Fall Outfits Street Styles: 29 Trendy Ideas

Fall fashion is all about embracing the transition from summer's light fabrics to the cozier, layered looks of autumn. Whether you're strolling through the busy streets of NYC or enjoying a casual day in La, the right outfit can make all the difference. In this article, we'll explore a variety of fall outfits street styles, breaking down each look to help you create your own unique fall wardrobe. Ready to get inspired?

Chic Urban Explorer

Fall is the perfect time to experiment with layered looks that offer both style and warmth. This outfit combines a Chicago graphic sweatshirt with a long denim skirt and knee-high black boots, creating a casual chic vibe that’s both comfy and trendy.

• Graphic Sweatshirt: This beige sweatshirt features bold text representing major cities like Chicago, New York, and Paris. It's perfect for those who love to travel or want to showcase their urban style. The relaxed fit makes it suitable for various body types.
• Long Denim Skirt: The high-waisted denim skirt features a daring front slit, adding a touch of edginess to the outfit. It's practical for fall, providing coverage while allowing for movement.
• Black Knee-High Boots: These boots are a fall staple, adding both style and warmth. They pair well with the skirt's slit, creating a balanced look.

To enhance this look, consider adding a black leather jacket for an extra layer of warmth and style. Avoid over-accessorizing; the bold graphic on the sweatshirt should be the focal point.

Bold Street Statement

For a bold, eye-catching look, this outfit features a striped turtleneck sweater paired with black shorts and striking red thigh-high boots. It’s a great example of how to mix classic pieces with standout accessories.

• Striped Turtleneck Sweater: The black and white stripes add a classic touch, while the turtleneck design keeps you warm. It's a versatile piece that can be styled in many ways.
• Black Shorts: High-waisted and fitted, these shorts provide a sleek base for the outfit. They contrast nicely with the oversized sweater.
• Red Thigh-High Boots: These boots are the star of the show, adding a pop of color and a daring edge to the look. They’re perfect for those who want to make a statement.

To tone down the boldness, swap the red boots for black ankle boots. Adding a black beret could also enhance the European autumn vibe. Avoid pairing this look with too many accessories, as it could become overwhelming.

Timeless Trench Layers

This outfit is a masterclass in layered dressing, combining a long beige trench coat with a simple white tee and black leggings. It’s a look that’s both practical and stylish, perfect for a day out in York.

• Beige Trench Coat: A timeless piece, the trench coat adds elegance and warmth. Its neutral color makes it versatile for any outfit.
• White Tee: Simple yet effective, the white tee is a staple that provides a clean base for the layers.
• Black Leggings: Comfortable and sleek, black leggings are perfect for casual days. They balance the bulkiness of the trench coat.

Adding a pair of chunky sneakers can give this outfit a casual comfy touch, ideal for long walks or casual outings. A statement bag or bold earrings can elevate the look without taking away from its simplicity. Avoid heavy scarves as they can clash with the trench coat's sleek lines.

Timeless Trench Elegance

A classic beige trench coat is always a fall favorite, and this outfit demonstrates how to keep it effortlessly stylish. The trench is paired with a crisp white shirt and black trousers, creating a look that is both professional and timeless, perfect for a stroll through Nyc or York.

• Beige Trench Coat: This timeless piece adds a sophisticated layer to any outfit. Its neutral tone ensures versatility, making it a wardrobe staple.
• White Shirt: The crisp, white shirt underneath adds a clean and polished look. It's slightly oversized, offering a relaxed yet chic vibe.
• Black Trousers: The fitted black trousers provide a sleek contrast to the oversized shirt and flowing trench, ensuring the look remains balanced and flattering.

To elevate this look further, consider adding a pair of chunky sneakers for a casual comfy twist, making it suitable for all-day wear in the city. Avoid adding too many accessories, as the simplicity of the outfit is part of its charm.

Sporty Chic Streetwear

This look is a perfect blend of sporty and chic, featuring a white cold-shoulder top, black track pants with side stripes, and edgy accessories. It's a great example of casual chic that's ideal for a day out in La or Chicago.

• White Cold-Shoulder Top: This top is a modern twist on a classic piece, with cut-out shoulders adding a stylish edge. It's both comfortable and trendy, ideal for various casual settings.
• Black Track Pants: The track pants with white side stripes bring a sporty element to the outfit. They're comfortable and versatile, suitable for a variety of activities.
• Edgy Accessories: The black cap and statement earrings add a touch of attitude, completing the sporty chic look.

To add a bit more flair, you could swap the track pants for a black tennis skirt and chunky sandals, perfect for a fall transition look. Avoid adding a jacket as it might make the outfit too bulky.

