Fall Outfits Men 2025: 25 Aesthetic Streetwear, Smart Casual and Old Money and Autumn Street Styles

As the crisp air of autumn rolls in, it’s time to rethink how men approach their fall wardrobe. The time of the year encourages experimentation of layering, playing with textures, creating loud statements, and wearing basic staples. Streetwear to smart casual (coats jackets) and old money (cardigans) this year there are no boundaries between casual wear, smart casual and aesthetical streetwear. Whether you’re dressing for an early autumn coffee run or a laid-back datenight, this guide showcases 25 curated looks that capture the essence of autumn mens fashion in 2025.

Relaxed Utility With a Twist

A perfect embodiment of autumn street styles, this look combines charcoal-gray overalls with a black hoodie layered underneath, offering a balanced aesthetic casual appeal. The gray beanie provides the extra warmth and also makes a slight reference to the Korean streetwear influences. Properly rolled cuffs show off traditional high-tops that are white, basic, yet good. He carries a patterned jacket casually, adding flair and a practical touch for shifting warm weather conditions.

Graphic Statement Meets Tailored Cool

This is streetwear with intention. A flashy t-shirt is fitted within high-waisted and slightly cropped brown pants to reify a contrasted look. The casual effect is kept by the white sock and the black sneakers but the look is pushed toward an autumn casual urban style by the New York cap. It’s a prime example of how Japanese and smart casual aesthetics are colliding in 2025, especially for city dwellers who value edge and structure.

Earthy Layers with Retro Sneaker Energy

This comfy casual ensemble layers a camel cardigan over a graphic tee, finished with rolled olive trousers — hitting the sweet spot of autumn mens fashion classy. The tan and white high-top sneakers provide the right amount of new age athleticism and it is supplemented by a small dose of old money when-not-at-work styling with his fitted cap. This is an outfit built for datenight or a creative office day — warm, expressive, and balanced.

Maximalist Prep With Streetwear Fusion

Blending aesthetic streetwear with European prep, this look layers a cobalt blue hoodie over an oversized shirt with statement accessories. Broad khaki trousers add balance and are a reference to Japanese oversized tailoring. The multi-striped tote and yellow glasses introduce bold color theory — a reminder that autumn is a season for confident expression.

Textured Neutrals for Transitional Weather

This is smart casual for cooler climates. An olive teddy jacket in boxy shape is paired on a tonal crewneck and tapered white jeans, making a visual contrast and making it very cozy and sophisticated. Paired with chunky white sneakers and a beige beanie, it reads like a well-edited Italian editorial — perfect for early autumn days that blend sun and fog.

Sleek Layers With Urban Edge

A masterclass in streetwear coats jackets, this look pairs a long black topcoat over a pale gray hoodie, cropped pinstriped pants, and classic black high-top Converse. The black-and-white colour scheme and delicate prints evoke the feeling of Europe meets aesthetic, but the streetwear bag Supreme strap helps to put its feet in an entirely different place. A versatile option for those who walk from café to co-working.

Plaid Over Black for Rugged Casual

A checkered flannel overshirt layered over a black hoodie and skinny ripped jeans defines this casual fall uniform. It is a proper autumn mens fashion- classic but up to date, rustic but elegant. They are made fresh yet still casual enough to go out in because of the white sneakers, one can wear such an outfit to go on an afternoon walk or get their things around campus, or even go on a datenight in colder weather. This look taps into the Korean minimalist layering trend.

Cream Cable Knit & Urban Black

Combining aesthetic cozy vibes with city styling, this outfit matches a thick cream cable-knit sweater with wide black trousers and dad sneakers. The dressed up look is enhanced with a black cap and little bling. This is peak comfy casual — a relaxed silhouette that feels right for brunch, errands, or weekend chill.

Bold Contrast and Retro Sport

With its vibrant orange jacket, this outfit is fearless yet refined. Its streetwear is black so that the jacket can shine. It is completed with tapered navy trousers and statement sneakers providing the aesthetic streetwear appeal with brands alluding to both the Japanese workwear and the 90s basketball culture. This is one of those autumn looks that demands a second glance.

Wide-Leg Vintage with a Utility Punch

Referencing baggy jeans from the Y2K revival and grounded in Japanese workwear inspiration, this outfit features oversized light-wash denim, white Puma sneakers, and a cropped tan jacket. The shirt and tie combo beneath the outerwear hints at autumn business casual, while the keychain accessory and fit make it distinctly modern.

Cozy Urban Layers With a Pop

This look is a masterclass in layering and texture for autumn mens fashion. Sand-coloured cardigan featuring dull stripe flares is a discreet lined denim shirt, with ash-hued jogger pantines, giving off a minimal-yet-comfortable casual look. The white leather sneakers add polish, while the red beanie creates a vibrant contrast, perfect for colder streetwear settings where warmth and individuality go hand in hand.

Classic Sportswear Goes Street

Fusing aesthetic streetwear and urban minimalism, this outfit pairs a crisp white hoodie with a light-wash denim jacket — an effortless combo for brisk early autumn days. There is a sporty touch to the black Nike joggers and white sneakers, which are high-top. The black beanie and crossbody bag tie it all together, offering a laid-back, city-smart solution for guys constantly on the move.

Sunlit Neutrals on the Coast

Clean, sun-washed tones make this outfit a subtle standout for warm weather autumn afternoons. The white t-shirt with a rust-colored overshirt and cream swatches of trousers combine with the white sneakers to present laid-back Italian style at its best. This outfit works brilliantly for a low-key datenight or scenic coastal stroll, proof that aesthetic doesn’t need to shout.

