Fall suits tomboy dressing better than any other season: relaxed layers, sturdy shoes and borrowed-from-the-boys tailoring all make sense once it's cold. The pieces getting the most wear this year are baggy denim, cargo pants, oversized blazers, workwear jackets and heavy textured knits, with relaxed tailoring and layered outerwear leading the season. I build every one of these outfits around comfort first, then sort out the proportions so nothing swallows you. Lean cleaner for a polished day, rougher for a casual one. Each of the twenty looks below can be shifted for your body, your weather and how you actually like to feel in your clothes.
Shopping the Men's Section Without Guesswork
Many of these pieces are easiest to find in menswear, and I send clients there often for chore coats, rugby shirts, flannels and carpenter jeans. The sizing works differently, though, and that trips people up more than the style does.
- Men's pants are usually sized by waist and inseam in inches. Measure a pair you love flat, then double the waist width to compare.
- Men's cuts are straighter through the hip, so if you're curvy, size for the hip and have the waist taken in.
- Men's shirts and jackets run wider at the shoulder and longer in the sleeve. The shoulder seam is the one fit point a tailor can't easily fix.
- In US sizing, men's shoes run about one and a half sizes smaller than women's, though it varies by brand.
- Buttons sit on the opposite side to women's shirts. It feels odd for a day, then you stop noticing.
I'd start with outer layers. Jackets and shirts are forgiving because they're meant to be roomy, while trousers are where the difference in cut shows most.
1. Fall Tomboy Cargo Pants Outfit
Olive cargo pants are where I'd start a tomboy fall wardrobe. Straight or relaxed, with real room through the hip and thigh; cargos cut tight look strained across the side pockets. A fitted white tee balances the volume below, and a black bomber goes on top. Black high-tops keep it casual and a canvas crossbody adds storage. On cooler days, swap the tee for a thin mock-neck or slip a thermal underneath. A black cap and simple silver watch. I keep the side pockets close to empty, because anything heavy in them pulls the pants out at the thigh. Errands, campus or an outdoor weekend.
2. Fall Tomboy Flannel Shirt Outfit
A roomy flannel adds color, warmth and texture with no effort. Worn open over a fitted charcoal tank or crew tee, so both layers show, with straight-leg black jeans to calm the plaid. Lace-up combat boots, a sturdy belt and a compact backpack. Roll the sleeves on mild afternoons, button up when it cools. Red, forest green, brown and navy plaids all read as fall. If an oversized shirt swamps your frame, I'd pick a shorter hem or tuck one front corner into the jeans to show where your waist is. Brushed flannel softens with every wash, so a stiff new shirt is worth giving a few cycles.
3. Fall Tomboy Oversized Blazer Outfit
You can look polished and keep the relaxed shape. A gray oversized blazer with a straight, slightly boxy cut over a plain black crew tee, then dark-wash baggy jeans hemmed full length. Chunky black loafers and ribbed socks ground it. The thing I check first on an oversized blazer is the shoulder: the seam can drop a little past your shoulder bone, but if it hangs halfway to your elbow, the jacket is just too big. A structured crossbody or leather tote, small hoops or a watch. Petite frames should look for a blazer ending at the upper thigh, not the knee. It moves easily from a casual office to a weekend lunch.
4. Fall Tomboy Denim Jacket Outfit
Denim on denim works when the washes are clearly different. An oversized medium-wash jacket over a cream waffle-knit henley, top buttons open, with black straight-leg jeans for contrast. Trying to match two blues almost always looks like a near-miss, so I go blue and black on purpose. Brown lace-up boots warm it up and a canvas messenger keeps it practical. Push the jacket cuffs back to show the knit. For more warmth, a thin thermal or a neutral scarf. The jacket should be easy at the shoulders without hiding your shape. Coffee runs, markets, travel days.
5. Fall Tomboy Leather Jacket Outfit
A black leather jacket sharpens any casual outfit instantly. I'd choose a roomy biker, racer or bomber cut with space for a light gray hoodie underneath, then faded straight-leg jeans and black leather sneakers or sturdy ankle boots. A small nylon crossbody and a dark beanie. Don't pile thick layers under a structured jacket; the sleeves bind and the zip won't close. A thin hoodie or zip-neck sweatshirt fits best. New leather is stiff for a few weeks before it softens and creases at the elbows. Dark brown faux leather is a softer take. Concerts and city walks.
6. Fall Tomboy Varsity Jacket Outfit
A varsity jacket can carry a whole outfit. Black, navy, burgundy or forest green, with minimal patches so it goes with more. Over a white tee, with loose charcoal trousers instead of sweatpants; that trouser swap is what keeps it from looking like gym clothes. Clean white sneakers lighten the dark colors and a cap leans into the sporty side. A black nylon shoulder bag or pouch. Trousers should skim the shoe without dragging, and the jacket's ribbed hem should land at the waist or upper hip. Wool-bodied varsity jackets shed water poorly, so I'd keep this for dry days. Campus, travel or a game.
