It's the fail-safewinter outfit formula that we all turn to every year:dresses and boots. Comfortable, practical and understatedly cool, this combination never lets you down in the depths of the cold winter months, when you're juggling the desire to stay warm without compromising on style.
But like all good things, it can be difficult to keep it feeling exciting and fresh, especially if find one pairing that you turn to time and time again. Luckily, this season our favourite tastemakers are providing plenty of inspiration for different boot and dress combinations that look effortless, sleek and very 2024.
(Image credit: @claudia_berresford)
It seems like this year, there's a plethora of boot styles to choose from. Whileknee-highs are undoubtedly the silhouette of the season, chunky boots remain a top go-to among the fashion set (especially if you get your hands on The Row's cult pair). And then there are the classics: riding boots and simpleblack ankle boots will always serve you well. Paired with chunky knit dresses or slick, figure-hugging maxis, these boots can help adapt a simple dress to any situation. Scroll on to discover 12 of our favourite takes on the popular outfit.
1. MAXI DRESS + SUEDE BOOTS
(Image credit: @rosiehw)
Style Notes:An all-black ensemble always looks chic, but Rosie takes it up a notch by pairing a figure-hugging maxi dress with pointed-toe boots.
Shop the Look:
Raey
Round-Neck Cotton-Blend Jersey Maxi Dress
Simple, but so effective.
Jones Bootmaker
Suede Stiletto Heel Knee High Boots
These wouldelevate so many different outfits.
Toteme
T-Lock Large Grained-Leather Cross-Body Bag
I love the two handles on this incredibly chic, minimalist bag.
2. SWEATER DRESS + BIKER BOOTS
(Image credit: @annabelrosendahl)
Style Notes: How cosy does this look? Practical biker boots make this ideal for a day of running around town, but you could easily swap in heeled styles for an evening event.
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H&M
Rib-Knit Dress
Effortlessly cool, this is a great alternative to the pricier style Annabel is wearing.
H&M
Biker Boots
The buckle detail gives these biker boots just the right amount of edge.
Arket
Ribbed Merino Beanie
The winter essential.
3. MINI DRESS + POLKA DOT TIGHTS +KNEE-HIGH BOOTS
(Image credit: @chrissyford)
Style Notes: Patterned tights are making a comeback this season, and Chrissy shows how to style them in such a sleek way.
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COS
Printed Roll-Neck Mini Dress
The geometric print and high neck gives this mini dress a Sixties feel.
Anthropologie
Sneaky Fox Clara Sheer Polka Dot Tights
A subtle scattering of polka dots.
Toteme
The Slim Leather and Suede Knee-High Boots
Aren't we all thrilled that kitten heels are trending right now?
H&M
Coated Trenchcoat
This is such a standout coat—and it goes up to a 4XL.
4. MAXI JUMPER DRESS + CHUNKY SOLE BOOTS
(Image credit: @isabellecoheen)
Style Notes:Proof that chunky sole, flat boots can look extremely sophisticated.
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Autograph
Merino Wool Rich Knitted Dress With Cashmere
This colour is so versatile.
Anthropologie
The Petra Mini Drop Earrings
Such a great dupe ofthose viral earrings.
The Row
Zip-Front Leather Ankle Boots
These cult boots always sell out—grab them while you can.
COS
Slouchy Shoulder Bag
COS always delivers on sleek, minimalist accessories.
5.SPARKLYDRESS + BLAZER + TALL BOOTS
(Image credit: @sasha.mei)
Style Notes:This is such a great look for festive events—and tall boots are the ideal party shoe for dreary December nights.
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Rixo
Zuri
This is the ultimate party dress—just imagine how this looks when it catches the light?
& Other Stories
Satin-Detailed Wool Blazer
Bring a tuxedo touch to this party outfit.
Reformation
Nylah Nappa Knee Boot
These would work equally well with day looks.
6. SHIRT DRESS + TRENCH COAT + ANKLE BOOTS
(Image credit: @cocobassey)
Style Notes:If you love the silhouette of a shirt dress, you can easily bring it into the winter months by styling it with a classic trench coat and slick ankle boots.
