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
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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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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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.
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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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.
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.
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.
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.
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.
This article was originally published on Glamour US.




















