Winter styling is the complete antithesis to other seasons, as the cold weather takes over we veer towards deeper hues, jewel tones and steadfast items that have met the style and warm criteria over the years. However, you aren't alone if you too lack inspiration when outfits are swallowed whole by oversized coats. This time of year is all about layering and outfit combinations. During the winter, I go for black dress and boots ensembles more than anything else. Within one fall sweep, you have a head-to-toe outfit that's practical, looks considered (in an effortless way) and stylish. It's a combination that always looks chic, understated and bears a chic Scandi lilt (Scandinavian women are experts at wearing monochrome outfits, after all).
I've never met someone who didn't love a LBD and although they're best associated with eveningwear, there are myriad of ways to style black dresses which transcend the after-dark realm. Simply pairing them with boots, instantly makes them daytime-appropriate. When it comes to choosing which dresses to style with boots, the options span from long-sleeved dresses to bodycon numbers and even minis. Jumper dresses are also a very popular winter addition, in various cuts — from high neck to raglan styles you can cinched in at the waist (there's more on that later).
During the winter, there's also an opportunity to reinvent evening gowns with hardened footwear and structured coats. It's fair to say, everyone could benefit from a black dress in their arsenal. Keep on reading for six-inspired black dress and boot looks to carry you through winter and beyond.
1. Suede Dress + Suede Blazer + Riding Boots
Style Notes: For a monochromatic take on equestrian-inspired style, pair a sleek suede dress with a matching suede blazer. This texture-rich combination creates a polished look, while riding boots add a touch of timeless sophistication. Opt for knee-high riding boots in leather or suede to maintain the tonal balance, and finish with understated accessories like a structured shoulder bag or minimal gold jewellery. Perfect for a day-to-night transition, this outfit is equal parts chic and versatile.
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Zara is always my first stop when I'm looking for those on-trend pieces.
As the residential millennial I will never tire of adding Topshop into my wardrobe. This blazer is so chic and I am in love with the deep chocolate colour.
These would look so good with some baggy jeans tucked in and an oversized coat.
Small but might! Bowling bags are a literal Mary Poppins-esq holdall.
2. Bodycon Dress + Boxy Leather Jacket + Knee-High Boots
Style Notes: Add a boxy leather jacket to a bodycon dress to juxtapose an androgynous and feminine silhouette. A look you can easily take into after-dark territory.
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Whistles is renown for its leather jackets––the quality is exceptional.
This comes in sizes XXS-4XL.
You can never go wrong with Missoma jewels.
Celebrities, fashion editors and influencers all rely on Paris Texas boots.
3. Full Skirted Maxi Dress + Pointed Heeled Boots
Style Notes: Take note from Marina and pair your flouncy frock with a cropped jumper over the top. Layer with dainty accessories and prop this look up with sleek heeled boots.
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Whip off the jumper and add heels for evening.
This comes in so many colours.
The most effortless everyday chain.
These also come in chocolate brown suede.
4. Roll Neck Dress + Belt + Slouchy Boots
Style Notes: If you want to instantly overhaul a look, pay attention to accessories. Add gold jewellery and a buckled belt to a sleek black dress and you've instantly elevated an otherwise simple outfit.
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The wool style also makes it so cosy.
Love the contrast stitch on this one.
These could easily pass as a vintage find.
This slouchy style will sell out, fast.
5. Jumper Dress + Chunky Ankle Boots
Style Notes: Make like Lois and pair an oversized jumper dress with chunky Chelsea boots and a hands-free crossbody bag. Although we're in the depths of winter, sunny days sometimes make an appearance in London, so add a pair of sunglasses to tie the look together.
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The type of dress that will always work hard in your wardrobe. Wear it slouchy, or belt it at the waist.
Cos' crossbody bag is one of its bestselling items. It's available in so many colourways for 2024, but tan never fails.
I love wearing sunglasses in the winter, it adds a little mystery to your whole look.
Chelsea boots come in many different forms. Not only do lug sole platforms have an androgynous element, but they're also practical for the (dare I say it) snow.
6. Mini Dress + Maxi Coat + Over-The-Knee Boots
Style Notes: You needn't leave mini dresses behind for the cooler months. For winter, add a layer of warmth layer––there isn't a more classic style than a sleek maxi coat. For extra warmth (and to tick off Chloé's key boot trend), try out an over-the-knee style.
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The Frankie Shop style is the key silhouette.
Mini dresses are still proving popular as we transition into winter. They're very apt for the upcoming party season, too.
So chic.
They also come in brown or navy, but you can't go wrong with black.
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