7. Fall Tomboy Utility Jacket Outfit
A utility jacket makes sense on days full of errands and pockets. Khaki or olive cotton in a relaxed hip-length cut, over a black-and-white striped long-sleeve tee. Dark indigo carpenter jeans add more workwear, and tan hiking-style boots give traction and weight at the ankle. A brown belt and hands-free crossbody. If the jacket has an inner drawstring, cinch it a little to show your waist; that's the detail I use to keep a boxy jacket from looking like a box. For rain, a water-resistant version and weatherproof boots. Markets, road trips, busy weekends.
8. Fall Tomboy Hoodie And Jeans Outfit
Hoodie and relaxed jeans is the most dependable combination here, and it only needs a few choices to look deliberate. A heavyweight charcoal hoodie with a structured hood and little branding; thin hoodies cling and the hood flops flat. Light-wash baggy jeans that sit securely at the waist and fall straight. A white tee peeking at the hem. Black retro sneakers, a dark cap and a canvas tote or sling. If the hoodie is very oversized, I'd pick jeans a little neater at the hip so you still have a shape. A light puffer vest for colder days. Travel and long walks.
9. Fall Tomboy Sweater Vest Outfit
A sweater vest pushes tomboy style toward the scholarly side without going formal. Brown, charcoal or navy V-neck over a crisp white Oxford, collar and cuffs showing, with pleated wide-leg trousers in black or deep gray. Black loafers and ribbed socks. A structured messenger bag. Untucked looks relaxed; a partial tuck shows the waist. Oxford cloth is thick, so a full-length shirt tail can bunch under the vest; I'd tuck it and blouse it slightly. If a roomy vest feels bulky, a lighter knit with deep armholes sits better. Long wool coat on cold days. Office, campus, museum.
10. Fall Tomboy Corduroy Pants Outfit
Corduroy adds texture and keeps things comfortable. Straight-leg cords in rust, dark brown, olive or camel with a cream crewneck sweatshirt, and a navy chore jacket over it. Brown suede sneakers or lace-up boots fit the earthy palette without matching exactly. A canvas tote and a simple watch. Fine-wale looks cleaner; wide-wale has more of a vintage workwear feel. Thick cord doesn't drape like denim, so I'd take a hem up slightly rather than let it bunch heavily around the ankle. Corduroy also wears shiny at the knees over time; washing inside out slows that.
11. Fall Tomboy Chore Coat Outfit
A chore coat gives simple separates a purposeful workwear feel. Navy, brown duck canvas or faded olive, ideally with big front pockets and a slightly boxy fit. Over a heather gray sweatshirt or thermal, with relaxed ecru jeans as a lighter change from dark denim. Brown moc-toe boots and a canvas backpack. Duck canvas is very stiff at first and softens over months of wear, so I'd size for the sweatshirt, not for how it feels on day one. Cuff the jeans once to show the boots, or leave them full for a longer line. A knit beanie keeps the palette simple.
12. Fall Tomboy Trench Coat Outfit
A trench gives tomboy dressing length and movement, and covers lighter layers when the weather turns. Relaxed tan or dark olive, worn open over a navy crew sweater, with flat-front straight black trousers. Black leather sneakers keep it casual; chunky loafers polish it. A structured backpack and a plaid scarf when it's colder. Fit across the shoulders comes first; check it with your arms forward. If you're petite, a knee-length trench is easier to wear than a full-length one, which can look like it's wearing you. Tie the belt behind you when it's open so it doesn't drag. Commuting and travel days.
13. Fall Tomboy Puffer Vest Outfit
A puffer vest warms your core and leaves your arms free, which is what I want on an active day. A black or dark green quilted vest over a gray hoodie, with relaxed tan cargos. Trail sneakers or light hiking boots and a small sling bag. I'd choose a vest that ends at the hip so it doesn't add volume where the cargo pockets sit. The hood should come out over the vest collar, not get trapped underneath. For a cleaner version, swap the hoodie for a ribbed mock-neck. Cap or beanie, depending on the forecast. Sightseeing and long walks.
14. Fall Tomboy Bomber Jacket Outfit
A bomber's compact shape pairs naturally with wide pants. Cropped or hip-length in black, dark brown or muted burgundy, over a fitted white mock-neck, with charcoal wide-leg trousers and a tailored waistband. Black platform sneakers lift the hem off the ground and keep it sporty. A silver watch, small hoops and a nylon bag. Short jacket plus wide leg works because the eye reads the waist clearly; a long jacket with the same trousers turns into one big block. Keep the top fitted. For colder days, a padded bomber and a thin merino sweater.
