Style Tomboy Outfits: 8 Looks to Copy and the Men's Sizes to Order Supermade Editorial 22 October 2026 10 min read The easiest tomboy outfit to copy is a loose tee half-tucked into dark barrel-leg jeans. Add cream low-top sneakers and a washed cap. What makes any outfit read as tomboy is proportion: a top with room in it over pants that fall straight or wide from the hip. Most of the pieces in the eight looks below come from our men's side. Our men's and women's charts for tops run on height and weight. Find the women's size you already buy from us and read across to the men's size charted for the same build. Your women's size with us Charted for Men's size to order XS 155 to 160 cm, 45 to 50 kg S, our smallest men's size (163 to 172 cm, 45 to 57 kg) S 160 to 165 cm, 50 to 55 kg S M 165 to 170 cm, 55 to 60 kg S for a closer fit, M (168 to 176 cm, 55 to 65 kg) for more room L 170 to 175 cm, 60 to 65 kg M XL 175 to 180 cm, 65 to 70 kg L (173 to 180 cm, 63 to 73 kg) Shop the Eight Looks Thorn Stitch Tee Raw Denim Straight-Leg Jeans Casual White Board Shoes - 1466 Embroidered Letter "a." Washed Baseball Cap Vintage-Wash Heavyweight Denim Hoodie Multi-Pocket Loose-Fit Cargo Pants Color Block Lace-Up Sneakers Anchor Guild Heavy-Gauge Zip Cardigan Pleated Tailored Casual Trousers Paint Splatter Plaid Frayed Hem Button Up Shirt Multi-Zip Insulated Boxy Fit Insulated Bomber Coat American Vintage Corduroy Slouchy Beanie Four-Point Star Denim Chunky Casual Shoes Distressed Multi-Pocket Cargo Shorts Belted Hem Faux Leather Bomber Jacket Double Waist Raw Denim Baggy Barrel Skater Jeans Contrast Stripe Embroidered Track Jacket Retro Color Matching Casual Pants In this piece How Men's Sizes Fit The Half-Tuck An Open Plaid Shirt A Hoodie for Campus Layered for Cool Weather Office Knit Night Out in Faux Leather Track Jacket on a Long Flight Shorts and Crew Socks How Men's Sizes Fit Tops Four of the tops in these looks have dropped shoulders: the tee, the hoodie, the bomber coat and the faux leather bomber. Their shoulder seams are meant to sit partway down your upper arm. If the seam reaches your elbow, the size is too big. Six of the seven tops are listed as relaxed or oversized, and the smaller of two sizes still hangs loose in those. The zip cardigan is the one regular fit; there the larger size gives you the same slouch as the rest. Sleeves and hems run long if you're under 163 cm, where our men's S starts. Four tops here can take some of that length in: the track jacket with its elastic cuffs and hem, the faux leather bomber with snap cuffs and a buckle strap at the hem, and the bomber coat and the hoodie with their ribbing. Pants There's no hip measurement on our pants charts, only waist, height and weight. We borrow Nike's body-size charts to show how men's and women's shapes differ, though its sizes aren't ours: its men's S is a 29- to 32-inch waist, ours 26 to 28. In sizes XS to L, its men's hips run 5.5 to 6 inches larger than the waist and its women's hips 9.5 inches larger. A men's pair bought by your waist size can end up tight across the seat for that reason. Here's what to order in each pair from the looks below. Pants Closure and cut Size to order Raw Denim Straight-Leg Jeans Women's cut, rigid raw denim, pre-shrunk Your waist on our women's chart, or the next size up if you're at the top of a range Multi-Pocket Loose-Fit Cargo Pants Men's, button fly, belt loops One size above your waist, belted Distressed Multi-Pocket Cargo Shorts Mid-rise, zip and button fly, belt loops One size above your waist, belted Double Waist Raw Denim Baggy Barrel Skater Jeans Oversized wide leg, two-button waist Your waist size. The oversized cut leaves room at the hips Pleated Tailored Casual Trousers Elastic waist, wide straight leg Your waist size Retro Color Matching Casual Pants Elastic waist Your waist size A US women's 6 is a 27.5-inch waist with 37-inch hips on Nike's numbered size chart. That waist is an S on our charts. The S on our women's chart runs 66 to 70 cm, though, and 27.5 inches comes to 69.9 cm, at the very top of it. Take the M in the rigid raw jeans, which won't give at the waist. Those 37-inch hips sit 9.5 inches above the waist, the women's proportion on those charts. Order M in the cargos and the cargo shorts, one size up from S, and wear a belt. The barrel jeans, the trousers and the track pants stay at S. Our men's S is charted for people 3 to 7 cm taller than our women's S. The difference shows up as extra length at the hem. Leave it stacked over your shoes on the cargos instead of hemming it. Shoes Only the 1466 board shoes have a US conversion on their product page. On that chart, EU 35 is a US women's 5, EU 36 