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The holidays are over, unfortunately, and I’ve hung up all of my favorite sequin party dresses. And not only is the marathon of end-of-year celebrations officially over, the temperatures have finally started to drop, too. If you’re like me, you’re probably feeling the need for some serious style inspiration to spice up the winter doldrums right about now.
To avoid the classic midwinter wardrobe slump that is wearing the same sweater-and-jeans combo for weeks, I’ve searched for motivation to get dressed with a capital D to kick off 2024. Street style can be one of the most inspiring sources for me when I’m creating cute
winter-outfit mood boards. So below, I pulled together some of my favorite looks from Fashion Month, to help you breathe new life into your tired cold-weather wear.
Of course, there are plenty of coats, knits, and boots—the obvious must-haves—but I am leaning into a bit of the unconventional, as well. Leather and other textured fabrics are in no short supply on my checklist, while tailoring and midi skirts have become fashion’s new favorites, and mine too. When all else fails, the best basics with a twist make for easy outfit formulas that are foolproof. Think funky denim, colorful striped sweaters, and structured oversize outerwear that makes layering a breeze.
Below, 25 winter outfit ideas from some favorite street-style stars—to keep you inspired to really get Dressed, all season long.
1
Simple & Chic
All you need is a black coat, maxi skirt, and a great flat shoe to re-create this effortless ensemble. On colder days, we recommend adding tights and layering with an oversize cable knit sweater. Sling a designer bag to give it that extra dose of fashionable flair.
Vince Brushed Flannel Maxi Skirt
Vince Brushed Flannel Maxi Skirt
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Vince Venice Slingback Flat
Vince Venice Slingback Flat
2
Sporty Spice
For a modern spin on a gray day, mix warm tones like burgundy with mustards or khaki. A wrap jacket, utilitarian trousers, and a ball cap may seem like an unlikely pairing, but TyLynn Nguyen proves this quirky ensemble just works.
Belle & Bloom Eternal Flame Tie-Waist Wool-Blend Coat
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The Frankie Shop Maesa Pleated Wide-Leg Cargo Pants
The Frankie Shop Maesa Pleated Wide-Leg Cargo Pants
Frame + Ritz Paris Embroidered Suede Baseball Cap
Frame + Ritz Paris Embroidered Suede Baseball Cap
3
Simplicity City
Uncomplicated is the name of the game. A chunky, mélange knitted turtleneck, straight midi skirt, and black knee-high boots make for a truly effortless look that can be worn to the office or a dinner date. Top with your favorite coat and you’re good to go.
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Iris & Ink Charlie Merino Turtleneck Sweater
Iris & Ink Charlie Merino Turtleneck Sweater
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4
Layered Leather
What’s better than one leather jacket? Two leather jackets, obviously. On the runway, Mrs. Prada has given us permission to layer up on the good stuff. To pull off this look without a snag, be sure to choose something like a blazer that is more tailored and easier to wear under an oversize jacket.
Generation Love Milan Vegan Leather Blazer
Generation Love Milan Vegan Leather Blazer
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Miu Miu Quilted Leather Top-Handle Bag
5
The Knitty-Gritty
Knit sets are wardrobe game changers that make hectic mornings a breeze. We love this bold red to break up the winter blahs. Simply pair with your favorite tailored overcoat and an embossed knee-high boot for some chic texture play.
Misook Textural Stripe Mock-Neck Cable-Knit Tank Top
Misook Textural Stripe Mock-Neck Cable-Knit Tank Top
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Misook Textural Striped Knit Midi-Skirt
Misook Textural Striped Knit Midi-Skirt
Toteme The Slim 35 Croc-Effect Knee-High Boots