Bold Red Statement

This bold outfit features a striking red trench coat paired with a white tee and a black mini skirt. It's a head-turning look that's perfect for making a statement in the streets of Hong Kong or Philippines.

• Red Trench Coat: The vibrant red color of the trench coat is the focal point of this outfit, adding a pop of color that stands out against the more neutral tones of fall.
• White Tee: The simple white tee underneath balances the boldness of the trench, providing a clean and minimal base.
• Black Mini Skirt: The black mini skirt adds a touch of elegance, contrasting nicely with the bright red coat. It's a versatile piece that works well with various tops and accessories.

To make this outfit even more unique, consider adding a pair of chunky sneakers for a casual chic vibe or chunky sandals for a warmer day. Avoid adding heavy jewelry as it might distract from the boldness of the trench coat.

Monochrome Elegance

This stunning outfit showcases the elegance of monochromatic dressing, featuring rich brown hues from head to toe. The ensemble includes a brown sweater, a long flowy skirt with a high slit, and matching accessories, creating a cohesive and sophisticated look ideal for an autumn city day.

• Brown Sweater: The fitted brown sweater provides a sleek top layer, complementing the flowy skirt. It's perfect for cooler weather and adds a touch of warmth.
• Long Brown Skirt: The skirt features a high slit, adding a daring element to the otherwise conservative look. It's great for showing off a bit of leg while keeping the rest covered.
• Matching Accessories: The outfit is completed with black loafers and a structured black clutch with a chain strap, adding a modern edge to the classic ensemble.

To enhance this look, consider adding a beige trench coat for added warmth and sophistication. Avoid over-accessorizing; the simplicity of the monochrome palette is what makes this outfit stand out.

Cozy Gray Ensemble

This outfit exemplifies the perfect balance between cozy and chic, featuring a gray off-the-shoulder sweater paired with a matching maxi skirt. The look is both comfortable and stylish, making it ideal for a casual day out in Nyc or Europe.

• Gray Off-the-Shoulder Sweater: The oversized, off-the-shoulder design adds a touch of effortless elegance. It's warm and cozy, perfect for a fall day.
• Gray Maxi Skirt: The matching maxi skirt completes the monochrome look, providing a streamlined silhouette. The knit fabric adds texture and interest.
• Casual Accessories: The outfit is paired with a black cap and statement earrings, adding a sporty yet chic vibe to the ensemble.

To elevate this look, consider adding a pair of chunky sneakers or chunky sandals for a modern touch. Avoid heavy outerwear as it might detract from the sweater's unique neckline.

Red Haute Couture

This bold and vibrant outfit features a red corset top paired with high-waisted light-wash jeans and a matching red blazer. It's a statement look that exudes confidence and style, perfect for a night out in La or Chicago.

• Red Corset Top: The structured corset top adds a bold and sexy element to the outfit. It's eye-catching and perfect for making a statement.
• Light-Wash Jeans: The high-waisted jeans provide a relaxed contrast to the fitted corset, creating a balanced and stylish look.
• Red Blazer: The matching red blazer adds a layer of sophistication, tying the whole outfit together.

To make this look even more unique, consider adding a pair of chunky sandals or chunky sneakers for a street style edge. Avoid heavy jewelry as it might compete with the boldness of the outfit.

Urban Pastel

This stylish ensemble features a pink cropped jacket paired with relaxed-fit jeans and pastel pink heels. The look is elevated with a colorful scarf and matching cap, creating a playful and trendy outfit perfect for a day out in Tokyo or Hong Kong.

• Pink Cropped Jacket: The jacket is a standout piece, adding a pop of color and structure to the outfit. It's stylish and perfect for layering.
• Relaxed-Fit Jeans: The jeans provide a casual and comfortable base, balancing the boldness of the jacket.
• Pastel Pink Heels: The heels add a feminine touch, elevating the casual jeans and making the outfit more polished.

To enhance this look, consider adding a turban or more statement jewelry for added flair. Avoid overloading on accessories as the colorful scarf and cap already provide a lot of visual interest.

Retro Chic

This retro-inspired outfit features a colorful one-shoulder top paired with a brown leather midi skirt and blue textured boots. The look is finished with a stylish beret, creating a unique and fashion-forward ensemble ideal for a fashion event in Europe or Japan.

• Colorful One-Shoulder Top: The top is a bold and eye-catching piece, adding a modern twist to the retro look.
• Brown Leather Midi Skirt: The skirt adds a touch of sophistication and texture, balancing the boldness of the top.
• Blue Textured Boots: The boots add an unexpected pop of color and texture, making the outfit even more unique.

