23+ Cool Outfits Ideas For Men: Streetwear & For Classy Looks

In this post, you’ll find cool outfit ideas for men that are stylish, easy to wear, and work across different settings.

From laid-back weekend looks to polished everyday fits, these combos keep things simple, sharp, and effortlessly put-together.

1. White Crewneck T-Shirt + Khaki Chinos

This one hits clean lines without trying too hard. The white tee keeps it sharp underneath, while the overshirt adds structure without feeling stiff. Sleeves are relaxed, hem drops just right over neutral chinos.

You could button it up, but it looks better open and easy. Not too beachy, more like coast-town casual.

2. Brown Short-Sleeve Button-Up Shirt + Black Tailored Shorts

This one keeps things clean without looking stiff. The shirt’s soft and drapes easy, sleeves rolled just enough, hem untucked for balance.

Shorts stay fitted but not tight, with a solid structure that doesn’t cling.
Swap slides for low sneakers if you’re walking further.

We love this for weekend markets, iced coffee runs, or just hanging poolside with zero plans.

3. Overshirt Striped Casual T-Shirt

The olive utility overshirt offers a structured yet relaxed layer, perfect for transitional weather. Its multiple pockets add both functionality and a rugged style element. Simple striped T-shirt, the look feels modern, youthful, and easy to wear for casual outings.

4. Mustard Sweater + Beige Trousers

The sweater does the heavy lifting, warm color, boxy cut, while the trousers stay relaxed and neutral.

Keep everything else minimal like black shoes, a clean bag, nothing flashy.
It’s sharp in an offbeat way, like you didn’t try too hard (but knew exactly what you were doing).

We love this for cool-weather city walks, low-lit cafés, or anywhere it might rain just a little.

5. Linen Blazer + Matching Trousers

Wearing one color head to toe always feels intentional.

Keep the blazer loose and the sleeves pushed or rolled. Let the trousers drape without sharp creases.

A tank underneath adds just enough edge without overcomplicating it.

Best worn on a slow afternoon when you’re museum-hopping, grabbing espresso, and not in a rush to be anywhere.

6. Dark Shirt Jacket + Black Joggers

A shirt jacket like this hits that sweet middle ground between structured and casual.

Worn buttoned over a black tee, it gives off a clean, no-nonsense feel without being stiff.

White sneakers and a knit beanie keep it approachable, not overstyled.

Ideal for afternoons when you’re grabbing wine, picking up a few things, and just moving through the city like you’ve got time.

7. Navy Sweater + Slim Beige Chinos

This one’s clean and classic, but the fit is what makes it feel sharp.

The sweater hugs just right without being tight, and the chinos hit that tailored-but-not-restrictive zone.

Crisp white sneakers and a tucked collar keep the whole thing polished without looking stiff.

Perfect for those in-between days when you’re catching lunch outside, then heading somewhere you don’t want to look underdressed.

8. Bold Floral Shirt + Slim Black Trousers

This one’s loud up top but grounded where it counts. The floral shirt does all the talking, so keep it tucked and let the trousers stay clean and fitted.
White sneakers keep it fresh.

A chain or watch is all you need if you’re feeling extra.

Best worn on warm city days when you’re out for a drink, a little attention, or both.

9. Tan Bomber Jacket + White Joggers

This combo hits that cozy-sporty vibe without looking like gym wear.
The neutral hoodie layers clean under the bomber, and the joggers stay tapered without feeling tight.

Off-white sneakers pull it all together without adding noise. Great for coffee runs, slow mornings, or just stepping out when comfort’s the priority but you still want to look put-together.

10. Plaid Overshirt + Brown Cargo Pants

The oversized plaid shirt keeps it loose, while the graphic tee adds just enough personality.

Cargo pants bring in structure without making it too serious, and the sneakers keep it rooted in streetwear.

Solid for weekend hangs, record store stops, or just walking around with no agenda and good music in your ears.

11. Textured Grey Sweater + Olive Cargo Pants

The muted color combo does all the work here without needing extra layers.
The sweater’s slightly oversized and soft, while the cargos are loose and utilitarian without feeling bulky.

Black trainers keep it functional. The cap and backpack finish it off like you didn’t overthink it. Best for those city days when you’re in and out of places but want to stay comfortable and look steady.

12. Tan Suede Bomber + Black Slim Jeans

The suede jacket gives this just the right amount of polish without leaning too dressed-up.

Everything underneath stays fitted and dark, which makes the texture on top really stand out.

Brown lace-up boots pull it together while keeping the vibe grounded.
Solid pick for crisp fall mornings, rooftop catchups, or those quiet days where you still want to look like you planned it.

13. White Oxford Shirt + Straight Blue Jeans

Everything here is simple, but it lands because the fit’s dialed in. The shirt’s worn open over a plain white tee, sleeves casually rolled. Jeans are classic, no distressing, no drama.

Neutral suede sneakers keep the vibe effortless.

Perfect for those slow studio days, last-minute plans, or when you want to look good without thinking too much about it.

14. Navy Polo Shirt + Tailored Navy Trousers

The polo’s fitted without being tight, and the trousers stay clean with just enough drape.

Add sunglasses and a sleek watch to round it out without overdoing it.

Ideal for sharp summer mornings, quick client meetups, or the kind of day where you don’t have to explain your style.

15. Black Camp Shirt + Wide-Leg Trousers

All-black looks can go flat, but this one pops thanks to the shape and contrast.

The camp shirt sits loose and sharp, while the trousers give a clean break without clinging.

Chunky white sneakers and bold accessories bring the whole thing to life.
Ideal for shopping runs, gallery stops, or flexing just a little when you’re out in broad daylight.

16. Tiger Print Shirt + Black Dress Trousers

This shirt’s not shy — and that’s the whole point. With a loud print like this, everything else stays cool and tailored. Trousers are clean and high-waisted, shoes polished but unfussy.

A slim chain and sunglasses finish it off without taking it over the top.
Perfect for walking the city like it’s your runway, especially when the sun’s out and the crowd’s watching.

17. Fitted Black Tee + Light Wash Skinny Jeans

This one’s all about showing shape without doing too much.
The tee fits snug across the chest and arms, while the jeans stay tight but clean through the legs.
White sneakers balance it out and keep the whole thing looking crisp.
Perfect for casual weekends, grabbing a bite post-gym, or just walking like you own the sidewalk.

18. Linen Short Sleeve Shirt + Olive Drawstring Pants

This one’s built for heat without sacrificing style. The shirt stays open and relaxed, showing skin without trying too hard. Pants are cuffed and loose, made to breathe.
Leather sandals and a few rings make it feel lived-in and cool.
Best for slow afternoons, shady garden corners, or anywhere with sunlight and no deadline.

19. Denim Jacket + Striped Corduroy Trousers

Nothing too polished here, and that’s exactly the point.

The vintage-style jacket pairs well with the slouchy striped cords, giving it that bookstore-on-a-Tuesday vibe.

A striped tee underneath keeps the pattern play subtle, while beat-up Converse finish the look without trying.

20. Striped Camp Collar Shirt + White Tailored Shorts

The stripes bring the energy, the white shorts keep it grounded.

Leave the shirt unbuttoned a bit for airflow and attitude. Keep the fit loose but not sloppy.

Minimal jewelry and a watch are more than enough here.
This is what you pack for hotel balconies, poolside drinks, and afternoon walks that turn into golden hour.