Skip to main contentSkip to footer

When you purchase through links on our site, we may earn commission. Read our full commerce guidelines here.

Jackets to wear with dresses: the failsafe outfit combos

These are the outfit formulas we're wearing on rotation this season

Fashion week guest wearing leather bomber jacket with geometric midaxi © Getty
Orin Carlin
Content Writer
Updated: January 4, 2024
Share this:

Sign up to HELLO! Fashion for style tips, cultural insights, must-have items, and more

By entering your details, you are agreeing to HELLO! Magazine User Data Protection Policy. You can unsubscribe at any time. For more information, please click here.

The cold weather has got a little too comfortable for my liking – aren't we overdue a hit of heat? Irrespective of my personal preferences, it appears the chilly temps are something of a permanent fixture here in the UK. Head out without a jacket on, and you'll live to regret it. 

 For when swerving the extra layer is simply not an option, help is at hand.

Jackets and dresses can be curiously at odds – whether that's down to conflicting proportions or lengths. But there are a few key combos that hit the spot every single time and we're not here to gatekeep…

MORE: 10 ways to wear trainers with dresses

Fashion week guest wearing moto jacket with denim ruffle dress © Getty
Styling a jacket with a dress can actually be a bit of a minefield

How we chose:

Fashion week guest wearing short fitted denim jacket over mini dress © Getty
A shorter jacket that finishes at the same length as your mini dress can look really cohesive
  • Style and versatility: All our jacket picks feature a flattering silhouette and work harmoniously with the dress styles we've suggested. When combing through the internet's top fashion sites for the best styles, we made sure that each of our outfit combinations are either trend-relevant or timeless for maximum wearability. 
  • Price: Whether you're planning on splashing out or bagging a bargain, we've got a jacket in your price range. We've selected this season's best, ranging from high-street brands to luxe designer labels.
NYFW guest wearing white jacket with flowy printed maxi © Getty
Cropped, soft-silhouette jackets can work beautifully alongside flowy maxis

READ: How to style an oversized jumper and the best knits to shop this season

MORE: Best bomber jackets: 12 styles to amp up your outerwear collection

Hello! Fashion shares the best ways to style jackets with dresses:

Tweed jacket + Polo neck dress 

Outfit consisting of tweed khaki jacket, black polo neck dress and chunky loafers
Featuring Mango's Pocket Tweed Jacket in khaki

Tweed and bouclé jackets are having a moment right now, and I love the slightly utilitarian feel of Mango's multi-pocketed khaki version. Round necklines work really well layered over polo style knits, and this stretch-infused midi by French Connection feels super versatile. Top it off with chunky loafers - Tod's would be my preference if you're looking to invest - to offset the French-girl elegance of the jacket with a harder edge.

Pocket Tweed Jacket, £79.99, Mango; Babysoft Roll Neck Midi Dress, £85.00 £59.00, French Connection; Tod's Gomma Pesante Embellished Glossed-Leather Loafers, £690.00, Net-A-Porter 

Moto jacket + Slip dress

Outfit featuring moto jacket, green slip dress and trainers
Featuring H&M's Racer Jacket

I love the graphic impact of a moto jacket, and there are heaps of great affordable options out there right now. H&M's faux leather version feels wearable and cool, and I love the pairing of the black against the soft, slightly creamy hue, as opposed to super stark white. The shiny finish pairs well with a silky texture, and Hush's easy-breezy Alessandra slip won't break the bank. For a dose of casual cool, finish the look with sustainable sneaker label Saye's corn vegan napa Modelo '92s.

Racer Jacket, £49.99, H&M; Alessandra Slip Midi Dress, £89.00 £35.00, Hush; Modelo '92 - Garnet, £179.00, Saye

Boxy Western jacket + Denim dress

Outfit featuring fringed jacket, denim strapless dress, burgundy boots and gold statement earrings
Featuring Polo Ralph Lauren's Fringed Leather Jacket

Inject your wardrobe with a sense of movement and embrace fringing this season, as seen at the likes of Prada, Gucci and Burberry. This boxy silhouette by Polo Ralph Lauren would look great over denim if you're leaning into the cowboy aesthetic. For added interest, pair with independent label Rai Jewellery's opulent Arewa earrings and complete with a sharp boot - this brown croc print style by Everlane has really interesting heel curvature.

Polo Ralph Lauren Fringed Leather Jacket, £1,900.00, Net-A-Porter; Reformation Eugenia Strapless Stretch-Denim Midi Dress, £200.00, Selfridges; The Banana Heel Boot, £261.00, Everlane 

Belted blazer + Mini dress

Outfit consisting of grey belted blazer, leather mini dress, two-tone Mary Janes and silver waterfall crystal earrings
Featuring Cos' Belted Double-Breasted Wool Blazer

A relaxed-fit blazer and a spirited mini length is a match made in proportional heaven. I love the unfussy silhouette over a more form-fitting party piece, and Cos' slate grey jacket even features a delicate belt if you're wanting to create some gentle shape. Mango's faux leather strapless dress is timeless and minimalist, and I've fallen hard for Jimmy Choo's two-tone Mary Janes - ideal if you're after a more forgiving heel height. For a hint of glitz, Oliver Bonas' Angelique tassel earrings easily fit the bill. 

Belted Double-Breasted Wool Blazer, £155.00, Cos; Leather-Effect Strapless Dress, £49.99 £29.99, Mango; Angelique Glass Stone Tassel Drop Statement Earrings, £28.00, Oliver Bonas; Jimmy Choo Elisa 45 Glittered and Patent-Leather Mary Jane Pumps, £625.00, Net-A-Porter 

Shearling jacket + Neutral knit dress

Outfit consisting of shearling jacket, beige jersey dress, cream boots and gold T-bar necklace
Featuring Loewe's Shearling Jacket

The shearling jacket is a cold month classic, and Loewe's boxy version has a timeless quality. Cut from soft, sand-coloured lamb's leather, it would look beautiful as the focal point of a tonal look layered over Khaite's flattering Oron gown. Leaning into a neutral colour palette, Dear Frances' sleek cream boots would make for a worthwhile investment and finish with chic chain purveyor Tilly Sveaas' Short Gold Lariat necklace.

Loewe Shearling Jacket, £4,550.00, Net-A-Porter; Khaite Oron Gathered Stretch-Jersey Gown, £1,350.00, Net-A-Porter; Hetti Boot, £600.00, Dear Frances; Short Gold Lariat Necklace, £250.00, Tilly Sveaas

Why you should trust me:

Orin Carlin is Hello! Fashion’s SEO Content Writer. Promising to leave no stone unturned in the name of fashion and beauty journalism, she is the proud creator of our ‘Try The Trend’ series. With a particular interest in formula innovation, microtrends, royal and bridal beauty, perfume, rituals, treatments, fashion history and vintage icons, she can either be found interviewing major industry names (previous subjects include Georgia May Jagger, Mary Greenwell and Sam McKnight) or scouring the internet for must-have pieces. It's not just a job; it's a personal quest to unearth noteworthy pieces that resonate with style and beauty enthusiasts.

HELLO!'s selection is editorial and independently chosen – we only feature items our editors love and approve of. HELLO! may collect a share of sales or other compensation from the links on this page. To find out more visit our FAQ page.

More Hello! Fashion

See more