The Boyfriend Phenomenon

Do you know how many iterations of boyfriend-style garments exist in the fashion world these days? Chances are you do because you have at one point bought or seen others wearing a sweater, jeans, blazer et al. of this variety. Maybe you’re even wearing a boyfriend cardigan right now!

I love a pair of perfectly tailored skinny jeans just as much as the next person, but the immediate comfort that I feel when I pull on my favorite grey boyfriend sweater from J. Crew (with pockets!!) is really really tough to match. “Boyfriend” garments have found their way into the forefront of daily dressing for so many women not just this in decade but in generations before. Take Diane Keaton in arguably her most recognizable and iconic role as Annie Hall. She took it to another level, stealing the heart of Woody Allen while playfully donning a white button-down shirt, vest, tie and a pair of khakis that truthfully look as if she grabbed them from a pile of laundry in Woody’s bedroom and threw them on because she was “running late,” but somehow still managed to look adorable.

Taking a page from Diane, Princess Diana, Lauren Hutton and the many women today who adamantly embrace the fact that you can look just as sexy and put together in a menswear-style blazer as you can in a skin-tight LBD, here’s to the boyfriend sweater, tee, vest, jeans, slacks, loafers, baseball cap, button-down shirt, (insert garment here).

She clearly just stole her boyfriend’s varsity jacket because she knew how instantly cool she’d look

Slouchy boyfriend jeans paired with the right heels and sweater are strikingly flattering

Navy boyfriend sweater

The perfect cashmere “Boyfriend Sweater” from J. Crew

Diane Keaton exploring dapper femininity as Annie Hall

Current/Elliot “The Boyfriend Jeans” via Shopbop.com

Just browsing for flowers looking effortless in a chambray she stole from her man

Elliot Lucca ‘Rosa’ Boot

J Brand “Boyfriend Vest”

Everlane Slouchy Pocket Ryan Tee

Princess Di completely understood casual cool style

Such an unkempt cuff can look polished with a pair of elegant heels

St. James long sleeved striped tee: quite possibly the most versatile, easy-to-wear shirt I’ve ever bought

Waist up style courtesy of Le Wardrobe d’ Husband

The wear-anytime chambray shirt. Just try to look smoother making a salad than this girl

Long Pinstripe Blazer from Zara

Lovely Lauren Hutton in a menswear button down shirt

Navy blue hats and borrowed-from-the-boys blazers via Zara

Rebecca Minkoff Iva Too Flat Loafers

Isabel Marant fisher “man” sweater

Into The Gloss’ Emily Weiss in a grey blazer a bold red lip

Unisex Chuck Taylors plus a handbag in a feminine shade of plum