shoes, to her AMAZING haircut, so cool!

  59. Candice says...

    Beautiful! I loved it!! I like that you are branching out a bit from your own style. I like to see posts from people with a mix of styles. Thanks!

  60. Liz says...

    I’m inspired to up my bike helmet game!

  61. ooooh fellow southerner! now i’m dying to know where in the south she’s from!?

    • I went to high school with Piper! We’re from Memphis.

  62. Beverly says...

    Love this post and Piper’s style. May I be your next curvey model? Thank you, Joanna.

  63. Kara says...

    Piper looks great!! Love this post and the whole series … what fun to see such a stylish awesome girl!

  64. Great colors on the first scarf! I love buying scarves when I travel.

  65. Carmen B says...

    I love all of these outfits.
    Girl’s got style!

  66. S says...

    Obsessed with that pink moto jacket!!!!!!

  67. So beautiful!!

  68. Michele says...

    I love the hot pink moto jacket over the vintage DVF! You’ve got style, Girl!

  69. Ellen says...

    I love this new feature! So inspiring and fun.

  70. Fiona says...

    This is awesome, I wish Piper would help me go through my closet and figure out how to make such charming and vibrant outfits – I have so many fun pieces, but never know how to put them together and not just look like a scraps bag at the second-hand store… Way to go Piper!

    • Melissa says...

      I so hear you on this, Fiona! Making outfits is hard. :/

  71. Kate says...

    I loved how relatable this feature was. Piper looks great wearing fun, affordable clothing. It’s fun to see someone who is chic but still playful.

  72. Genevieve says...

    Piper!!!!!! So fun to see you on here! Stylish ever since college :) Get it girl. Xoxo. And Joanna, way to go featuring such a vibrant person, both on and off screen.

  73. Karen T. says...

    Adorable! And the DVF dress–what a find! My grandma left us all furs…:(

  74. Jessica says...

    So nice to see color and that Southern charm come through! From one Southerner to another… I’ve definitely fallen into the blac-on-black category, but I always make sure I’ve got key pieces in bright colors to mix it up!

  75. Karen says...

    Loving the black and white… Would like to see outfit #2 with the pink moto jacket and pink heels! Need the pink and turquoise shoes too.

  76. kelly says...

    GORGEOUS! Thank you featuring a beautiful, stylish plus-sized woman here – I’ve been waiting and hoping for it! And omg – I love her name (totally sounds like a feisty book heroine). :)

    • Stephanie says...

      Is she really “plus-sized”? Hear you on being inclusive but 1.) I don’t think this qualifies as “plus” and 2.) we’ll never move forward if we don’t stop categorizing women’s shapes. Anyway – your comment was very sweet, I just felt like it had to be said. p.s. I love her name too :)

    • jen says...

      Same. She looks normal size to me, too. Love that gold helmet.

    • cgw says...

      ditto what stephanie said.
      i viewed her as normal… as in i didn’t even think about her body type until i started reading comments.

  77. Tracy says...

    Lovely style!!! I adore this series.

  78. Diana says...

    Okay…MAJOR shoe envy over here!

  79. Kim says...

    How fun! I like her creativity in finding items that work for her (using a lunchbox as a bag, dressing up her backpack with a scarf).

  80. Sandra says...

    Love this one! My wardrobe used to be all black, gray, and navy, and now that I am getting older it kind of washes me out. I never thought of just adding pops of color like she does! Also, I have the same denim wrap dress and don’t wear it a lot since it feels a little bare in the back for some occasions–I love how it looks with a colorful scarf! Thanks for the inspiration!

  81. jeannie says...

    I love this! She is so lovely. I especially like that Chambray shirt. And – wow! – all those shoes!

  82. KT says...

    Love her use of bright colors and mixed prints. Inspirational!

  83. liz says...

    Super adorable gal, super cute wardrobe, can I be so bold as to suggest she retire the denim dress? I think she looks 1000x better in the other outfits. When you are that fetching your clothes ought to make you shine.

    • Alice says...

      I respectfully disagree! That was my favorite look! So so cute.

  84. She is lovely. I am so charmed by her gold helmet and the reasoning behind it. And the DVF dress!!! What a great story. Piper, you’re awesome :)

  85. Tina, nyc says...

    Love all your looks Piper! That hot pink moto jacket over the DVF dress is so chic and fun. You have style in spades. Thanks for sharing all your looks! I’m going to mix some black and white prints in honor of you and your fab grandmother!

  86. meredith says...

    THAT MOTO JACKET WAS IT FOR ME. I love that color and think it is universally flattering.
    She is so cool.

  87. Dana says...

    I love this series! I would love to see someone featured who has more tomboy-ish style–I’m someone who veers a little more masculine in how I dress and could use some inspiration!

  88. Bethany says...

    I love how different this one was from the previous post in this series (which I also loved)–sometimes in the blog world, all of the “outfit posts” can have a similar feel and aesthetic. I also thought Piper’s outfits were outfits that I could put together myself and not crazily expensive. I love this series! And I love seeing what other women wear to work. It can depend so much on the environment/city you work in.

  89. Loved this post! So nice to see someone on your wardrobe posts that a similar body shape to mine. The first in a long time!
    I also love that she shops at Old Navy and Gap! Old Navy has definitely been killing it lately. Great style!

  90. Shannon says...

    Love her style. Thanks for sharing.

  91. shanze says...

    i’m never brave enough to wear prints- especially two- and they look so cute & alive – just had to say i love how she calls herself a goober! I want to be friends. Also love that a southern girl stayed southern in NYC :-)

  92. Jen says...

    Enjoyed this very much! Especially like that she is a beauty but not stick thin. Many of the beauties on cup of jo are very thin!

    • Agreed! Really nice to see.

    • Beth says...

      I loved that in the article how there was no *but* about her size–a la, she’s not stick thin *but* she can still be fashionable. Does this even need to be said? Can we refrain from talking about her size in the comments? Even if it’s a positive-ish comment it perpetuates cycle of commenting on women’s bodies and apologizing for non-super skinny ones.

    • Val says...

      I think the comments on size are less directed at the featured person, and more as positive reinforcement to the Cup of Jo team for finally starting to feature a diversity of body types, sizes, and complexions as examples of beauty. There are so few blogs that do this, including this one for a long time, and if the readership doesn’t voice their desire to see more than just one type of women, I don’t see change happening. Joanna, the effort has not gone unnoticed, and all I can say is MORE MORE MORE!

  93. Sara M in Boston says...

    What a treat. Loved every outfit and her smile.

  94. Ah lovely pops of colours everywhere! Wishing that I’m game enough to incorporate them in my outfits…!

  95. Amy says...

    Looove the first and last outfits! Piper is beautiful.

  96. Xavier says...

    She has a beautiful, warm smile and her Grandmother must have been one stylish lady!

  97. Meg says...

    This is a great feature! Love this.

  98. Patti says...

    LOVE the vintage DVF that she made her own. What a great piece to remember her grandmother by! Super stylish!!!

  99. Alice says...

    What a beauty! Love her smile and now suddenly want turquoise shoes.