Tomboy style isn’t about borrowing from the boys. It’s about taking the relaxed ease of menswear and making it your own, with a fit and finish that feels current. Right now, that means boxy shapes, utilitarian details, and a healthy dose of graphic tees and denim, all worn with a confidence that says you’re dressing for yourself.
These outfits are for anyone who wants a look that’s comfortable and cool, without sacrificing polish. From errands to coffee runs to casual hangouts, they work because they focus on proportion and texture rather than fuss. Here are 29 ways to pull off the trend.
Baggy Olive Cargo Pants with a Graphic Tee
The baggy olive cargo pants have a relaxed fit through the leg and a slightly dropped crotch, making them the foundation of this casual street style look. A gray graphic t-shirt keeps things simple, while beige and white sneakers match the easy proportion of the pants. This suits anyone who prefers a comfortable, relaxed aesthetic; if you’re shorter, try a slightly less voluminous cut to avoid overwhelming your frame. To recreate it, look for baggy cargo pants, a graphic t-shirt, a camouflage bucket hat, and sneakers.
Denim Overalls Over a Turtleneck with Plaid Shirt
Ever wonder how to make denim overalls feel fresh instead of nostalgic? The answer is layering. Here, paint-splattered denim overalls with a baggy fit sit over a fitted black turtleneck, with a plaid shirt worn open on top for added depth. Black combat boots ground the utilitarian look, and a yellow bandana adds a small pop of color. This works for a practical layered outfit; consider the overall length if you are petite. To recreate it, look for denim overalls, a black turtleneck, a plaid shirt, and combat boots.
Graphic T-Shirt with Baggy Cargo Shorts and Beret
An oversized black graphic t-shirt sets the tone, paired with baggy cargo shorts that hit mid-thigh for a relaxed warm-weather silhouette. White and green sneakers keep the look grounded, while a green beret adds an unexpected touch that lifts the whole outfit above basic. This is a solid choice for warmer days and a street style mood; adjust the shorts length to your preference. To recreate it, look for a graphic t-shirt, baggy cargo shorts, a green beret, and sneakers.
Oversized White Jacket with Black Crop Top and Pants
A practical rule for working with volume: pair an oversized piece with something fitted. Here, an oversized white jacket creates a strong silhouette over a black crop top, which defines the waist, while baggy black pants carry the relaxed shape downward. Black boots provide a grounded finish, and a chain belt adds a subtle edge. This look suits anyone who enjoys bold proportions; make sure the pants don’t swallow you if you’re on the shorter side. To recreate it, look for an oversized white jacket, a black crop top, baggy black pants, and boots.
Navy Blazer with White Shirt and Relaxed Jeans
An oversized navy blazer in a wool-like fabric brings a tailored element to an otherwise casual outfit. It’s worn over a white button-down shirt and relaxed-fit blue jeans, creating a mix of structured and easy. White sneakers keep the whole thing from feeling too formal, and a beige baseball cap reinforces the relaxed mood. This offers a chic casual balance that works for most heights, though taller frames carry the oversized blazer especially well. To recreate it, look for an oversized navy blazer, a white button-down shirt, relaxed-fit jeans, and white sneakers.
Dark Gray Suit with Vest and Houndstooth Fedora
A structured jacket paired with relaxed fit trousers gives a dark gray suit a modern silhouette rather than a stiff one. A white dress shirt and gray vest sit underneath, keeping the line clean. Brown leather oxfords add a classic, sharp finish to the whole thing. This gray suit with vest and houndstooth fedora suits anyone after a sharp, tailored look; you can adjust the trouser length depending on your preferred footwear height. To recreate it, look for a dark gray suit, a white dress shirt, a gray vest, a houndstooth fedora, and oxfords.
