6 Perfect Outfits For Fellow Tomboys

This article was last updated on May 19, 2022

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You’ve never dreamed about your wedding dress, but you do have your eyes a few white Le Smokings; your most treasured family heirloom isn’t a vintage necklace from your grandma, but rather your great-uncle’s Barbour jacket he used to go hunting in; and your favorite trend from 2012 was the sneaker wedge, so you can finally stand taller than all the guys — sans stilettos. 

Yes, fellow tomboys — this feature is for you. From tried-and-true tropes, like Annie Hall, to a few more modern and unexpected dude inspirations, here are a few versions of tomboy style out there — and the perfect outfits to get you the look.

Military Spiffy — The army jacket may be a tomboy’s most beloved piece of outerwear, so really go for it with a few other sharp, tailored pieces. The key is to make sure the fit is still slim, lest you want to end up looking like a newly enlisted Charlie Chaplin.

Clockwise from top left: Elizabeth and James Kelsey Parka, $295, available at Otte; Jack Wills Gretton Bowler Hat, $148, available at Jack Wills; Junye Watanabe Rolled Ankle Trouser, $587, available at Farfetch; Monki Phoenix Blouse, $40, available at Monki; Urban Outfitters Chelsea Crew Sterling Lace Up Brogue, $49, available at Urban Outfitters.

Tinseltown Tomboy — Annie Hall, this one’s for you! We can’t do a tomboy story without referencing one of our favorite icons. Do it up modern style with patterned oxfords, thick-rimmed sunglasses, and a slim-fit vest.

Clockwise from top left: MaxMara Pescia Trousers, $305, available at Matches; The Hill-Side Indigo Herringbone Check Tie, $69, available at Steven Alan; Karen Walker Super Duper Strength Sunglasses, $250, available at La Garconne; Steffen Schraut White Claudine Smoke Sleeve Shirt, $160, available at Stylebop; The Department Tailored Waistcoat, $51.20, available at House of Fraser; Just Ballerinas Leopard Print Jazz Shoe, $234.52, available at Farfetch.

Bowery Punk — Leopard, leather, and studs = perennial punk staples. Creepers also can help give you a little height (since heels will probably never fit into your arsenal).

Clockwise from top left: Equipment Earl Bright White Leopard Print Shirt, $208, available at Equipment; Mango Biker Style Super Slim Jeans, $79.99, available at Mango;Firetrap Studded Belt, $31.66, available at ASOS; BLK DNM Cropped Motorcycle Jacket, $795, available at American Rag Cie; Dieppa Restrepo Cali Platforms, $308, available at Gargyle.

Off-Hours Mogul — Part Pharrell, part Angel Haze, this look screams Boss Lady without getting all stuffy.

Clockwise from top left: Reiss Dylan Leather Trousers, $237, available at Reiss; Opening Ceremony Exclusive Toykoa Sweatshirt, $75, available at Opening Ceremony; Patagonia Gnarwall Beanie, $39, available at Patagonia; Supra WMNS Society, $105, available at Supra; Guns, Germs, and $teal Dolla Dolla Bills Y’All Wallet, $132, available at GG$.

Grown-Up Schoolboy — While you might not have thought florals were your thing, they very well could be on a spiffy varsity jacket like this one. Cropped pants, slick loafers, and a backpack keep that Billy Elliot-vibe alive.

Clockwise from top left: rag & bone Cambridge Jacket, $795, available at rag & bone; Joseph Queen Cotton Blend Tweed Pants, $99, available at The Outnet; Madewell Perfect Chambray in Ferrous, $69.50, available at Madewell; Herschel Supply Co. Settlement, $54.99, available at Herschel Supply Co.; Bass Washington, $84.95, available at Lori’s Shoes.

Trad Dandy — Take your suits out of the office by finding one in a cropped, shrunken fit. A little silk bandanna looks cheeky tied as an ascot under a button-up (and take this as an opportunity to grow your loafer collection — we give you permission!).

Clockwise from top left: Scotch & Soda Checkered Wester Shirt with Bow Clip, $60, available at Scotch & Soda; Liberty London Tree of Life Silk Scarf, 109.71, available at Liberty; J.Crew Paley Pant in Super 120s, $98, available at J.Crew; J.Crew 1035 Jacket in Super 120s, $188, available at J.Crew; Carven Moccasins, $432.46, available at Colette.

Market Research by Willow Lindley

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