Not All Dresses and Jackets Go Together, But These 8 Timeless Combinations Work

September 06, 2020 at 06:09AM

Summer might be close to becoming a distant memory, but we’re not forgoing dresses just yet (if at all). With temperatures swiftly plummeting, however, 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.

Fret not, though, for we’ve found eight foolproof jackets to go with dresses. 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.

Style Notes: A belted jacket will create a flattering silhouette when paired with just about any dress, but looks particularly modern alongside a bright mini and ankle boots. 

Style Notes: The ’80s might be dominating the fashion scene this season, but that doesn’t mean the ’70s have been completely overlooked. Suede fringed jackets are a must-buy for autumn and winter, and cream linen is the perfect accompaniment. 

Style Notes: A blazer is a seasonless wardrobe staple that can be worn all year round. We suggest matching an oversize iteration alongside a mini dress and ankle boots for autumn. 

Style Notes: Traditional checks can be difficult to style. Instead, follow Michelle Driscoll’s lead by wearing a modern, colourful check alongside a neutral-toned blazer. 


Style Notes: One of the easiest fabric pairings out there is plaid and denim, and we love how Erika Boldrin has given it an elegant spin in the form of a dress and blazer as opposed to the usual jeans-and-shirt combination. 

Style Notes: While we’re on the subject, slip dresses are still all the rage right now. When you’re not at weddings, we recommend wearing them with a top underneath. Then give it an edgy overhaul with a leather biker just like Scandi style guru Jeanette Madsen. 

Style Notes: If anyone knows how to dress down fancy pieces, it’s Ada Oguntodu, and this outfit is no exception. Note how she balances out her sexy thigh-high split with an androgynous bomber jacket and a pair of chunky trainers. Masterful. 

Style Notes: As we inch ever closer to party season, we can no longer ignore the floods of sequins that are starting to land in our favourite shopping haunts. Echo mini hemlines with a cropped jacket, like Babba Rivera. 

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

Next up, the biggest S/S 20 fashion trends you need to know. 

Author Maxine Eggenberger | Whowhatwear
Selected by CWC

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