10 Fall to Winter Fashion Looks to Inspire Your Street Style Obsession

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Patrick Porto

Summer’s lease hath all too short a date. The west wind starts to bring the long-hoped coolness back to the northern hemisphere. Although fall is still several weeks away, it’s never too early to think about what to wear on the days when we can mix and match. Are you tired of digging out your hand-me-downs and resuming your last autumn ensemble? Before hurrying to shop, let’s see what inspiration we can draw from street style in Scott Schuman’s camera.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Fashion is a loop


Vintage can never go out of date. A foolproof styling in the 60s is to opt for monochrome and plain items; they will look after themselves! Instead of going with suit pants, choose a pair of jeans to lend instant casual appeal to your outfit. Stepping into these Piedàterre shoes is like stepping into a time machine returning to the '60s. Simple embellishments, like sunglasses and a Beanie cap, serve more than accentuating a retro outfit without feeling too overdone.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Fallen leaves and burnt orange, a match made in heaven


Knit cardigans are definitely a winter wardrobe essential in the transitional season. Pair the burnt orange cardigan with a plaid pleated skirt and go for the schoolgirl vibes. A pair of mid-calf boots with an animal print can avoid looking too preppy. Keep it monochrome with a corresponding hue and let the patterns add an extra bit of complexity and oomph to the overall aesthetic.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • A smiley face is the most natural embellishment


Swap for a knit bodycon one-piece dress to ease the costumey sense when the temperature dips. Crab a sweater to keep you snug in the days with chilly mornings and warm afternoons and make it an accessory whenever your moods strike. Slip on a pair of sandals to feel the coolness of fall and show off your cute pedi.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Paris in the rain


Embrace a woolen blazer if you are not a big fan of burrowing into oversized fuzzy sweaters. And it can be a shelter in sudden rain (but an umbrella can do better). Finish your smart look with skinny dark jeans and a pair of mid-calf boots. You can never get enough of the jeans-boots combo.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Keep it monochrome with a corresponding hue


A trench coat is always an evergreen staple in warm fall. Opt for a khaki trench coat and straight-leg trousers in the same color family for a perfect fall ensemble. Let your accessories stand out as the main attraction in your outfit. A silk scarf or a chain strap will be a BFF.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Balance dark clothing look with beige jeans


A pair of white or beige mom jeans can solve all your problems of what to pair with dark overcoats. The light shades can balance the demure atmosphere and breathe new life into your look. Square-toe ankle boots with heirloom quality are a more wearable choice for year-round styling. Apart from summer dresses, they can go well with your mom jeans for a classic Parisian look.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • It’s OK to stay in your comfort zone of black and white


Don't underestimate the power of a black-and-white outfit. Embrace the clashing of billowing materials with tight-fitting garments to avoid dullness. Finish the look with a color-blocking scarf to keep you warm while going bare-legged.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Let colors burst


Don’t skimp out on mixed colors. Pick the motley items in the plain design and keep the accessories fairly minimal. It can be an easy-to-master but breathtaking look just like black-and-white. Being not total master classes, these varicolored babies are stylish enough to make a statement in your closet.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Head-to-toe black look: je ne sais quoi


Total black outfits can showcase your unique sense of style with the right items. Pair padded puffers with long swing dresses to complete a fab layering fashion. Accentuate your simple outfit with metallic ornaments to add up to just the right amount of polish.

a young woman wearing steet style inspired look for fall/winter and posing on a street
Photo: Scott Schuman/ Instagram: @thesartorialist

  • Never too late to invest in a reversible puffer


Wear your thermal layers and wrap them up in a reversible puffer against the frigid air. Leave it unbuttoned and show off the details inside. You’d better choose a longer bottom to save yourself from hypothermia.

Summarizing...


As the vibrant leaves fade into the cool embrace of winter, your fashion journey continues to evolve. These 10 captivating fall-to-winter ensembles have woven a tale of style, seamlessly transitioning from the warmth of fall to winter colors to the chic layers of winter's embrace. Whether it's the cozy knit scarves or the bold statement coats, these looks have whispered tales of sartorial finesse and unspoken elegance.
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