Posted on: October 31, 2023 Posted by: Comments: 0

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.

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

This soft hue is a nice contrast to the bold dress. 

A sweet addition to any outfit.

Keep wearing billowy dresses in the first weeks of autumn.

A timeless staple.

The perfect in-between season shoe.

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.

You’ll never run out of ways to wear this jacket.

Trust me, you’ll have this piece forever.

You can always rely on The Row for elevated footwear.

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. 

The perfect balance between statement and subtle.

This classic style will long have a place in your wardrobe. 

A pretty ring never goes amiss. This style would make for the perfect gift, too. 

Fact: Aspinal of London bags never date. 

Comfort guaranteed.

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. 

We’re not only into slouchy blazers—this cropped iteration is just as sleek.

A dress you can layer and wear all year round.

A suave (and reasonably priced) iteration of the bag we all know and love.

These versatile boots could be styled with so many outfits.

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. 

Size up for a more relaxed fit.

Everyone needs a dress like this in their wardrobe.

The ideal hue for autumn.

A piece you’ll wear and love forever.

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. 

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