Picture this: you’re walking down a bustling city street, the crisp autumn air kissing your cheeks, fallen leaves crunching beneath your perfectly chosen ankle boots. There’s something magical about autumn in the city – it’s like the entire urban landscape becomes your personal runway, and honey, you’re ready to strut.
Ready to curate your autumn wardrobe with 10 Street style outfits that’ll have you owning every city sidewalk? Each look features the holy trinity of autumn street style: high-waisted jeans, leather jackets, and ankle boots – because some combinations are simply too good to mess with. Pin your favorites as we go, and don’t forget to follow along for more autumn outfit inspo that’ll keep your Pinterest boards looking fresh all season long!
Outfit 1: Classic Denim and Leather
Perfect for: Coffee dates, casual Friday, weekend errands
Picture yourself in dark-wash high-waisted jeans that hug in all the right places, paired with a crisp white tee that peeks perfectly from beneath your go-to black leather jacket. Slip into sleek black ankle boots and you’ve got instant cool-girl credibility.
Elevate this tried-and-true combo with oversized sunglasses – even on cloudy days, they add an air of mystery. A structured crossbody bag in matching black keeps your essentials close while maintaining clean lines. This is your “I woke up like this” outfit that actually requires zero effort but maximum impact.
Style note: Roll your jeans slightly to show off those ankle boots, and let one shoulder of the leather jacket slip casually for that effortlessly undone vibe.
Pin this look for your coffee run outfit inspiration!
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Outfit 2: Plaid and Combat Boots
Perfect for: Weekend markets, casual brunch, city exploring
Mom jeans in a relaxed fit create the perfect laid-back foundation, while a classic plaid shirt brings pattern and texture. Layer an olive green sweater over the plaid – buttoned or tied around your shoulders – for dimension and warmth. Lace up black combat boots to ground the look with edgy attitude.
Complete the vibe with a cozy beanie in a complementary neutral and a practical backpack that says “I’m ready for adventure.” This outfit screams autumn weekend energy and photographs beautifully against colorful fall foliage.
Style note: Let the plaid peek out from under your sweater at the hem and cuffs for layered perfection.
This look is trending hard on Pinterest – save it to your autumn fits board!
Outfit 3: Monochrome Minimal
Perfect for: Gallery openings, dinner dates, sophisticated outings
All-black everything gets an autumn update with rich textures and strategic layering. Start with black high-waisted jeans, add a black turtleneck for sophisticated simplicity, then throw on your leather jacket for instant polish. Heeled ankle boots elongate your silhouette and add just enough height to feel powerful.
Gold jewelry brings warmth against the monochrome palette – think delicate earrings or a simple chain necklace. A structured tote bag in black or rich brown keeps the sophisticated vibe while being practical enough for your urban adventures.
Style note: Play with textures – matte jeans, glossy leather, soft knits – to keep the all-black look interesting.
Monochrome magic never goes out of style – pin this for elegant autumn inspiration!
Outfit 4: Cozy Layered Look
Perfect for: Farmers markets, casual lunch dates, cozy weekend plans
Light-wash jeans bring a fresh contrast to autumn’s deeper tones, while a cream oversized sweater wraps you in cozy comfort. Your brown leather jacket adds warmth and richness – brown feels so right for autumn. Slip into tan or brown Chelsea boots for seamless coordination.
A plaid scarf in autumn colors ties the whole look together (literally and figuratively), while a crossbody bag keeps your hands free for pumpkin picking or market browsing. This outfit feels like a warm hug while looking effortlessly put-together.
Style note: Let your scarf drape naturally – no need for perfect styling. The beauty is in the relaxed, lived-in feel.
Save this cozy combo for all your autumn comfort outfit needs!
Outfit 5: Bold Color Pop
Perfect for: Brunch with friends, shopping trips, confidence-boosting days
Straight-leg jeans in a classic dark wash provide the perfect neutral canvas for a show-stopping mustard yellow sweater – this color is having such a moment and looks gorgeous against autumn’s natural backdrop. Your trusty leather jacket grounds the bright color while keeping the street style edge intact.
