Tomboy Outfits for Women That Look Effortlessly Cool

Tomboy style is all about looking like you threw on a random outfit and headed out the door. You put some thought into it, whether that’s cuffing your boyfriend jeans, wearing a fitted piece under something oversized, or adding a polished loafer to balance out a laid-back hoodie. While all of these looks feature relaxed silhouettes, each one of these 22 outfits incorporates one standout piece to give it some pizzazz.

A crisp white button down shirt with a pair of loose-fitting boyfriend jeans is a tomboy staple for good reason. The structure of the oxford shirt keeps things from looking sloppy while the baggier jeans keep the whole look from feeling too prim and proper. With white sneakers and rolled up sleeves with a half tucked in shirt, you can wear this look pretty much anywhere.

Add a little boardroom to your tomboy wardrobe with an oversized blazer worn over a soft graphic tee. Unfairly cool! The structure of a blazer (especially one with strong shoulders) instantly lends authority, but teaming it with a tee keeps things from feeling stuffy. Straight leg pants also add to the tomboy-esque vibe, incorporating more menswear-inspired pieces into the mix, but unlike boyfriend jeans, straight leg pants won’t overwhelm your frame. Finish the look with loafers or minimal sneakers, and roll up the sleeves of your blazer for extra cool girl points.

A bomber jacket is a great way to incorporate sporty elements into your wardrobe without going full-on athletic. Paired with a hoodie underneath, you still get that sporty, laid-back vibe, but the added layering gives the look some dimension. Pair the two with cargo pants for full tomboy points, because they’re roomy and feature utilitarian pockets aplenty. Step out the door in style wearing your favorite pair of chunky sneakers. Whether you keep the hood down or up, strut through your day in effortless cool.

Try layering a denim shirt over a ribbed tank for a laid-back yet considered appearance, just wear the shirt unbuttoned. Rugged workwear shirts add an effortlessly cool vibe to tomboy outfits. Throw one over a tank top for a laid-back (but not too covered up) look, and add a pair of roomy chinos for an extra dose of comfort. Loafers or flat sneakers work well here, too, and we recommend rolling up your pant leg once to give the look some structure. Keep your workwear shirt unbuttoned for maximum tomboy appeal.

The key to pulling off this look is making sure your boyfriend jeans are, indeed, boyfriend jeans, meaning they should be roomy and slouchy, to give that borrowed-from-the-guys vibe. Rugby shirts are inherently sporty, lending an almost preppy energy to tomboy looks. Look for bold stripes and that telltale collar for extra tomboyish points, and pair with a pair of boyfriend jeans to balance things out. The structure of the rugby shirt can make your overall look feel stiff, so the baggier jeans will help ease things out. This look leans more grunge than preppy, but still has all of that tomboyish energy we’re going for. Tuck just the front of the shirt slightly, add leather loafers, and you’re on your way to channeling effortless, old money sportiness.

The oversized flannel is a tomboy staple. Flannel shirts scream tomboy chic, especially when worn open over a simple tee. There’s something undeniably laid back about flannels, whether it’s their oversized silhouettes, soft fabrics, or checkered prints, because they’re inherently tomboyish. Add a pair of loose fitting jeans for a laid-back look, and make sure they’re just as roomy as your flannel so the sloppiness appears to be intentional. Chunky boots or run-down sneakers complete the look. Feeling warm? Tie your flannel shirt around your waist for extra nineties points.

Varsity jackets are equally sporty and tomboyish, lending an effortlessly cool vibe to any outfit. Lightweight enough to layer over a slim turtleneck, it adds warmth without looking bulky. It has that perfect in-between look: dressy enough to wear out of the house, but still casual. We recommend keeping the rest of the outfit relatively minimal so the jacket is the focal point, meaning a tee and straight jeans. Retro sneakers are a must-have here, and don’t be afraid to wear your collar up for extra points.

Pairing smart wide leg trousers with a casual crewneck sweatshirt is a styling trick that delivers big results. Tomboy style thrives off of mixing laid back pieces with more polished options, and there’s no better example of this than a flowy pair of dress pants and a sweatshirt. The former is structured, and the latter is sporty and soft. Chunky sneakers keep things casual, but if you tuck your sweatshirt in (just a tad at the front), you’ll look like you tried hard even though you really didn’t.

Styling is easy for a girl with a leather jacket because she has that edge and sass already built-in. It’s a perfect combination, and surprisingly wearable, too. Leather jackets are a closet staple for good reason, because they go with literally everything, and add a tough, edgy element to any outfit. We recommend wearing yours with a white tee underneath to keep things simple and let the jacket shine. Cargos add a utilitarian element, too, keeping the whole look from feeling too put together. We like leaving the jacket unzipped here, and teaming with either ankle boots or high top sneakers. Add a pair of boots or run-down sneakers to complete the look, and leave your jacket open for maximum cool girl energy.

