The Boyfriend Shirt

The Boyfriend Shirt: How would you wear it?

Style and Life

The Boyfriend Shirt

How would you wear it?

-Jennifer Goodkind

Jennifer GoodkindAh, the Boyfriend Shirt. We go way back … though it started as a purely platonic affair. I grew up in a family where clothes made the man. My great grandfather Jacobi Press was a tailor who like many others, emigrated from Russia to escape religious persecution. Jacobi and his wife Jenny (for whom I am named) settled in New Haven, Connecticut. Home to privileged and entitled preppies, Yale’s New Haven was the stage for J. Press’ impeccably tailored and custom-made clothes, synonymous with privilege and success. My grandfather embodied the J. Press look: Custom suit, a crisp button down shirt, a pocket square (which was usually an opportunity to bring a little color into the mix) and always a tie. I would look through his closet and devise ways of adapting his wardrobe to that of a club going, girl about NYC. I could wear his button down shirts open to show a little hint of my chest or with a white T-shirt underneath and a pair of jeans. I wore his light blue shirts, with the white spread collar up, over leggings. The masculine, traditional piece mixed with feminine (and at the time, trendy and dancer inspired – think Flashdance!) was one of many ways I would establish my own sense of style and still pay homage to J. Press: “Classic with a twist.”

Fast forward to today: Scott Evan Wasserberger, owner of SEW in New York City’s Nolita, has brought a hip brand of tailoring and custom-made clothes to Mott Street where he works with his father designing suits for The Fray and The SopranosTony Sirico (and many more that he won’t divulge). Scott has a real understanding of how to make the art of fine tailoring and custom blend with today’s lifestyle. Enter The Boyfriend Shirt. Luxurious Italian cotton from Lara Piana in delicious shades of pale pink, blue and, of course, white — all with the attention to detail and styling synonymous with a custom shirt.

I recently participated on behalf of in “the Boyfriend Shirt Photo Shoot” — along with a number of other fashion writers for various sites including,,, and I was assigned a light blue spread collared button down and instructed to bring whatever best conveyed my ‘look” as an accompaniment to the BF shirt. I decided on a pair of white, zippered at the bottom Balenciaga jeans, neutral colored wood platform heels from D&G, and jewelry from my own line, J.L. Rocks. The blend of casual with the tailored shirt brought me back to my days of raiding my grandfather’s closet. The shoot was a blast. The writers and editors modeling all conveyed their own sensuality, which we collectively realized is what makes the Boyfriend Shirt so totally appealing. What’s hotter than a BF shirt with a pair of jeans? What’s sexier than a pencil skirt with a button-down and a wide belt at the waist? Each woman who sat for the photographer brought her own “sexy,” thanks to the classic tailoring of this fabulous shirt and her own style and confidence. A winning combination.

The Boyfriend Shirt is my nomination for this year’s one, much needed essential. Celebs like Jessica Biel, Reese Witherspoon, and SI swimsuit model Jessica Hart are already rocking it. The suggestion of borrowing your boyfriend or husband’s shirt after a little lovemaking goes a long way. I’ll be wearing mine this fall with a pair of jeans and the Boyfriend blazer I intend to have Scott make for me. Grandpa would be so proud!

Boyfriend Shirt

Pictured here: Andrea Grant, (Girdle Bound lingerie, vintage shoes, jewelry: her grandmother’s vintage earrings)

Jennifer Goodkind, (White Balenciaga skinny jeans, Dolce and Gabbana shoes, jewelry from her own line: J.L. Rocks:

Sharon Haver, Focus On (Vintage Circle Skirt, YSL Bolero, Maison Martin Margiela Shoes, jewelry: Hermes watch, Agnes B bracelet, vintage bracelets and necklace, Cartier and Fendi rings, Hermes Birkin Bag)

Delaina Dixon, (City of Others Jeans, Magrit Hot pink shoes, , Cheetah print bag by Sant, jewelry: Forever 21 ring and her grandmother’s necklace)

Sabrina Newman, A New Mode (H&M Shorts, Belle by Sigrid Morrison Heels, a ton of jewelry: D&G Necklace, necklace by Semi Precious Weapons, H&M necklace, 4 bangles from Anthropologie,  custom made bracelet, and Bvlgari ring)

Nicole Abramovici, Blogger/Professional Organizer (Forever 21 skirt, Ann Marino Pumps, jewelry: Rebecca Wynne customized earrings, Vintage necklaces)

Boyfriend Shirt Photo Shoot Photographer: M. David Leeds
Venue: The Eldridge
Makeup: Rukiya A Jeffers

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