Fall is the ultimate style season for men.
Whether you’re heading to brunch, walking downtown, or lounging on a weekend getaway, dressing well doesn’t mean sacrificing comfort.
In this guide, we’ll break down 21 fall casual outfit ideas for men that are ideal for fall. Each look includes helpful style tips, seasonal variations, and suggestions so you can make it your own.
1. Denim Jacket + Hoodie + Chinos
This classic layered look is ideal for cool mornings and casual afternoons.
Why it works:
- A light or medium-wash denim jacket adds rugged structure.
- A neutral hoodie (grey, tan, or black) provides warmth without bulk.
- Earth-tone chinos (olive, khaki, charcoal) offer a clean contrast.
Style variations:
- Swap the hoodie for a thermal henley or crewneck sweatshirt.
- Try a sherpa-lined denim jacket for colder days.
- Add white sneakers for casual, or leather Chelsea boots for polish.
Accessories:
- Beanie, baseball cap, or leather watch to finish the outfit.
2. Flannel Shirt + Dark Jeans + Work Boots
Nothing says fall like a well-worn flannel shirt. This timeless combination is both masculine and approachable.
Key pieces:
- Flannel shirt in red, navy, green, or mustard.
- Dark-wash jeans (straight or slim fit).
- Rugged work boots (brown leather or suede).
Pro tip:
- Roll the sleeves and wear the shirt unbuttoned over a plain white or black tee for a relaxed vibe.
- Layer with a quilted vest or denim jacket on chillier days.
Occasion: Perfect for apple picking, weekend errands, or grabbing drinks on the patio.
3. Quilted Vest + Henley Shirt + Cargo Pants
This outfit blends outdoor function with modern streetwear edge.
Why it works:
- Quilted vests add insulation without restricting movement.
- A long-sleeve Henley offers texture and warmth.
- Cargo pants—especially in olive or tan—give utility flair and a casual vibe.
Style upgrades:
- Swap the Henley for a merino wool sweater.
- Add high-top sneakers or hiker boots.
- Top with a knit beanie or wool baseball cap.
Great for: Fall hikes, farmers markets, or weekend getaways.
4. Lightweight Bomber Jacket + T-Shirt + Slim Joggers
This casual, sporty combo is a go-to for everyday errands or casual hangouts.
Style breakdown:
- Lightweight bomber jacket in black, navy, or olive.
- Simple crewneck T-shirt (white, charcoal, or muted color).
- Slim joggers with tapered ankles in dark gray or black.
Footwear ideas:
- White sneakers for a clean streetwear vibe.
- Slip-on loafers or Chelsea boots for a more elevated casual look.
Pro tip: Choose a bomber with subtle details like ribbed cuffs, zip pockets, or a quilted lining for fall texture.
5. Knit Sweater + Cuffed Jeans + Desert Boots
This refined casual outfit is simple, versatile, and ideal for both day and evening.
Style formula:
- Textured knit sweater (cable-knit, waffle, or ribbed)
- Cuffed straight or slim-fit jeans
- Desert boots or chukkas in suede (beige, gray, or tan)
Extras:
- Add a lightweight scarf or minimalist beanie.
- Layer with a flannel shirt underneath the sweater for added depth.
Occasion: This outfit transitions well from brunch to casual date nights.
6. Corduroy Shirt Jacket + White Tee + Black Jeans
Corduroy is a fall staple that adds both warmth and texture to your outfit.
Why it works:
- Shirt jackets offer a casual outer layer without feeling bulky.
- A basic white T-shirt keeps the look minimal.
- Black jeans create contrast and add edge.
Add-ons:
- Brown boots or high-top sneakers.
- A beanie or leather strap watch for personality.
Pro tip: Go for neutral tones like camel, rust, or forest green to match the season.
7. Field Jacket + Plaid Shirt + Slim Jeans
Inspired by military utility, this outfit brings masculine vibes with fall flair.
Key layers:
- Olive or tan field jacket (waxed cotton or canvas)
- Plaid flannel or brushed cotton shirt
- Slim-fit jeans in indigo or charcoal
Style tip: Keep the shirt untucked for casual settings, or button it up for a cleaner look.
Footwear: Chukka boots or moc toe boots complete the rugged aesthetic.
8. Oversized Hoodie + Puffer Vest + Tapered Sweatpants
For those off-duty fall days, this cozy combo mixes comfort and casual style.
Why it works:
- The puffer vest adds structure without overheating.
- An oversized hoodie offers a laid-back, streetwear feel.
- Tapered sweatpants (preferably in matching or tonal color) polish the look.
Footwear: Chunky sneakers or sporty trainers.
Pro tip: Stick to muted colors like sage, sand, and charcoal for a clean palette.
9. Longline Cardigan + Turtleneck + Trousers
Elevated and artsy, this look leans more fashion-forward while still casual.
What to wear:
- Longline or shawl-collar cardigan in a thick knit
- Solid or ribbed turtleneck
- Cropped wool or pleated trousers
Style notes:
- Great for coffee shop meetups or creative industry settings.
- Leather loafers or minimal sneakers complete the ensemble.
Tip: Stick to a monochrome palette (like greys or neutrals) for maximum effect.
10. Harrington Jacket + Crewneck Sweatshirt + Dark Denim
A timeless British-inspired look with strong mid-century vibes.