Cargo Cool in Earth Tones

This look leans into functional Japanese minimalism with a loose-fit brown sweater, charcoal-gray cargo pants, and ivory sneakers. The ensemble is completed with an olive green crossbody bag and a cap that is ready to go outdoors. Whether you’re hiking trails or navigating the city, it embodies autumn casual vibes with subtle aesthetic streetwear influence.

Bright Flannel With Sportswear Roots

This outfit radiates autumn street styles with its bold yellow plaid overshirt, layered over a charcoal tee and tapered black joggers. Youthfulness and sportiness are kept alive by the Nike sneakers and a Yankees cap. Ideal for transitional weekends, it bridges the gap between casual comfort and visual punch — a versatile look for everything from game day to downtown hangs.

Urban Monochrome Sophistication

Elevating autumn mens fashion classy, this monochrome ensemble pairs a sleek bomber with tailored black pants and a cream sweater beneath. The extreme contrast creates the sense of old-money affluence, yet the white minimalist sneakers make things toned down. This outfit hits all the marks for modern smart casual, ideal for rooftop dinners or downtown meetings.

Rugged Utility in Neutral Layers

This outfit leans into streetwear coats jackets and workwear tradition. Comfy layer of warm brown parka and chocolate hoodie fits perfectly on the distressed gray denim and the legendary Timberland boots. It is workmanlike, durable, and made to outdoors and do winter stuff in it the kind of appearance that feels both delicate and hardcore. An easy go-to for chilly construction zones or city streets.

Vintage Workwear Meets Playful Contrast

Effortless with a splash of color, this look pairs a powder-blue button-down with rolled olive trousers — a nod to aesthetic casual styles. The red baseball cap with layers is young and fun, as are the lace up sneakers. Whether you’re wandering a European village or grabbing espresso in Brooklyn, this ensemble speaks to Japan-inspired versatility and relaxed elegance.

Cream Turtleneck & Suede for Fall Sophistication

Tailored yet relaxed, this autumn mens fashion classy outfit revolves around texture. On top of a cream turtleneck, a camel suede jacket is posing with pleated beige trousers and tonal sneakers. It is aggressive but not rigid, an ideal business lunch on a middle working day or an exclusive opening at the art gallery. A textbook example of smart casual minimalism rooted in European styling.

Retro Knit Meets Modern Denim

This look captures aesthetic cozy in its purest form. The green sweater with a pattern is very oversized and warm, combined with wide dark color jeans, and chunky sneakers, cream-colored. Slightly tousled hair and a cross body bag round off the nonchalantly retro style. Whether sitting in a city park or walking cobblestone streets, it’s the ideal outfit for early autumn comfort with retro charm.

Relaxed Korean Streetwear Minimalism

Sometimes, less really is more. This outfit embodies an elegant Korean take on the concept of aesthetic streetlook, vested with a crisp black hooded jacket, hard-pleated khaki pants and retro-like sneakers. The combination of perfectly tailored fabrics with the casual tops is deliberately carefree, like either fall casual or simply minimal cool. The outfit is stylish and stylish, and it is perfect on hot days of summer or late early fall. No logos, no clutter—just good fit and balance.

Layered Neutrals with Street Edge

This autumn street style nails the art of layering with a refined, aesthetic casual approach. The casual background is initialized by a brown hoodie, and the padded black vest provides texture and eases of springtime adventures. This apparel is combined with charcoal joggers and a standard pair of black sneakers, providing the emanation of streetwear confidence and comfortable casualness. The slight contrast of dark outerwear and soft neutral tones does not leave it outdated and clumsy. Perfect for guys who want to keep it effortless without sacrificing structure, especially during warm weather transitions.

Graphic Smart Casual with a Vintage Edge

This fit blends classic prep with modern streetwear cues, ideal for guys wanting something both cozy and styled. A caramel brown cardigan gives a soft edge to the harshness of the graphic tee whilst the dark olive cuffed chinos keep the palette in touch with the rugged autumn mens fashion feel. The vintage palette is the ties of high-top Jordans on the vintage palette. This is your one-stop denim style on datenight, gallery openings or urban strolling. It’s an evolved form of smart casual—not too polished, but thoughtfully assembled with texture and proportion in mind.

Urban Workwear with Italian Influence

This look channels the rugged charm of Italian city streets with a modern twist on autumn mens fashion. The flash camel jacket adds a hint of old cash durability with a grey hoodie and some working-class roots over a forest-green flannel shirt to create a depth of the jacket. The distressed jean with rare knee patches refer to aesthetic streetwear, and high-top sneakers in neutral colors balance the production in the final solution of casual practicality. It’s a sharp choice for a fall coffee run or creative workday, ideal for guys balancing autumn casual comfort with downtown grit.

Earthy Tones with a Military Punch

Nothing says autumn mens fashion classy quite like a monochrome olive palette. This outfit presents an aggressive argument on the necessity of olive green in the fall of the year. The Japanese and Europe influences are united in the heavy-duty, military-style work jacket and loose-fit cargo pair of pants that feature a sense of advanced functionality. There is a fresh contrast to the crisp white tee worn underneath and the beanie and raw red boots are bringing texture and contrast. It’s aesthetic, masculine, and designed for men who appreciate minimalist streetwear coats jackets with a twist.