Black ankle boots maintain the look’s sophistication, while statement earrings in gold or warm tones amplify the color story. A mini backpack adds a touch of playful practicality that feels very now.
Style note: When wearing bold colors, keep the rest of your palette neutral to let the star piece shine.
Mustard yellow is everywhere this season – pin this pop of color inspiration!
Outfit 6: Edgy Hoodie Combo
Perfect for: Concerts, casual hangouts, rebellious mood days
Distressed jeans with strategic rips and fading bring street style authenticity, paired with a cozy hoodie for that perfect high-low mix. A cropped leather jacket over the hoodie creates interesting proportions while maintaining warmth. Combat boots ground the look with serious street cred.
Add a baseball cap for sporty vibes and throw on a belt bag (yes, they’re back and cooler than ever) for hands-free convenience. This outfit screams “I’m too cool to care” while actually being very carefully curated.
Style note: The cropped jacket over the hoodie creates visual interest – play with proportions for maximum impact.
Hoodie chic is having a moment – save this edgy combination!
Outfit 7: Polished Street Chic
Perfect for: Work events, after-work drinks, date nights
Elevate your street style for more sophisticated occasions with sleek black jeans, a crisp white blouse with interesting details (think subtle ruffles or unique buttons), and a tailored leather jacket that means business. Heeled ankle boots add height and confidence.
A silk scarf tied elegantly around your neck brings a touch of French-girl chic, while a structured handbag completes the polished look. This outfit seamlessly transitions from boardroom to bar without missing a beat.
Style note: Tuck the blouse partially for a modern, relaxed feel that’s still office-appropriate.
Work-to-play outfits are Pinterest gold – pin this versatile look!
Outfit 8: Denim on Denim
Perfect for: Tourist days, casual adventures, denim lover dreams
The Canadian tuxedo gets an autumn street style makeover with light-wash high-waisted jeans paired with a classic denim shirt in a slightly darker or different wash – the key is subtle contrast, not perfect matching. Layer a rich brown leather jacket over top for warmth and texture contrast.
Chelsea boots in brown or tan coordinate beautifully with the leather jacket, while layered delicate necklaces add feminine touches to balance the structured denim. A leather tote bag completes the look with practical sophistication.
Style note: Roll the sleeves of your denim shirt and leave a few buttons undone for relaxed styling.
Denim on denim done right – save this timeless combination!
Outfit 9: Sweater Weather Vibes
Perfect for: Autumn festivals, cozy dates, embracing the season
Mom jeans in a relaxed fit pair beautifully with a rich burgundy sweater – this color embodies everything we love about autumn. Layer your leather jacket over top when needed, and step into combat boots for that perfect street style edge.
A wool beanie adds cozy texture and keeps you warm during those crisp autumn mornings, while a chunky scarf brings additional warmth and visual interest. This outfit is autumn personified and photographs beautifully against colorful fall leaves.
Style note: Partially tuck the sweater for a relaxed, undone look that’s still intentional.
Burgundy is autumn’s power color – pin this seasonal perfection!
Outfit 10: Urban Athleisure Twist
Perfect for: Running errands, casual gym sessions, comfortable city days
Black skinny jeans provide a sleek foundation for a graphic tee with personality – choose designs that speak to your style, whether that’s band tees, vintage logos, or artistic prints. A leather bomber jacket brings sporty sophistication, while white ankle boots keep the look fresh and modern.
A sleek backpack serves double duty for gym gear or daily essentials, and a minimalist watch adds a polished finishing touch. This outfit proves that comfort and style aren’t mutually exclusive.
Style note: Let the graphic tee be the personality piece – keep other elements simple to let it shine.
Athleisure meets street style – pin this comfortable chic combo!
Ready to transform your autumn wardrobe? Pin this entire post to your style boards and start planning your street style takeover. The city streets are calling, and you’re about to answer in the most stylish way possible!
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