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H&M
Tie-Belt Shirt Dress
The crinkled pleats and wide cuffs make this look so much more expensive than it's pricetag.
Jigsaw
Technical Shell Mac in Black
I love the dramatic collar on this trench—and the fact it's actually water-repellant.
Toteme
The City Leather Ankle Boot
The Chelsea boot and Western boot crossover I didn't know I needed until now.
7. SWEATER DRESS + RIDING BOOTS
(Image credit: @cassklatzkow)
Style Notes: A simple monochromatic look that's so effective—and demonstrates exactly why riding boots will always be in style.
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Free People
Melanie Sweater Tunic
White dresses always look particularly chic in the winter months when contrasted with black tights.
Jigsaw
Riding Boot in Black
These boots are up for whatever you have planned.
Arket
Wool Pea Coat
A pea coat is a style that always looks effortlessly polished.
8. RIBBED KNIT DRESS + COLOURFUL BOOTS
(Image credit: @babba)
Style Notes:The electric blue boots really make this look pop, and add a fun touch to an otherwise very proper outfit.
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Mango
Perkins-Neck Ribbed Dress
This dress could easily go from day to night.
Topshop
Bowie Boot in Blue
A pop of colourthat would do their namesake proud.
H&M
Oversized Single-Breasted Blazer
The oversized fit makes it perfect for layering over a knit dress.
9. CABLE KNIT DRESS + PATENT LEATHER BOOTS
(Image credit: @anoukyve)
Style Notes:Simplify winter dressing by picking one colour and building your whole outfit around it. While black will always be a reliable go-to, brown is a softer, warmer option that looks impressively elegant.
Shop the Look:
Arket
Cable-Knit Wool Dress
A deliciously rich chocolate tone.
Saint Laurent
Vendome 110 Patent-Leather Boots
They're an investment, but they look so, so good.
Reformation
Medium Rosetta Shoulder Bag
The contrast of the brown suede with the patent leather would really make this look.
10. MIDI DRESS + COWBOY BOOTS
(Image credit: @juliesfi)
Style Notes:Cowboy boots keep coming back into fashion, and for good reason. They're understatedly cool, and bring an edgy touch to an otherwise soft, cosy look.
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Reformation
Ida Cashmere Sleeveless Sweater Dress
I love the silhouette of a sleeveless, turtleneck midi dress.
Paris Texas
Rosario Cowboy Boots
The embroidered motif give these an authentic Western look.
H&M
Coated Blazer
A leather blazer is an easy way to upgrade any outfit.
11. MINI DRESS + OVER-THE-KNEE BOOTS + LONG COAT
(Image credit: @dawn.tan)
Style Notes:Consider this a masterclass in playing with proportions. While the dress may be super short, the floor-sweeping coat and over-the-knee boots mean only a flash of skin is showing, making it a truly versatile outfit that could work for so many situations.
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Mango
Fitted Turtleneck Dress
Such a sleek base layer for so many possible looks.
Mint Velvet
Black Over the Knee Boots
I love the contrast of the sensual over-the-knee leg with the chunky riding boot sole.
Toteme
Signature Pressed Wool and Cashmere-Blend Coat
This coat wouldrefine any outfit.
12. PARTY DRESS + PATENT BOOTS
(Image credit: @_jeanettemadsen_)
Style Notes:I'm saving this for my New Year's Eve outfit inspo. The contrast of the dress and the high-shine patent leather knee-high boots is perfect for winter celebrations, and I'd add a leather trenchfor venturing outside.
Shop the Look:
Rixo
Vivi Velvet Mini Dress
The velvet and the crystal-embellished box at the bottom of the v-neckline make this such a perfect winter party dress.
Mango
Patent Leather-Effect Heeled Boots
These boots are calling out to be your next party plus one.
Toteme
Raglan-Sleeve Leather Coat
I cannot stop thinking about this coat—it's such a cool, minimalist take on the leather trench.
Next up:Fashion People Rely on This Classic Wardrobe Staple—21 of the Best For Winter
Explore More:
BootsStyle TipsKnee High BootsOver-The-Knee Boots
