Sidewalk Chic: Trendsetters’ Advance Look at Fall/Winter 2025/2026’s Top Dresses

In the chilly months, foregoing dresses is not an option; instead, embrace these: trends featuring lengthy maxis, comfy knitwear, and strategic layering guarantee warmth throughout the autumn and winter seasons. During the most recent Fashion Weeks, street-style stars and celebrated influencers have already showcased the key dresses for the season, leading us to compile the most stunning ensembles and guide you toward replicating these winning combinations this fall and winter.

Knitted dress + chunky boots

This pairing emerges as one of the most stylish and functional choices, fitting for both celebratory occasions and daily urban living. To draw admiring looks, opt for a knitted dress in a vibrant hue – a lively orange is particularly fashionable right now. For a more subdued approach, a gray dress coupled with substantial boots is a great pick.

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Jacket dress + high heels

The actress Phoebe Tonkin was sighted on the streets of Paris sporting an edgy appearance, featuring a leather jacket styled as a minidress. Securing the “dress” with a belt around the lower waist, she confirmed the prevailing low-rise trend. However, mini lengths are not the only style setters this season: a dress-jacket in maxi length and a sophisticated brown shade was spotted on another style enthusiast, who accessorized it with a slender black scarf and black heeled boots. Top this off with an oversized gray wool coat or a faux fur coat, and you’re perfectly styled for the winter season.

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Translucent dress + suede boots

“Sheer” dresses are now recognized as both versatile and essential in one’s wardrobe, akin to the classic little black dress. On days filled with sunlight, simply adding a leather jacket and ankle boots might be adequate for complementing a translucent dress. Alternatively, in freezing conditions, adopt the principle of layering, and wear pants underneath.

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Black maxi dress + pointed boots

Generally, wearing a black dress maintains its relevance each season. This autumn-winter 2025/2026, we are spoiled for choice, ranging from knit to lace and evening varieties. A simple, flowing maxi dress is among the coziest options for daily wear, gaining extra sophistication with pointed boots.

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Lingerie style dress + chunky boots

Mirroring the sheer dress, the lingerie-style dress becomes a fresh essential, adaptable with various items to suit diverse feelings. Consider a contrasting approach, pairing a delicate pink satin midi dress featuring lace trim with a black bomber jacket and chunky, wide-top boots. The outcome? A daring style where each piece smoothly enhances the others.

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