To enhance this look, consider adding a beige trench coat for added warmth and sophistication. Avoid adding too many colors as the outfit already has a lot of visual interest.

Vibrant Street Style

This vibrant street style outfit features an orange faux fur coat paired with light-wash jeans and orange sneakers. The look is completed with a beige crop top and a matching beige cap, creating a bold and playful ensemble perfect for a day out in Nyc or Cali.

• Orange Faux Fur Coat: The coat is the focal point of the outfit, adding a bold and vibrant touch.
• Light-Wash Jeans: The jeans provide a casual and comfortable base, balancing the boldness of the coat.
• Orange Sneakers: The sneakers tie the look together, adding a playful and sporty element.

To elevate this look, consider adding a pair of chunky sneakers or more statement jewelry for added flair. Avoid overloading on accessories as the faux fur coat already provides a lot of visual interest.

Urban Beige

This chic and minimalist outfit features a cropped beige jacket paired with high-waisted snake print pants. It's a sophisticated yet casual look that's perfect for a fall day in the city.

• Cropped Beige Jacket: This jacket adds a structured and modern touch to the outfit. Its cropped length makes it ideal for pairing with high-waisted bottoms.
• Snake Print Pants: The high-waisted pants with a snake print pattern bring an element of uniqueness and edge to the ensemble. They are both stylish and comfortable.
• Neutral Accessories: The outfit is completed with a beige cap and a white designer handbag, adding to the sleek and cohesive look.

To enhance this look, consider adding a pair of chunky sneakers or chunky sandals for a casual comfy touch. Avoid over-accessorizing as the snake print pants are already a statement piece.

Pink Power

This bold pink ensemble is perfect for making a statement. It features a pink blazer dress paired with pink furry boots and a matching beret, creating a playful yet sophisticated look.

• Pink Blazer Dress: The blazer dress is tailored to perfection, offering a structured and chic silhouette. The belt cinches the waist, adding definition to the outfit.
• Pink Furry Boots: These boots add a fun and whimsical element to the look, making it perfect for a fashion-forward individual.
• Matching Beret and Sunglasses: The beret and sunglasses add a touch of Parisian flair, completing the outfit with a stylish edge.

To add more depth to this look, consider incorporating a pair of chunky sneakers for a more laid-back vibe. Avoid adding heavy jewelry as the outfit is already quite bold.

Casual Pink

This casual yet stylish outfit features an oversized pink striped shirt paired with denim shorts and pink sneakers. It's a laid-back look that's perfect for a day out in Cali or Ny.

• Oversized Pink Striped Shirt: The shirt adds a relaxed and comfortable vibe to the outfit. Its oversized fit makes it perfect for a casual day.
• Denim Shorts: The high-waisted denim shorts are a classic piece that pairs well with the oversized shirt, creating a balanced silhouette.
• Pink Sneakers and Socks: The pink sneakers and matching socks add a cohesive and playful touch to the look.

To elevate this outfit, consider adding a graphic tee underneath the shirt for an extra layer of style. Avoid over-accessorizing as the simplicity of the outfit is its charm.

Monochrome Comfort

This cozy and comfortable outfit features a gray oversized sweatshirt paired with white lace pants. It's a perfect combination of casual and chic, ideal for a relaxed day out.

• Gray Oversized Sweatshirt: The sweatshirt adds a cozy and laid-back vibe to the outfit. Its oversized fit makes it incredibly comfortable.
• White Lace Pants: The lace pants add a touch of elegance and femininity to the look, balancing the casualness of the sweatshirt.
• Simple Accessories: The outfit is completed with white sneakers, adding to the casual and comfortable feel.

To make this look more unique, consider adding a pair of chunky sneakers for a modern touch. Avoid heavy jewelry as the lace pants already provide enough detail.

Patchwork Trendsetter

This stylish outfit features a patchwork shirt paired with denim shorts. The combination of different patterns and textures creates a unique and eye-catching look.

• Patchwork Shirt: The shirt is a statement piece with its mix of different patterns and textures. It's perfect for adding a touch of uniqueness to any outfit.
• Denim Shorts: The high-waisted denim shorts are a versatile piece that pairs well with the bold shirt, creating a balanced look.
• Simple Accessories: The outfit is completed with minimal accessories, letting the patchwork shirt take center stage.

To enhance this look, consider adding a pair of chunky sandals for a casual yet stylish vibe. Avoid adding too many accessories as the patchwork shirt is already a standout piece.

Beige Beauty

This elegant and understated outfit features a beige patchwork shirt paired with matching shorts. It's a sophisticated and stylish look that's perfect for a day out in York or Europe.

