Though summer seems to still be clinging on, soon enough the cooler autumn days will set in. When this happens, temperatures won’t quite reach the warmth required to go without and 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 eight foolproof jackets to go with dresses—a formidable outfit combination that’ll see you through autumn 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: Busy prints can be difficult to style. Instead, follow Franny Fyne’s lead by wearing an intricate pattern alongside a pale-toned jacket.
This soft hue is a nice contrast to the bold dress.
Shirt dresses are so flattering.
This feels like an authentic cowboy boot.
Style Notes: A belted jacket will create a flattering silhouette when paired with just about any dress, but it will look particularly modern alongside a bright mini and ankle boots.
You’ll never run out of ways to wear this jacket.
Bold red is trending.
When you’re not wearing dresses, style these boots with jeans.
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 a must-buy for spring, 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.
Fact: Charles & Keith makes the best designer-looking handbags.
Style Notes: A blazer is a seasonless wardrobe staple that can be worn all year round. We suggest matching an oversize iteration alongside a minidress and ankle boots for a quick and chic autumnal look.
Every good wardrobe includes an oversized blazer.
A dress you can wear all year round.
There’s something so chic about white boots, and this & Other Stories pair is no exception.
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 jacket as opposed to the usual jeans-and-shirt combination.
Plaid styles are forever in style.
There’s so many details to love.
The shoes of the moment.
Style Notes: 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 did.
Size up for a more relaxed fit.
This is an ideal layering piece.
This dark blue shade is a solid choice.
Style Notes: If anyone knows how to dress down fancy pieces, it’s Ada Oguntodu, and this outfit is prime example. Note how she balances out her thigh-high split with an androgynous bomber jacket and a pair of chunky trainers. Masterful.
Bomber jackets are a modern staple.
Dress it up for fancy dos, down for elevated everyday wear.
Comfort guaranteed.
Style Notes: With social calendars filling up, sequins are starting to land in our favourite shopping haunts in preparation. Pair mini hemlines with a cropped jacket like Babba Rivera did here.
We’re not only into oversized blazers—this cropped iteration is just as sleek.
When you want to have a good time, this is the dress to reach for.
These versatile slingbacks could be styled with so many outfits.
This post was originally published at an earlier time and has since been updated.
Next up: The Autumn/Winter 2023 Fashion Trends That Really Matter