Gray Jeans with Crewneck Sweatshirt and Black Blazer
Relaxed fit gray jeans and a gray crewneck sweatshirt form a comfortable base, while an oversized black blazer adds structure on top. White sneakers keep the whole thing grounded in casual territory. A stack of multiple silver bracelets introduces a subtle edge that breaks up all that neutral fabric. This works as a versatile everyday option; if you’re petite, a slightly less oversized blazer might balance the proportions better. To recreate it, look for relaxed fit gray jeans, a gray crewneck sweatshirt, an oversized black blazer, white sneakers, and a few silver bracelets.
Colorblock Velvet Top with Relaxed Trousers
Can velvet feel casual rather than formal? Yes, when it comes as a loose colorblock top in orange and navy blue. The relaxed fit charcoal gray trousers keep the look grounded, and a belt defines the waist without tightening the silhouette. White sneakers reinforce the laid-back mood. This look adds texture and color to a daily rotation; if the trousers feel too wide, try a slimmer cut for more balance. To recreate it, look for a colorblock velvet top, relaxed fit trousers, a belt, and white sneakers.
Black T-Shirt with Leather Track Pants
Straight-leg leather track pants bring an unexpected texture to a simple fitted black t-shirt. The contrast between matte cotton and glossy leather gives the outfit its edge. White shoes with a snakeskin pattern add another layer of visual interest without overwhelming the look. This suits a modern, edgy casual style; just make sure the leather pants have a comfortable rise for all-day wear. To recreate it, look for a black t-shirt, leather track pants, snakeskin patterned shoes, and sunglasses.
Gray Sweater with Long Brown Wool Coat
Start with a gray crewneck sweater and dark wash jeans, then layer a long, oversized brown wool coat on top for warmth and silhouette. Brown suede loafers and gray patterned socks bring a refined touch. The long coat creates a strong vertical line that works well for cooler months. This is ideal for chilly days; if you are on the shorter side, a coat hitting just above the knee might feel more proportional. To recreate it, look for a gray crewneck sweater, a long brown wool coat, dark wash jeans, suede loafers, and patterned socks.
Denim Overalls with Plaid Shirt Tied at Waist
The sleeves of a blue and green plaid shirt are tied around the waist of relaxed-fit denim overalls worn over a black turtleneck. This trick gives the outfit a casual, retro feel without adding bulk. Hoop earrings and yellow sunglasses keep the accessories playful. This layered look avoids the commitment of an extra jacket. To recreate it, look for denim overalls with a comfortable shoulder fit, a black turtleneck, and a plaid shirt with long enough sleeves to tie securely.
Wide-leg Jeans with Oversized Coat and Baseball Cap
The oversized black wool coat falls well past the hips, creating a strong contrast with the wide-leg blue jeans underneath. A black top keeps the base simple, while black and white sneakers ground the proportions without adding visual weight. A brown baseball cap and black quilted bag reinforce the street-style feel. This look works best when the jeans have the right break over the sneakers. To recreate it, look for wide leg blue jeans, a black top, and an oversized black coat.
Denim Overalls Over Turtleneck with Leather Jacket
Blue denim overalls are layered over a white turtleneck, with a black leather jacket worn on top for an extra layer of texture. The fitted turtleneck keeps the silhouette clean under the relaxed overalls, while brown heeled boots add a touch of height and polish. Sunglasses complete the look without overcomplicating it. This outfit mixes soft and tough textures. To recreate it, look for denim overalls, a white turtleneck, and a black leather jacket.
Cropped Button-Down Shirt with Knee-Length Shorts
How do you make a button-down feel current? Crop it at the waist and pair it with black knee-length shorts. The light blue short-sleeve shirt hits just above the shorts’ waistband, creating a clean, modern proportion. Black loafers keep the look smart and a watch and earrings add subtle polish. This silhouette is sharp and tomboy inspired without extra fabric. To recreate it, look for a cropped button-down shirt, black knee-length shorts, and black loafers.
Graphic T-Shirt with Denim Mini Skirt and Red Belt
A white graphic t-shirt with a red-trimmed collar is tucked into a blue denim mini skirt, with a red belt emphasizing the waist. Black high-top sneakers keep the foundation sporty, while a crossbody bag and scarf add casual detail. The fitted tee and A-line skirt balance each other out nicely. The look is youthful and casual with a clear waistline. To recreate it, look for a graphic tee with a fitted cut, a denim mini skirt, and a red belt.