Components:
- Harrington jacket (beige, navy, or burgundy)
- Classic crewneck sweatshirt
- Dark-wash denim jeans (slim or straight leg)
Why it works:
- The combo feels clean but not overly dressed up.
- You can dress it up with leather loafers or down with retro sneakers.
Optional: Add a newsboy cap or leather gloves for a refined fall look.
11. Varsity Jacket + Graphic Tee + Black Cargo Pants
Varsity jackets add sporty, vintage energy to fall outfits while offering warmth and color.
Key pieces:
- Wool or faux leather varsity jacket
- Bold graphic or band T-shirt
- Slim or straight black cargo pants
Style tip:
- Keep the jacket fitted to avoid bulkiness.
- Add retro sneakers or skate shoes to match the casual aesthetic.
Perfect for: Streetwear fans or casual weekend looks.
12. Wool Overcoat + Hoodie + Jeans
This high-low mix blends sophistication with street-ready comfort.
Why it works:
- A wool overcoat dresses up your casual layers.
- A hoodie underneath adds warmth and a relaxed contrast.
- Jeans (light, dark, or distressed) ground the outfit in casual style.
Footwear options:
- Clean white sneakers for balance.
- Combat boots for a rugged twist.
Pro tip: Choose a neutral coat—like camel, charcoal, or navy—to maximize outfit pairing.
13. Fleece Pullover + Jogger Pants + Trail Sneakers
This outdoorsy combo works for hiking or a laid-back Sunday.
Outfit formula:
- Quarter-zip fleece or Sherpa pullover
- Stretch joggers (preferably in earth tones)
- Trail runners or weatherproof sneakers
Why it’s great:
- Ultra comfortable
- Built for movement
- Adds cozy texture to your fall lineup
Add-ons: Throw on a cap or backpack to make it trail-ready.
14. Overshirt + Striped Tee + Relaxed Denim
Overshirts—also called shackets—are a go-to layering piece for early fall.
Style ingredients:
- Mid-weight overshirt (wool, flannel, or brushed cotton)
- Striped or patterned tee
- Relaxed or vintage-fit denim
Footwear:
- Low-profile boots or retro runners
Pro tip: Mix patterns carefully—keep colors in the same family for cohesion.
15. Suede Jacket + Button-Up Shirt + Slim Khakis
A more polished casual look perfect for casual Fridays or stylish dinners.
Key pieces:
- Tan or chocolate suede bomber or trucker jacket
- Casual button-up (chambray, oxford, or brushed cotton)
- Slim-fit khaki or beige chinos
Shoes:
- Brown brogues, Chelsea boots, or suede loafers
Why it works: It’s refined but still laid-back enough to feel effortless.
16. Denim Shirt + Puffer Vest + Corduroy Pants
Layering rugged textures is what fall is all about.
Why this works:
- Denim shirts provide structure and durability
- Puffer vests offer warmth without bulk
- Corduroy pants add a nostalgic, seasonal texture
Color combo idea:
- Light denim + dark vest + tan or rust cords
Finish it off:
- Wear with boots or leather sneakers for a casual outdoorsman vibe
17. Blazer + Turtleneck + Dark Jeans
Effortlessly smart without being stuffy.
Go-to pieces:
- Unstructured blazer (navy, grey, or herringbone)
- Lightweight turtleneck (black, charcoal, or camel)
- Slim dark denim or wool-blend pants
Footwear:
- Dress boots or minimalist leather sneakers
Ideal for: Dinner dates, gallery nights, or casual Fridays
18. Hoodie + Denim Jacket + Joggers
For the guy who wants streetwear that’s clean and cohesive.
Key layers:
- Neutral hoodie (grey or cream)
- Classic blue denim jacket
- Joggers in charcoal or black
Shoes:
- Retro trainers, Vans, or slip-ons
Tip: Stick to 2-3 core colors to avoid clashing tones.
19. Trucker Jacket + Flannel + Thermal Tee
A workwear-inspired combo that handles chilly days with ease.
Pieces to use:
- Canvas or denim trucker jacket
- Plaid flannel in fall hues (orange, green, burgundy)
- Thermal or waffle tee
Great with:
- Straight-leg jeans
- Moc toe or lace-up work boots
Tip: Layer with a wool scarf if the temps drop further.
20. Tech Jacket + Base Layer + Slim Cargo Pants
Functional and weather-resistant, this outfit is fall trail-to-town ready.
What to wear:
- Waterproof or wind-resistant tech shell
- Moisture-wicking base layer
- Slim-fit cargo or utility pants
For footwear:
- Trail shoes or city-ready waterproof boots
Pro tip: Keep your color palette neutral with blacks, greys, and army green.
21. Sherpa-Lined Jacket + Thermal Henley + Black Jeans
One of the warmest casual looks, ideal for late fall.
Why it works:
- Sherpa lining adds cozy contrast and bold structure
- Thermal Henley gives breathable insulation
- Black jeans keep the outfit grounded and sleek
Footwear:
- Rugged boots or thick-soled sneakers
Style note: Choose a jacket in tan, tobacco, or black for timeless fall color.
With these 21 fall outfit ideas, you’ll have no shortage of inspiration when the weather cools down.
Whether you lean into rugged layers, streetwear vibes, or polished casual, fall gives you the freedom to mix textures and elevate your everyday look.
Which one will you try first?
Tasos Moulios is the founder of Beardlong. He loves trying different beard and hair styles and blogs about them. The tips he shares come from his own experience and love for what he does.