8 Mens Fall Streetwear Looks to Try This Season

Marcus Dapper

Updated on:

Flat lay of blue denim jeans, black Harley-Davidson hoodie, white sneakers, and a navy baseball cap.

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How loud you want the outfit to be decides which one fits: the all-black technical look and the bomber lean on one dark color and a clean shape, while the earth-toned knit and the flannel flat lay let texture and plaid do the talking.

Start with what is already in your closet: a dark pair of pants finishes most of these looks, and the single piece worth spending on is usually the jacket or the knit.

Prices stay mid-range throughout, from a plain brown hoodie to a Carhartt-and-boots workwear setup.

1. Wide-Legged Trousers

The shearling collar adds a warm touch to this tan jacket and wide trousers. · 📷 @felix.ruess

Wide-leg trousers in brown pair easily with a tan shearling-collar jacket, because the two stay in the same warm family and let the cut do the work. A plain cap and sunglasses finish it without adding anything loud.

Keep the top half shorter or closer to the body so the width below reads as a choice. A boxy jacket over a wide leg can swallow a smaller frame, so I’d pick the jacket first and the trouser second.

2. Bomber Jacket

A black bomber jacket and trousers create a simple, cohesive look for fall. · 📷 @caparisonpk

A black bomber over a black tee and black trousers is about the easiest fall outfit I know to repeat. One color, one clean shape, nothing to match.

Because everything is dark, the details carry the look: sunglasses, a leather duffel, and shoes that are not an afterthought. I’d pick a bomber that stops at the waistband, since a longer one breaks up the line of the trousers.

Black hides wear well, which suits a mid-range budget. Spend on the jacket and keep the tee basic.

3. Structured Jackets

The structured zip jacket elevates a casual outfit while keeping it relaxed. · 📷 @aaryannn7._

Structure is what separates a brown zip jacket from a sweatshirt: a firmer collar, a cleaner shoulder, a body that holds its shape. Worn over a white tee with loose black pants, it looks deliberate without looking dressed up.

Check the shoulder seam first. It should sit at the edge of your shoulder, because loose pants already add volume and a sloppy shoulder makes the whole outfit droop.

Brown is my pick over black here. It softens the contrast against the white tee and suits fall light better.

4. Flannel and Workwear Flat Lay

The plaid flannel and Carhartt pants create a classic workwear vibe with ease. · 📷 @dressedupdenimdude

Plaid flannel, tan Carhartt pants, and brown leather boots make a workwear outfit that needs no styling tricks. Everything is built to be worn hard, so it holds up on an ordinary weekday.

Keep the metals and leathers in one brown family: the belt, the boots, and the gloves should agree.

A Brixton cap adds a casual finish, and a wallet and pocketknife are the sort of small things that make the outfit feel lived in.

The one limit is the flannel. A busy plaid wants a solid white or gray crewneck or a waffle-knit thermal underneath, never a second pattern.

5. Black Cardigan with Cream Trousers

The fuzzy cardigan offers texture while the cream trousers lighten the look. · 📷 @alexsaunes

An open black fuzzy cardigan over a black shirt gives you texture without adding any color, and cream trousers cut the darkness at the waist. Black boots and a black belt tie the bottom back to the top.

Tailored trousers matter here. A clean line in the cream keeps the fuzzy knit from looking sloppy, so choose a slim or straight leg that sits right at the boot.

Cream shows dirt, which is the cost. I’d keep these for dry days and dates over rainy commutes.

6. Earth-Toned Knit Sweater

The earth-toned knit sweater stands out against dark pants for a balanced outfit. · 📷 @sebastiaanvanwijk

Patterned knits in warm earth tones are the most forgiving sweater I can recommend, since rust, olive, and tan all sit well together and none of them fights skin tone. Dark pants beneath keep the pattern as the single focus.

Let the sweater be the only busy thing. Plain trousers, simple shoes, and no extra layers on top let the pattern show.

For a mid-range budget, this is where to spend: one good knit gets worn all season, and a dark pair of pants you already own finishes the outfit.

7. Casual Hoodie and Denim Flat Lay

The brown hoodie over a white tee makes for an effortless weekend outfit. · 📷 @1stclass.vintage

A brown zip-up hoodie over a white tee is a two-layer outfit that asks nothing of you. Light wash distressed jeans, running sneakers, and a baseball cap complete it, and the whole thing works on a normal Saturday.

The white tee does the real work. It breaks up the brown and stops the hoodie reading as a sweat suit top, so choose one that is clean and sits flat at the collar.

Let the jeans carry the wear. If the denim is already distressed, skip rips on the hoodie and keep the sneakers plain, so only one piece looks beaten up.

I’d pick brown over gray for the hoodie. It sits better against light denim, and it looks more chosen than the default.

8. All-Black Technical Streetwear

The all-black technical jacket relies on texture to maintain a sleek appearance. · 📷 @wildshell.id

Black technical streetwear starts with a hooded shell and utility pants, and it only works when every piece stays in one dark color. Texture does the talking, so the fabric of the jacket matters more than any logo or print.

Choose a hood that sits flat when down and a jacket cut with room, then keep the pants slimmer or straight so the outfit doesn’t turn into a tent. Pockets on the pants are the detail to look for.

Reflective visor glasses are the loudest piece here, and I’d treat them as optional. A plain pair of dark sunglasses gives you the same look at a mid-range budget without drawing every eye.

Put your money into the jacket and let everything under it stay plain.