Oversized Blazer with White T-Shirt and Slim Trousers
A practical rule for smart casual dressing: let one piece set the formality level and build around it. An oversized black double-breasted blazer in what looks like a wool blend does exactly that, worn over a simple white t-shirt and paired with slim-fit black trousers. Black and white loafers give the outfit a sharp, sophisticated finish that matches the blazer’s polish. This suits anyone after a put-together look that doesn’t feel stiff; just make sure your trousers have a clean, straight line so the proportions stay balanced. To recreate it, look for an oversized double-breasted blazer, a white t-shirt, slim-fit black trousers, and black and white loafers.
White Bermuda Shorts with Black Vest and Shirt
White Bermuda shorts have a relaxed fit that offers more coverage than standard shorts, making them a practical choice for warm-weather casual wear. Here they’re paired with a fitted black sleeveless vest over a black collared shirt, creating a layered look that reads as considered rather than thrown together. Black flat sandals keep the outfit grounded and seasonally appropriate. This works for casual daytime outings where you want something easy but not sloppy; the longer short length means you can sit comfortably without adjusting. To recreate it, look for white Bermuda shorts, a black sleeveless vest, a black collared shirt, and black flat sandals.
Black Wool Coat Over Star Print Shirt and Slim Jeans
A black wool coat with an oversized cut provides the structure here, but the real point of interest is the shirt underneath. A black shirt covered in a white star print adds a subtle graphic element that breaks up all that dark fabric without screaming for attention. Dark wash slim-fit jeans keep the lower half clean and prevent the coat from overwhelming the silhouette. This is a smart way to work a print into an otherwise neutral outfit; the stars read as playful but not childish. To recreate it, look for a black wool coat, a star print shirt, and slim-fit jeans.
Sleeveless Top with Cream Denim A-line Skirt
A cream denim A-line skirt hits a nice balance between casual fabric and classic shape, giving the outfit structure without stiffness. It’s paired with a black sleeveless top that has a side slit, a small detail that adds visual interest to an otherwise simple silhouette. Black leather boots bring a sturdy, grounded feel that matches the denim’s weight. This combination works because the fitted top and A-line skirt create a clear waist definition; the skirt’s length can be adjusted to suit your preferred proportions. To recreate it, look for a cream denim A-line skirt, a black sleeveless top, and black leather boots.
Cropped Top with Oversized Cargo Pants and Baseball Cap
How do you wear oversized cargo pants without drowning in fabric? A cropped top is the answer. A white long-sleeve cropped top shows just enough skin to define the waist while the brown cargo pants do all the volume work. White sneakers keep the whole thing casual and grounded, and a baseball cap reinforces the relaxed mood. This silhouette works because the crop length balances the generous volume of the pants, preventing a shapeless look. To recreate it, look for a white long-sleeve cropped top, oversized cargo pants, a baseball cap, and white sneakers.
Camouflage Jacket with Graphic Tee and Cuffed Jeans
A white graphic t-shirt and a camouflage utility jacket layer together over relaxed-fit blue jeans. The gray cap and brown belt keep the look grounded, while black loafers add a smart-casual contrast that stops it from reading as purely weekend wear. This is a classic casual tomboy-inspired outfit; adjust the cuff on your jeans depending on your footwear choice. To recreate it, look for a camouflage utility jacket, a white graphic t-shirt, relaxed-fit jeans, and black loafers.
Purple Velvet Suit with Patterned Shirt
Keep the fit oversized and the accessories minimal. Here, a purple velvet suit jacket and matching vest sit loosely over a patterned shirt, with a chain necklace and sunglasses as the only extras. Black dress shoes complete the bold, festive look. Statement suits work well for evening occasions when the suit proportions match your frame. To recreate it, look for a purple velvet suit, a patterned shirt, a chain necklace, and black dress shoes.
