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Could you wear one print, style or color for five days in a row—in five different ways? That’s the challenge we’ve been giving to a few stylish women like Brooklyn shop owner Kai and Man Repeller’s Leandra. (Spoiler: They nailed it.) 

Next up, Jen—a photographer, writer and founder of the empowering website Girls I Know—who’s ditching her usual tomboy uniform of tees and jeans for some of our favorite dresses. 


 DAY ONE: THE OFF-THE-SHOULDER CHAMBRAY DRESS 

 Jen grabs a cocktail at De Maria in Nolita, NYC, wearing our off-the-shoulder chambray dress with tie waist, dandelion drop earrings and suede
lace-up pointed-toe flats


 “I wear a lot of denim, so it feels pretty natural for me to try it in dress form. I like the off-the-shoulder look too because it shows off my freckles!” 

 DAY TWO: THE MIDI DRESS IN LIBERTY® FLORAL 


 “This dress has a classically beautiful shape and is very flattering. The men’s shirt helps relax the look and keeps it from looking
too sweet.” 

 DAY THREE: THE DENIM APRON DRESS 

 Jen, at a friend’s showroom in Soho, NYC, wears our denim apron dress, new vintage cotton T-shirt and double-strap slides in snakeskin-printed leather


 “I began photographing women for the website I created, Girls I Know. I enjoy the process of shooting on film and capturing the personalities and emotions of people through that medium. I’ve worn many hats in the fashion industry, but I’ve finally allowed myself to accept the title of photographer. I don’t agree with naming oneself something without having done
it well.” 

DAY FOUR: THE STRIPED DRESS 

 Jen, at a friend’s apartment in Soho, NYC, wears our long-sleeve striped dress, Saint James® unisex Meridien II nautical T-shirt, Piper sunglasses and Biella
tassel loafers


 “Stripes are better with more stripes. This T-shirt also gave the dress a bit more shape, and the loafers polished everything off.” 

 DAY FIVE: THE LACE-UP SHIRTDRESS 

 Jen, outside Landmark Sunshine Cinema on the Lower East Side, NYC, wears our lace-up shirtdressfatigue jacketvintage crop jean in Rhodes wash and Sophia ankle-wrap pumps in suede


“In a tribute to my 2005 self, I’m trying out a dress over jeans. It helps if the lines (of the dress and jeans) are clean.” 


 Nicely done, Jen. OK, your turn. Instagram your own personal spin on dresses with the hashtag #jcrewchallenge. 

Special thanks to De Maria and Maman.

Photographs by Frances Tulk-Hart.
Hair and makeup by Summer Tran. 


Shop our entire dress collection here
TAGS: the challenge, dresses, womens, how to, new york city
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