CEO and Fashion Director of Tank Magazine, Caroline Issa, is no stranger to the power of a perfectly-cut boyfriend shirt. She takes us through her journey with the icon of her wardrobe…

Wedding pictures
Blue cashmere sweater

It was the sublime Audrey Hepburn in an oversized men’s tuxedo shirt and nothing else padding around her flat the morning after a big night in the film Breakfast at Tiffany’s that sealed the oversized boyfriend shirt as a true sartorial icon for me. White, crisp cotton, large cuffs, collarless with a bib and black, contrast buttons — total sartorial perfection. It was a nonchalant look, a statement of luck and lust and upending tradition. “Oh, this shirt? I just found it on the floor after last night’s adventures!” It symbolized breaking the rules of masculine/feminine wear in the early 1960s and forever since that moment I saw her lover’s shirt’s starring role in that scene, I started hunting down other large, crisp cotton shirts to fill my wardrobe and take center stage.

There is something quite satisfying about taking what was a traditional professional menswear suiting staple — the crisp shirt worn under a power suit tailored say, on Savile Row — and subverting it for more than just power moves on Wall Street. I’ve gone to many a cocktail party not in the mood to wear a dress, and I find adding a bold pair of earrings with an oversized shirt buttoned up all the way, collar up, and tucked into a voluminous skirt is as much a statement as a gown. Sharon Stone went even bolder with her crisp white shirt fully unbuttoned, tucked into a satin, lilac skirt for the Oscars in 1998! And I love how Jenna Lyons wears an oversized Oxford shirt these days fully unbuttoned tucked into her jeans, with flashes of skin and jewelry, less preppy and more sensual despite its thick, crisp cotton fabric. 

Blue cashmere sweater

I do have a collection myself of quite traditional blue-pinstriped with button-down collared shirts in varying shades and stripes (it IS possible to be addicted to striped shirting!), but I’ll style them differently. Sometimes layered on top of a horizontal marinière tee, tucked into a pair of khaki trousers or buttoned all the way to the top except the last two bottom buttons, cinched in at the waist over a long-pleated skirt to give more volume from the top. I also have a myriad of baby pink and lemon sorbet shirts — colors not usually associated with the boyfriend shirt, that I’ll style for day or night. The artist Georgia O’Keefe always inspires me with her masterful balance of the masculine and feminine way of dressing, and I love the way she would roll up her sleeves just so or play with the proportion and cut of a collar and color.

The quality of a great investment piece is its versatility, and I’ve styled my oversized shirts in so many ways, it’s return-on-investment has been wholly proven. And with so many designers now playing with the traditional elements to the shirt — whether collars are flipped over, mismatched sizing, cuffs are oversized, or fabrics are mixed — there is no end to the desirability of a new boyfriend shirt. Marni, Altuzarra, The Row, Victoria Beckham and Rokh all have oversized shirts that emphasize different elements to show some personality — whether an antique rose color, a turnover collar with side buttons on the shoulder, or a play on the pinstripe in reds, pinks and burgundies, there is something for everyone no matter how you want to style it.  Who knew one could reinvent a classic time and time again? 

With so many shirts in my closet, nowadays I treat them to a bit of a bespoke upgrade. I’ll get them embroidered with my initials or those of my loved ones on the bottom left-hand side, usually placed where the initials are not visible when worn under a jacket.  It used to be that men’s shirts were embroidered with their initials in order to identify them at the laundry, but for myself, the tiniest embroidered initials on my shirts give me a bit of soulfulness and comfort, and a way to make my shirts a part of me, rather than just a piece of clothing. I like that they hark back to the traditional but knowing that I try to live my life stepping out of the expected boxes, my oversized boyfriend shirts come along for the ride that is this adventure of life. So, thanks for that, Audrey!