15. Fall Tomboy Plaid Trousers Outfit
Plaid trousers give you pattern without the usual flannel shirt. Straight or relaxed in gray, brown or navy, with a subtle windowpane or check. A solid black turtleneck and a cropped denim jacket balance the tailoring with something casual. Black lace-up boots and a slim leather crossbody. The trousers are the feature, so no second print. If turtlenecks feel tight at the neck, a black crewneck knit does the same job. A windowpane check makes the leg look longer when the vertical lines are wider apart than the horizontal ones. Galleries and casual meetings.
16. Fall Tomboy Overalls Outfit
Overalls look grown-up when everything around them is clean and simple. Relaxed black or dark indigo with a straight leg, rather than a very oversized cut. A cream thermal or fitted striped tee underneath, and a brown corduroy jacket for warmth. Lace-up work boots and a knit beanie. I adjust the straps so the bib lies flat against the chest; too short and the crotch pulls up, too long and the bib folds over. Roll the hems once or leave them long for more leg. A small backpack keeps hands free. Weekend errands and outdoor days.
17. Fall Tomboy Tracksuit Outfit
A tracksuit can work for everyday wear if colors and shapes stay simple. Navy, forest green or charcoal, straight-leg pants and a clean zip jacket. A fitted white tee under the jacket, zipped partway, breaks up the solid color. Retro white sneakers and a structured crossbody, which is the piece that stops it looking like a gym run. Skip sets with several big logos. A wool cap or light beanie adds fall texture. Not into matching sets? Neutral track pants and a bomber in a similar color give the same feel. Polyester tracksuits pill at the thighs, so I'd look for a smoother, tighter knit.
18. Fall Tomboy Rugby Shirt Outfit
A rugby shirt brings bold color and a sporty shape. Heavyweight cotton in navy and cream, burgundy and gray, or forest green and white. Loose dark-wash jeans and brown suede sneakers balance the stripes. A canvas belt, a simple watch and a compact backpack. Untucked shows off the relaxed cut; a slight front tuck adds definition. Good rugby shirts are thick and hold their shape, but the twill collar is stiff and rides up at first, so keep it out over any jacket. For colder weather, a tan barn jacket on top. Campus, games, weekend lunches.
19. Fall Tomboy Monochrome Black Outfit
All black lets shape and texture do the talking. A heavyweight black tee or fine-knit sweater, relaxed black carpenter pants with visible seams or utility pockets, and a washed black denim jacket for a tonal shift. Black combat boots, a nylon crossbody and a dark beanie. Silver hardware or a thin chain keeps it from going flat. Mix finishes: soft cotton, faded denim, polished leather, matte nylon. I check all-black in daylight, because faded and fresh blacks next to each other look accidental. If it feels too severe, let a white undershirt or gray socks show.
20. Fall Tomboy Suit Outfit
A relaxed suit is tomboy dressing at its sharpest, for work, presentations or dinners. Charcoal, navy or deep brown jacket with matching straight or wide-leg trousers. Instead of a blouse, a plain white crew tee or light knit polo. Black loafers, white leather sneakers or lace-up Derbies set the formality. A leather belt, structured bag and simple watch. The jacket should skim your shoulders and the trousers break cleanly over the shoe; I'd take a suit to a tailor before anything else, since hemming and a sleeve adjustment change it more than any accessory. Split the pieces later with denim.
Baggy on Top or Baggy Below, Rarely Both
The most common thing that goes wrong with relaxed outfits is volume everywhere. Oversized hoodie, oversized jacket and wide jeans together, and your body disappears. The rule I use is one loose zone at a time, with something closer to the body to balance it.
- Wide or baggy pants: keep the top layer fitted or cropped so your waist still shows.
- Oversized blazer or chore coat: pair with straight, not wide, trousers.
- Big hoodie or sweatshirt: a slimmer jean or a slightly tapered cargo stops it reading as loungewear.
- If you love wearing everything loose, add a belt or a tucked tee so there's one visible waistline.
Shoes carry more weight than people expect. Wide pants need a substantial shoe like a chunky loafer, a lug-sole boot or a platform sneaker; a slim flat under a wide hem looks like the trousers are falling off. If you're petite, keep wide pants cropped just above the shoe so the hem doesn't swallow your foot.
Fit Matters More Than Whose Section It Came From
Tomboy dressing gets easier the moment you have a few dependable layers, comfortable pants and boots or sneakers you can walk in all day. Cargos, straight jeans, tailored trousers, flannels, hoodies, blazers and workwear jackets combine dozens of ways without a big wardrobe. What makes relaxed clothes look chosen rather than borrowed is fit and proportion, so I'd spend your effort there. Warmer base layers, weatherproof shoes or a lighter jacket adjust any of these for the day's weather. There's no single formula. Keep the combinations that fit your life and feel like you.
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