• Beige Patchwork Shirt: The shirt is a beautiful blend of different beige tones and textures, adding depth and interest to the outfit.
• Matching Shorts: The shorts are tailored to perfection, creating a cohesive and polished look.
• Delicate Accessories: The outfit is completed with delicate gold jewelry, adding a touch of elegance.

To elevate this outfit, consider adding a beige trench coat for added warmth and sophistication. Avoid heavy accessories as the subtle details of the outfit should be the focus.

Floral Blazer Dress

This stylish outfit features a floral blazer dress paired with beige ankle boots, creating a chic and feminine look perfect for a day out in the city.

• Floral Blazer Dress: The blazer dress is adorned with a delicate floral print, adding a touch of femininity to the structured silhouette. The oversized fit and ruffled details on the sleeves add a modern twist.
• Beige Ankle Boots: The suede ankle boots complement the soft tones of the dress, providing a neutral base that keeps the look cohesive and elegant.
• Minimal Accessories: The look is completed with minimal jewelry, letting the floral print take center stage. A simple necklace adds a touch of elegance without overwhelming the outfit.

To elevate this look, consider adding a wide-brimmed hat for a more sophisticated touch. Avoid adding bold accessories as they might clash with the delicate floral pattern.

Gingham and Denim

This casual and trendy outfit features a blue gingham oversized shirt paired with high-waisted baggy jeans and a white crop top. It's a perfect example of casual comfy style that's great for a relaxed day out.

• Blue Gingham Oversized Shirt: The shirt adds a touch of retro charm with its gingham pattern. The oversized fit makes it comfortable and easy to wear.
• High-Waisted Baggy Jeans: The jeans provide a laid-back vibe with their loose fit, balancing the more structured look of the shirt.
• White Crop Top: The crop top adds a modern and youthful touch, keeping the outfit fresh and trendy.

To add more style to this look, consider accessorizing with a pair of chunky sneakers and a baseball cap for a casual chic vibe. Avoid adding too many layers as the oversized shirt already provides enough coverage.

Cozy Gray Set

This comfortable and stylish outfit features a gray hoodie and sweatpants set, layered with a plaid shirt and accessorized with a beanie. It's the perfect look for a casual and cozy day out.

• Gray Hoodie and Sweatpants: The matching set is both comfortable and stylish, perfect for a relaxed day. The loose fit adds to the cozy feel.
• Plaid Shirt: Tied around the waist, the plaid shirt adds a touch of pattern and breaks up the monotony of the gray set.
• Beanie and Sneakers: The gray beanie and white sneakers complete the look, adding a touch of casual style.

To enhance this look, consider adding a denim jacket for an extra layer of warmth. Avoid heavy accessories as the layered look is already visually interesting.

Monochrome Plaid

This stylish outfit features a black and white plaid shirt paired with oversized gray pants and a white t-shirt. It's a modern and edgy look perfect for a street style enthusiast.

• Black and White Plaid Shirt: The shirt adds a touch of pattern and texture to the outfit. It's oversized fit makes it comfortable and easy to layer.
• Oversized Gray Pants: The pants provide a relaxed and laid-back vibe, balancing the more structured look of the shirt.
• White T-Shirt: The simple white t-shirt keeps the look clean and minimal, allowing the plaid shirt to stand out.

To add more flair to this look, consider accessorizing with a pair of chunky sneakers and a beanie for a street style edge. Avoid over-accessorizing as the outfit is already quite bold.

Pink and Green Combo

This playful and casual outfit features an oversized pink t-shirt paired with dark green joggers and black and white sneakers. It's a fun and relaxed look that's perfect for a casual day out.

• Oversized Pink T-Shirt: The t-shirt adds a pop of color and a playful touch to the outfit. Its loose fit makes it comfortable and easy to wear.
• Dark Green Joggers: The joggers provide a relaxed and sporty vibe, balancing the bright pink of the t-shirt.
• Black and White Sneakers: The sneakers add a touch of casual style, keeping the look cohesive and comfortable.

To elevate this look, consider adding a denim jacket for an extra layer of style. Avoid adding too many colors as the pink and green combination is already bold.

Neutral Tones

This chic and relaxed outfit features a beige oversized t-shirt paired with white wide-leg pants and a plaid shirt tied around the waist. It's a stylish and comfortable look that's perfect for a casual day.

• Beige Oversized T-Shirt: The t-shirt adds a neutral base and a relaxed vibe to the outfit. Its loose fit makes it comfortable and easy to wear.
• White Wide-Leg Pants: The pants provide a clean and polished look, balancing the casualness of the t-shirt.
• Plaid Shirt: Tied around the waist, the plaid shirt adds a touch of pattern and breaks up the monotony of the neutral tones.

