A woman in a stylish gray Fashion People Are Loving These Street Wear Style dress with cut-out shoulders stands by white columns. She holds a coat and wears transparent heels, looking directly at the camera.


The Dress Edit

Fashion People Are Loving These Street Wear Style Dresses For Fall

Whether you’re heading to a low-key brunch, a casual dinner date, a fashionable event, or something in between, these streetwear-style dresses are everything you need to look and feel your most stylish to date. From chic, long-sleeved knit silhouettes to edgy denim ones, you’ll want to be spotted in every single one of the dresses in our specially selected edit. The best part? These dresses are not only right on trend, they’re also seriously versatile and ideal for fall weather. Therefore, no matter the occasion, you’ll find your dream dresses for the season ahead await just a scroll away. Our advice? Add your favorites to your cart soon. These sought-after silhouettes won’t be around for long!

A woman in a Fashion People Are Loving These Street Wear Style Dresses For Fall walks under a bridge, her hair obscuring her face as sunlight casts sharp shadows around her.

@chloe / Instagram

A woman in a dark, patterned "Fashion People Are Loving These Street Wear Style Dresses For Fall" mini dress with long, flared sleeves poses confidently against a textured wall in a rustic setting.

Charo Ruiz

Street Wear Style Dresses That Go With Boots

Since boots are the only shoes we want to wear in fall weather, we’re always on the lookout for street wear dresses that look amazing with our go-to shoes. This year, we’re feeling particularly spoiled. Pretty much every dress on our list looks even more impressive with the right pair of boots! Our top recommendations? Let’s start with the Timothee dress by Song Of Style. Firstly, trust us when we say you’ll be reaching for this endlessly versatile dress on repeat all season long. Secondly, whilst you can definitely dress it up with heels for events, it looks undeniably cool with knee-high boots. Style yours with a timeless, heeled black or brown pair and feel instantly put together. We’re calling it, this is the must-have dress for fall 2023.


Meanwhile, when the event calls for a shorter hemline, we’ll be slipping into the Outlaw mini dress by Show Me Your Mumu. It’s the ultimate little black day dress for low-key plans. What’s more,  we’re obsessed with the plunge V-neckline, flattering belted waist, and corduroy fabric which also happens to be perfect for the cooler fall weather. Add this dress to your lineup, style it with heeled black booties, and never be stuck for a classically cool outfit ever again!

Shop more streetwear dresses selected and reviewed by our expert fashion buyers and stylists

  • MAX MARA Maremar Sleeveless Jersey Sheath Dress

  • JW ANDERSON Asymmetric Denim Midi Dress

  • ANTHROPOLOGIE V-Neck Sequin Deco Swing Dress

  • FREE PEOPLE Cypress Lace Maxi Dress

  • CEILONIA Fraser Dress

  • SHONA JOY Hele Ruched Panelled Midi Dress

  • AREA Studded Polka Dot Leather Dress

  • GIAMBATTISTA VALLI Bow-embellished Cotton-poplin Maxi Dress



Street Wear Style Dresses From Fall To Winter

Looking to invest in street wear style dresses that’ll see you stylishly through the rest of this year and beyond? You’ve come to the right place. Firstly, we recommend the silk-blend midi dress by Joseph. With a chic turtle neckline, long sleeves, and a mid-length skirt, this sweater-style dress is both warm and timelessly stylish. Pair yours with knee boots and subtle gold jewelry to nail the quiet luxury trend for fall. Then, simply add simple outerwear for the winter months.


Meanwhile, we’re all for versatility when it comes to purchasing a new dress. That way, you can wear it throughout multiple seasons by simply switching up your footwear and adding or taking away layers. For example, the Butterfly Babe lace maxi dress by Free People is the ultimate transitional piece. Firstly, we adore the floral butterfly print, short sleeves, and maxi-length hemline. Secondly, this dress goes just as well with flats and sneakers as it does with heels and boots. So, style it with boots for an adorable yet edgy fall look. Then, add gorgeous knitwear or a coat over top when temperatures really begin to drop. In this super pretty and versatile dress, you’ll look stunning and stylish either way!


Shop All Streetwear Style Dresses

A woman models an elegant cream long-sleeve dress with a belted waist and flowing skirt against a textured beige background, embodying a streetwear style that adds a dynamic flair to the Fashion People Are Loving These Street Wear Style Dresses For Fall.

Palmer Harding

A young woman with blonde hair wearing a Fashion People Are Loving These Street Wear Style dress stands outdoors on a sunny day, with a background featuring green grass and a residential building.


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