Tomboy meets bookworm in the combination of a sweater vest and oxford shirt. The classic menswear-inspired look of an oxford shirt and tailored pants gets a tomboy twist when you add a vest on top. Not only does it keep you warmer, but it also adds a preppy edge. Let the collar and cuffs of the oxford peek out from underneath your vest for a put together look, and roll your sleeves up to the elbow for added structure. Loafers are a must-have here. Striped dress pants are a menswear-inspired option, but they don’t necessarily look overly dressy when worn with laid back pieces.

We love a good double denim look, but taking it up a notch by incorporating a denim jacket and tee combo is next level. Opt for a band tee underneath your denim jacket for extra rebellious points, ideally worn in just like your jeans. Balanced out by the jacket and jeans, this look is kept cool. There’s a bit of an edge added thanks to the tee.

Over a long sleeve tee this top can be thrown on casually. Track pants and coach jackets are athletic staples, but also have major tomboy potential. The former are inherently comfortable, and the latter are laid-back layers that are still sporty and chic. Wear them together for an athletic tomboy look that’s perfect for a day when you don’t feel like changing clothes, otherwise known as every day. Half-way zip up your coach jacket for a sporty look, and opt for retro inspired running shoes.

Nothing says tomboy chic quite like a chunky knit sweater and combat boots! The sweater is so cozy and the boots add just the right amount of edge. Oversized sweaters are inherently tomboyish, meaning they are not only roomy and comfortable, but also soft and squishy, begging to be burrowed into on chilly mornings. We love pairing them with straight leg jeans because they provide structure to balance out the sloppiness of the sweater. Combat boots keep things tough, and we also recommend rolling up your jeans to showcase your boots.

Pinstripe trousers sound fancy, but paired with a plain tee they become the coolest kind of relaxed. Half tuck in your top and slip on a pair of loafers for a put together look that still feels like you’re barely trying.

A rugged addition to the simple vest base. Has some handy pockets, but nothing flashy. A utilitarian piece. We love wearing them over waffle henleys for a sporty, outdoorsy look. Team with relaxed jeans and boots for a laid back outfit that’s still practical (hello, pockets for all your belongings).

Tomboy style is all about looking effortless and put together at the same time, and that’s exactly what this cardigan look achieves. The slouchy cardigan sweater adds coziness while keeping things laid-back and cute. Pair it with a collared shirt underneath for an effortless tomboy look with a softer, preppier twist. The cardigan is soft and oversized, dad jeans are roomy and boxy, but the collar and loafers add structure. We recommend keeping the cardigan open to let the collar peek out, and wearing either loafers or minimal sneakers.

Few pieces scream tomboy quite like overalls. They’re nostalgic, relaxed, and playful. Here, we recommend keeping things simple and unfussy by wearing them with a basic tee. We love them because you can dress them up or down, but here we’re keeping things laid-back by wearing them with a tee and sneakers. Undo one of the straps if you’d like, which adds an extra element of nonchalance.

Few layers are as cozy as a quarter zip pullover, and they’re also inherently sporty and tomboyish. Wear yours with joggers for an athletic-inspired look that’s still polished enough to be seen out in public wearing. We love leaving the quarter zip halfway undone, and teaming with retro sneakers for extra sporty points.

Pair your trench coat with a hoodie underneath for a tomboy-ish look done just cleverly enough. We like a good hoodie and trench combo because it’s unexpected and chic. The former is inherently casual, and the latter is polished and structured. Wear them together with straight jeans and sneakers for a tomboy outfit that’s still elegant and chic. Leave your trench open and let your hoodie’s hood peek out. They’re classic, go with everything, and can dress up or down an outfit.

When you want your tomboy outfits to err on the side of elegant and put together, reach for a wool overcoat. Wool coats are inherently polished, and when worn over slim layers (like a turtleneck) they look extra refined. Here, we’re leaning into the menswear-inspired aspect by wearing one with dress pants, and rolling up our shirt sleeves to keep things casual. Open-front long coats pair nicely with loafers or ankle boots to give your look a chic-yet-comfy vibe that’s polished from head-to-toe.

A puffer jacket is going to give off some sporty vibes but also a laid back, tomboy feel. When the weather’s cold and you need a jacket that’s still stylish, reach for a puffer jacket. Wear yours with wide leg jeans and chunky sneakers for a tomboy look that’s still put together, then zip up your puffer jacket when the breeze picks up.

On the other hand, a suit vest over a crisp white shirt can take tomboy all the way to dandy. And when it works, it works really well. Team with loafers and tailored pants to lean into the polished, menswear-inspired look. Tailored vests are an underrated layering piece that add sophistication and structure to a look. Loafers are the perfect finishing touch. Leave your vest open at the ends for an unexpected, fashion forward detail.

Three pieces that suit a relaxed, menswear-inspired look.

• Double Breasted Duster Trench Coat. A long trench over a hoodie and straight jeans, as in #19.
• Women’s Full Zip Hoodie. A plain hoodie for layering under the bomber in #3 or the trench in #19.
• Wide Brim Felt Fedora Hat. A hat for the wool overcoat and turtleneck in #20.