To add more style to this look, consider accessorizing with a pair of chunky sneakers and a baseball cap for a casual chic vibe. Avoid over-accessorizing as the neutral tones and plaid shirt already provide enough visual interest.

Pink and Black Contrast

This vibrant outfit features a bold combination of pink and black, perfect for making a statement in the streets of Nyc or La. The pink flannel shirt layered over a pastel pink sweatshirt creates a striking contrast against the white pants, resulting in a stylish and edgy look.

• Pink Flannel Shirt: The oversized flannel shirt in a bold pink and black check pattern adds a playful yet edgy touch to the outfit. Its relaxed fit makes it comfortable and trendy.
• Pastel Pink Sweatshirt: Layered underneath, the pastel pink sweatshirt provides a softer contrast to the bright flannel shirt. It's cozy and adds warmth for the fall season.
• White Pants: The wide-leg white pants balance the boldness of the pink, creating a clean and modern silhouette.

To enhance this look, consider adding a pair of chunky sneakers for a casual comfy vibe. Avoid over-accessorizing, as the bold colors and patterns already provide plenty of visual interest.

Black Athleisure

This all-black athleisure outfit is perfect for a sleek and stylish street style look. The oversized black sweatshirt paired with black joggers and chunky black sneakers creates a cohesive and modern ensemble ideal for a casual day out in Chicago or Ny.

• Oversized Black Sweatshirt: The sweatshirt features a slightly faded black print, adding texture and depth to the outfit. Its oversized fit makes it comfortable and stylish.
• Black Joggers: The joggers are relaxed and comfortable, perfect for a sporty and laid-back look. They balance the bulkiness of the sweatshirt.
• Chunky Black Sneakers: The chunky sneakers add a modern and trendy touch, completing the all-black ensemble.

To elevate this look, consider adding a black oversized blazer for an extra layer of style. Avoid adding bold accessories, as the simplicity of the outfit is part of its charm.

Monochrome Patchwork

This unique outfit combines different textures and patterns to create a standout look. The black and white patchwork sweater paired with a tiered white skirt is both playful and stylish, perfect for a day out in Europe or Japan.

• Patchwork Sweater: The sweater features a mix of different black and white patterns, adding a unique and eclectic touch. Its oversized fit makes it comfortable and trendy.
• Tiered White Skirt: The skirt adds a feminine touch with its ruffled tiers, creating a contrast to the edgy sweater.
• White Sneakers: The white sneakers keep the look casual and comfortable, perfect for a day of exploring.

To add more depth to this look, consider accessorizing with a pair of chunky sneakers and a beret for a more polished vibe. Avoid adding too many colors, as the monochrome palette is part of the outfit's appeal.

Cozy Plaid Layers

This cozy and stylish outfit features a plaid shacket layered over a hoodie, paired with white joggers and tan boots. It's the perfect look for a relaxed day out in Cali or Ny.

• Plaid Shacket: The shacket combines the structure of a jacket with the softness of a shirt, making it a versatile layering piece. Its plaid pattern adds a touch of classic style.
• Gray Hoodie: Layered underneath, the hoodie adds warmth and a casual vibe to the outfit. Its neutral color keeps the look cohesive.
• White Joggers: The joggers are comfortable and relaxed, balancing the structured shacket and adding a sporty element.
• Tan Boots: The tan boots add a touch of warmth and complete the cozy look.

To elevate this outfit, consider adding a matching plaid scarf for extra warmth. Avoid heavy accessories, as the layered look already provides enough visual interest.

Bold Pink Blazer

This bold and sophisticated outfit features a hot pink oversized blazer paired with a white crop top and matching white skirt. It's a striking look that's perfect for a day in the office or a night out in Hong Kong or Nyc.

• Pink Oversized Blazer: The blazer is a statement piece with its bright pink color and oversized fit. It adds a bold and modern touch to the outfit.
• White Crop Top: The crop top provides a clean and minimal base, allowing the blazer to take center stage.
• White Skirt: The matching skirt keeps the look cohesive and polished, creating a streamlined silhouette.

To enhance this look, consider adding a pair of chunky sandals for a modern touch. Avoid over-accessorizing, as the bold pink blazer is already a standout piece.

Fall fashion offers endless possibilities for creating unique and stylish outfits. By layering and combining different pieces, you can achieve looks that are both practical and fashionable. Whether you're inspired by the streets of Nyc or the cozy vibes of Chicago, there's a fall outfit out there for everyone. Share your favorite fall looks in the comments below and let's keep the fashion conversation going!