White Shirt with Tailored Shorts and Striped Blazer
Beige tailored shorts paired with a white button-down shirt create a clean base, while a striped blazer draped over one shoulder adds a polished, preppy touch. Gold flat sandals keep the finish casual and warm-weather appropriate. This offers a polished casual look for warmer days; adjust the shorts length to suit your preferred proportion. To recreate it, look for a white button-down shirt, beige tailored shorts, a striped blazer, and gold flat sandals.
Ribbed Knit Sweater with Black Trousers and Red Sneakers
An oversized beige ribbed knit sweater falls loosely over black straight-leg trousers, creating a relaxed silhouette. Bright red sneakers with white socks break up the neutral palette and add an unexpected jolt of energy. This is a comfortable, casual look where the red sneakers become the focal point. To recreate it, look for an oversized knit sweater, black straight-leg trousers, and red sneakers.
Navy Shirt with Red Wool Coat and White Pants
A navy button-down shirt and white pants sit under a fitted red wool coat, creating a strong color contrast. A fedora hat, scarf, and quilted handbag layer in more texture and polish. This offers a chic, layered look for cooler weather where the white pants brighten the whole combination. To recreate it, look for a navy button-down shirt, a red wool coat, white pants, a fedora hat, and a scarf.
Black T-Shirt with Frayed Jeans and Blue Hooded Jacket
Can a blue hooded jacket feel like the center of a look? Here, a black t-shirt and cropped frayed gray denim jeans let it take over. The jacket’s nylon finish and bright color contrast with the worn-in texture of the frayed hem. White high-top sneakers keep the whole thing grounded, and the small patterned box bag adds a bit of personality without competing. This is a straightforward way to build a casual outfit around one strong piece. To recreate it, look for a blue hooded jacket in a lightweight material, a black t-shirt, cropped frayed gray denim jeans, and white high-top sneakers.
Camouflage Jacket with Graphic Tee and Cuffed Jeans, Close-Up Take
A camouflage jacket with graphic tee and cuffed jeans works because the proportions are relaxed without being sloppy. The jacket has a roomy fit, and the dark wash jeans are cuffed at the ankle, which gives the straight leg a cleaner line. White ballet flats replace the expected sneakers, and they keep the look light and casual. A tan leather handbag and a few bracelets add subtle polish. This is a good option if you want a comfortable outfit that still feels put together. To recreate it, look for a camouflage print jacket, a white graphic t-shirt, dark wash cuffed jeans, and white ballet flats.
Gray Blazer Over Blue Turtleneck and Navy Trousers
Pairing a blazer with a turtleneck instead of a button-up makes it feel less formal. Here, a gray blazer sits over a blue turtleneck, and the navy trousers are fitted through the leg. The black loafers and crossbody bag keep the overall silhouette sharp but not stiff. The blue turtleneck adds a color contrast that stops the gray from feeling flat. This is a solid smart-casual option that offers structure without a suit. To recreate it, look for a gray blazer, a blue turtleneck, fitted navy trousers, and black loafers.
Gray Knit Sweater Over White Shirt and Distressed Jeans
Layering a gray knit sweater over a white collared shirt creates depth without adding bulk. The sweater has a relaxed fit, and the shirt collar and cuffs peek out at the edges, giving the look a finished feel. The distressed blue denim jeans keep it from leaning too preppy. A watch, rings, and a bracelet add small details that don’t distract. This is a classic casual combination that works for most proportions. To recreate it, look for a gray knit sweater, a white collared shirt, and distressed blue denim jeans.
Final Thoughts
- Pair an oversized top or jacket with a slim bottom for balance.
- A graphic tee or printed shirt adds instant personality to neutrals.
- Layering a collared shirt under a knit or sweater adds depth.
- Footwear can set the tone: try loafers, sneakers, or boots.
The key to tomboy style is finding the right fit for your body, not just copying a man’s wardrobe. Focus on sharp proportions and textures that feel intentional, and you’ll have a look that’s both comfortable and undeniably yours.
