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How to style a denim dress for winter like a fashion pro

Step one: Add boots.
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Edward Berthelot

If I were to ask you how to style a denim dress, your first thought might be with a cowboy hat at a Beyoncè concert. The staple boasts a distinctly Western aesthetic that its blue jean fellows (denim jackets, jeans, jorts, etc.) typically don’t. And because of that, denim dresses can sometimes feel a little harder to style or like they’re best suited to summer weather.

Don’t relegate it to the back of the closet once winter comes, though. Even your strapless minis can survive the season. Just accessorise well, and you can make any dress outfit feel sleek and elegant. For example, the addition of snakeskin knee-high boots (a Rihanna-approved pairing) will give your look a high-fashion vibe. A khaki trench coat and Mary Janes, meanwhile, inject a much-needed dose of polish into the casual style, while the addition of a suede jacket will introduce a bit of autumnal flavour.

Ahead, I’ve curated all the chicest and easiest ways to style a denim dress for the winter ahead. Here are all the best styling tips that will help you transform your jress (jean dress) for the season.

Glamour’s denim dress styling edit

Parsons Denim Midi Dress
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Paris Texas Stiletto snake-effect leather knee boots
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Ember Flared Bootcut Jeans
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With Snakeskin Shoes
PARIS FRANCE  SEPTEMBER 28 A guest wears a Ronny Kobo dress Versace sunglasses Alaia bag and Casadei boots outside the...
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If it’s good enough for Rihanna, it should be good enough for all of us. The makeup mogul loves a good denim-and-snakeskin moment, having worn the combo on dozens of occasions throughout the years. Test-drive the outfit idea for yourself by styling your own long-sleeve denim dress with a pair of knee-high faux-snakeskin boots, like the street-style look above.

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Parsons Denim Midi Dress

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Paris Texas Stiletto snake-effect leather knee boots

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Over Jeans
PARIS FRANCE  JANUARY 27 A guest wears navy blue denim jean long sleeve midi dress navy blue denim jean loose pants dark...
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Allow me to introduce the new and improved Canadian tuxedo. Layering a button-down midi, mini, or even maxidress over matching jeans is an undeniably stylish take on the classic all-denim look. Genuinely, who knew jeans could look so sophisticated? Go for heels or other dressy shoes that’ll also elevate the otherwise casual outfit.

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Mason Denim Midaxi Shirt Dress

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Ember Flared Bootcut Jeans

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With Leather Accessories
PARIS FRANCE  SEPTEMBER 30 Giulia Maenza wears a loose low ponytail shoulderlength light brown hair with a center part a...
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Dark-wash denim and leather is a love story for the ages. No matter how many years pass, the classic duo still plays just as well together as it did on the first day. You could always go with a leather jacket on top, or get the same effect with moto boots and a punk-inspired leather belt over an A-line dress.

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Amber Mini Denim Dress

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Maeve Leather Knee High Boots

Nipped at the Waist
NEW YORK NEW YORK  SEPTEMBER 10 A guest wears a blue denim jacket worn as a mini dress a mini skirt dark green knee high...
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One of the year’s most striking silhouettes involves a fitted waist with barrel sleeves. These design details are typically found in the blazer space, but you can’t go wrong with wearing an oversized one as a jean dress look. Black, blue, or indigo options work best for this, and we’d recommend wearing with knee-high boots and/or your best leggings. You can always add a pair of black shorts or a miniskirt underneath if you’re not sure about the length.

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ASOS DESIGN denim long sleeve fitted shirt mini dress in rinse

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Ivy Knee-High Boots

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Under a Trench Coat
COPENHAGEN DENMARK  AUGUST 08 A guest wears blue long maxi dress beige trench coat and brown bag outside the Marimekko...
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Trench coat season is in full swing, and the girlies are taking advantage. Part of their draw lies in their versatility – which means they look good styled with pretty much anything. And that certainly holds true for denim dresses (particularly maxi styles) and ballet flats. If you need an another layer, try a fitted cardigan for a touch of elegance.

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ALICE + OLIVIA Chassidy denim maxi shirt dress

Linnie Relaxed Fit Trench Coat

With Brown Boots and Gold Jewelry
PARIS FRANCE  SEPTEMBER 30 A guest wears gold pendant earrings a denim long sleeved mini dress and brown leather knee...
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Pretty much anything feels cozy when styled with chestnut boots and a pair of gold sparkly earrings. When paired with a denim minidress, the final result is straight out of a seasonal rom-com. As the weather gets chillier, add tights underneath or switch to a maxidress for extra warmth with the same effect.

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Era Lab-Grown Diamond Station Hoop Earrings

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ASOS DESIGN Candace premium pull on chisel toe knee boots in chocolate suede

With Suede Staples
COPENHAGEN DENMARK  JANUARY 28 A guest wears beige pants denim long dress brown suede jacket with tassels and sunglasses...
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For those of us who do vibe with the yee-haw look, a touch of suede – a jacket, boots, or a bag —with a denim midi-dress can amplify that energy in the best way. Finish with simple silver jewellery to keep the ensemble from looking too costumey.

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Steve Madden Luca Boot

With a Bandanna and Shield Sunnies
PARIS FRANCE  OCTOBER 06 A guest wears blue denim long sleeves dress with cut out details on the sides brown ballet flat...
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As a rule of thumb, I avoid aviator sunglasses any time I am dressed in denim. The combo can feel too costume-like, so I reach for a pair of trending shield sunnies instead. The posh addition, combined with a silk bandana and denim maxi, feels boho in a more fashion-forward way.

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Prada Eyewear Collection sunglasses

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TOTEME Striped silk crepe de chine scarf

Under a Shearling Vest
COPENHAGEN DENMARK  JANUARY 30 A guest wears denim dress beige vest sunglasses cow print bag and long brown boots...
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A denim shirtdress of any length looks chic (and oh-so cozy) with a boxy shearling vest. It’s a more subtle and modern way to embrace the Western aesthetic, especially when you add unexpected accessories like a pearl necklace or T-shirt underneath.

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Marlin Reversible Shearling Gilet

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Yolanda Pleated Denim Dress


This article was originally published on Glamour US.