Not All Dresses and Jackets Go Together, But These 5 Timeless Combinations Work

The cooler months have settled in for the long haul and that calls for one thing: Outerwear. When this happens, temperatures won't quite reach the warmth required to go without an extra layer, and we recommend wearing yours with one item in particular: a jacket. You might not think it, but dresses and jackets are notoriously difficult to style together. With varying lengths, it doesn't take much, perhaps an inch in either direction, to throw off your look. And of course, this isn't what you want or deserve.

Fret not, though, for we've found five foolproof jackets to go with dresses—a formidable outfit combination that'll see you through the season and beyond. Whether your style errs on the casual side or you prefer a more polished way of dressing, our fashion friends have your next dress-and-jacket outfit sorted. So what are you waiting for? Give your jeans and jumpers a break, and keep scrolling to see and shop our favourite jackets to wear with dresses.

1. Relaxed Biker Jacket + Maxi Dress

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(Image credit: @bubblyaquarius)

Style Notes: Follow Rachael's lead by wearing a slouched black biker jacket alongside a pale-toned dress.

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2. Belted Blazer + Maxi Dress

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(Image credit: @brittanybathgate)

Style Notes: A belted jacket will create a flattering silhouette when paired with just about any dress, but it will look particularly modern alongside 2023's longline hem.

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3. Tan Suede Jacket + Cream Dress

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(Image credit: @monikh)

Style Notes: The '90s might be dominating the fashion scene this season, but that doesn't mean the '70s have been completely overlooked. Suede fringed jackets are timeless and cream linen is the perfect accompaniment. 

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4. BLAZER + PLEATED MIDI

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(Image credit: @_jessicaskye)

Style Notes: A blazer is a seasonless wardrobe staple that can be worn all year round. We suggest matching a streamlined and cropped iteration alongside a midi dress and ankle boots for a quick and chic autumnal look. 

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5. Brown Leather Jacket + Knitted Dress

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(Image credit: @sylviemus_)

Style Notes: Knitted dresses are all the rage right now. Give it an edgy overhaul with a longline leather jacket just like Parisian style guru Sylvie did. 

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Next Up: The 9 Most Expensive-Looking Pieces on the High Street This Week

This post was originally published at an earlier time and has since been updated. 

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over twelve years of experience in fashion journalism. She been creating engaging and elevated style content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories, and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, works closely with influencer talent on content initiatives, represents the brand at industry events, and regularly contributes to social media. Previously, Maxine appeared on TV in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o. 


Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship, she was offered a position on the Look magazine fashion desk. She accepted, leaving university a year early in the process. She went on to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion writer along the way. She later served as Look’s acting Editor in Chief before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others. Maxine works remotely from her countryside home near Edinburgh.