is a 5.5, EU 38 is a 6.5 to 7 and EU 39 is a 7.5. The size list has no 37. A US 6 falls right in that gap. One buyer who wears EU 38 found the 38 a little small and suggests going up a size, while another calls the shoes true to size and good for wide feet. At a US 6 we'd take the 38. The Color Block sneakers come in EU 35 to 40, 37 included. The Four-Point Star shoes run from EU 36 to 46. There's no US conversion on either page. EU 39 on the 1466 chart matches a US women's 7.5, and the Color Block sneakers go one size past that. The Eight Looks The eight pieces below turn up in more than one look and are the ones to buy first. A plain white crew-neck tee of your own sits under three of the looks. Piece Worn in Thorn Stitch Tee The Half-Tuck and Shorts and Crew Socks in blue, Night Out in Faux Leather in black Raw Denim Straight-Leg Jeans The Half-Tuck, An Open Plaid Shirt Casual White Board Shoes - 1466 The Half-Tuck, Office Knit, Shorts and Crew Socks Embroidered Letter "a." Washed Baseball Cap The Half-Tuck, Shorts and Crew Socks Color Block Lace-Up Sneakers An Open Plaid Shirt, A Hoodie for Campus, Track Jacket on a Long Flight Vintage-Wash Heavyweight Denim Hoodie A Hoodie for Campus, Layered for Cool Weather Multi-Pocket Loose-Fit Cargo Pants A Hoodie for Campus, Layered for Cool Weather Four-Point Star Denim Chunky Casual Shoes Layered for Cool Weather, Night Out in Faux Leather The Half-Tuck White thorn line-art over washed blue cotton. Thorn Stitch Tee $59.99. Photo: Supermade. On Gildan's spec sheets for its heavy cotton tee, the adult S runs 28 inches from shoulder to hem, 2.5 inches longer than the women's S and an inch wider across the chest laid flat. A half-tuck puts that extra length to use: the front goes into the waistband and the back hangs loose. We use the blue Thorn Stitch Tee ($59.99), relaxed pre-washed cotton with dropped shoulders. Its white thorn line-art runs from the collar across the back onto the sleeves. Tuck only the front into the jeans, then ease an inch of it back out over the waistband. The jeans are the Raw Denim Straight-Leg Jeans ($77.99), a women's cut in rigid raw selvedge that fades as you wear it. They're sold as straight-leg jeans. In the product photos, though, the leg is a barrel, roomy at the thigh and curved back in at the hem. The Casual White Board Shoes - 1466 ($89.99) are perforated cream leather on a chunky sole, light enough in color to sit under dark denim. On top goes the Embroidered Letter "a." Washed Baseball Cap ($19.99) in black, a cotton twill cap whose pre-curved brim is washed blue like the tee. Its snapback adjusts to your head. Rigid selvedge denim in a barrel shape. Raw Denim Straight-Leg Jeans $77.99. Photo: Supermade.Cream leather on a chunky sole. Casual White Board Shoes - 1466 $89.99. Photo: Supermade.Black crown, washed blue brim. Embroidered Letter "a." Washed Baseball Cap $19.99. Photo: Supermade. An Open Plaid Shirt Red plaid, paint flecks and a frayed hem. Paint Splatter Plaid Frayed Hem Button Up Shirt $102.99. Photo: Supermade. Paint flecks and a frayed hem make the Paint Splatter Plaid Frayed Hem Button Up Shirt ($102.99) look worn in from the first day. It's red and white plaid, cut relaxed, in S to XL. We wear it unbuttoned over a plain white tee as a light layer for fall. Pick a tee shorter than the shirt, or it will hang out below the frayed edge. The raw barrel jeans and the Color Block Lace-Up Sneakers ($91.99) in apricot go with it. The apricot pair is beige and khaki with yellow laces. When the shirt's sleeves reach past your wrists, push them up to the forearm. A Hoodie for Campus Washed green, on a woman at left and a man at right. Multi-Pocket Loose-Fit Cargo Pants $79.99. Photo: Supermade. The extra length of the men's Multi-Pocket Loose-Fit Cargo Pants ($79.99) stacks over the sneakers of the woman on the left in this photo. They're a roomy straight cut in washed green. Blue-green is the color to pick in the Vintage-Wash Heavyweight Denim Hoodie ($79.99); of its four colors, it sits closest to the washed green of the cargos. The hoodie is a relaxed cotton blend whose ribbed cuffs and hem close it at the wrists and the bottom edge. It hides the belt if you've sized the cargos up and belted them. The Color Block sneakers handle a day of walking between classes. They sit on a lightweight EVA midsole and have a padded collar and tongue. Faded blue-green with a chest graphic. Vintage-Wash Heavyweight Denim Hoodie $79.99. Photo: Supermade.Mesh and overlays with yellow laces. Color Block Lace-Up Sneakers $91.99. Photo: Supermade. Layered for Cool Weather Over the hoodie and cargos goes the Multi-Zip Insulated Boxy Fit Insulated Bomber Coat ($154.99). It's a cotton-blend bomber, listed for layering in spring, fall and cool weather, that stops at the hip and leaves the rest of your height to the loose cargos. Its boxy cut has room for the hoodie underneath, and ribbing at the collar, cuffs and hem helps hold warmth in. Layer Piece How to wear it Coat The bomber coat in black Zipped up to the ribbed stand collar Under it The Vintage-Wash hoodie Hood pulled out over the coat's collar. It adds a layer at your neck Head American Vintage Corduroy Slouchy Beanie, $12.99 Pulled down over your ears, slouch at the back. Black, beige or dark brown Legs The cargo pants The stack at the shoe keeps cold air off your ankles Feet Four-Point Star Denim Chunky Casual Shoes, $100.99 Black canvas trimmed in faux fur, on a lug sole for grip. Wipe clean by hand only Black, with a ribbed stand collar. Multi-Zip Insulated Boxy Fit Insulated Bomber Coat $154.99. Photo: Supermade.Fine ribs and a slouchy crown. American Vintage Corduroy Slouchy Beanie $12.99. Photo: Supermade.Black canvas on a lug sole. Four-Point Star Denim Chunky Casual Shoes $100.99. Photo: Supermade. Office Knit Zipped most of the way up over a plain white crew-neck tee, a knit cardigan looks put together enough for an office without a suit rule. Ours is the Anchor Guild Heavy-Gauge Zip Cardigan ($51.99), a cotton-blend knit that comes only in purplish navy. White piping on the pockets and an anchor on the chest give it a preppy look. There's more on that style in our guide to preppy style. Tuck the tee into the trousers, or it will bunch under the cardigan's ribbed hem. Zipped up, with the anchor on the chest. Anchor Guild Heavy-Gauge Zip Cardigan $51.99. Photo: Supermade.Front pleats over a wide leg. Pleated Tailored Casual Trousers $77.99. Photo: Supermade. We pair it with the Pleated Tailored Casual Trousers ($77.99) in gray. Black suits a more formal workplace. If your dress code is strict, these are the one pair in the looks worth hemming so they just touch the top of your shoes. The 1466 board shoes finish the outfit. Night Out in Faux Leather For a night out, the Belted Hem Faux Leather Bomber Jacket ($113.99) goes over all-black clothes. The distressed faux leather is cut oversized with dropped shoulders, in S to 2XL. Snap cuffs adjust at the wrist, and a pin-buckle strap pulls the hem in at your waist. We'd buy it in coffee. The black one would disappear against everything under it. Coffee on the woman at left, black beside her. Belted Hem Faux Leather Bomber Jacket $113.99. Photo: Supermade.Black barrel leg with white stitching. Double Waist Raw Denim Baggy Barrel Skater Jeans $78.99. Photo: Supermade. Wear the Thorn Stitch Tee in black under the jacket, tucked all the way in so nothing hangs below the buckled hem. The Double Waist Raw Denim Baggy Barrel Skater Jeans ($78.99) are high-waisted and oversized, black with white topstitching. Their wide leg tapers at the ankle above the Four-Point Star shoes. Track Jacket on a Long Flight Our Contrast Stripe Embroidered Track Jacket ($109.99) has no S. It starts at M, charted for 168 to 176 cm. Someone 155 cm tall is 13 cm below that range. The elastic cuffs and hem gather part of the extra, but on anyone under 168 cm the jacket will fit like an oversized layer. Burgundy and white stripes run down the sleeves of the lightweight pale blue jacket. We wear it zipped halfway over a white tee with black track pants, the Retro Color Matching Casual Pants ($52.99). We'd pick this outfit for a long flight because of the pants' elastic waist. Reflective white piping curves down each leg, and the Color Block sneakers have reflective stitching in their laces. Pale blue with striped sleeves. Contrast Stripe Embroidered Track Jacket $109.99. Photo: Supermade.White piping on black. Retro Color Matching Casual Pants $52.99. Photo: Supermade. Shorts and Crew Socks When it's hot, swap the raw jeans for the Distressed Multi-Pocket Cargo Shorts ($72.99) and keep the blue Thorn Stitch Tee and the cap. The shorts are light blue and stop at the knee in a rolled hem. A darker version uses the shorts in gray and the tee in black. Leave the tee untucked over the shorts and wear the 1466 board shoes with white crew socks pulled up to mid-calf. Washed light blue with flap pockets. Distressed Multi-Pocket Cargo Shorts $72.99. Photo: Supermade. Sources Gildan Heavy Cotton 5000 spec sheet Pencarrie: Gildan Heavy Cotton Women's T-Shirt 5000L spec sheet Nike: Men's Bottoms Size Chart Nike: Women's Bottoms Size Chart Nike: Women's Numeric Size Chart Shop the shapes in this piece Baggy Style Wide Jeans Cargo Pants Track Pants Hoodies Jackets Hats & Caps Sneakers Women's Street Edit