These 25 Winter Outfits Make Getting Dressed for the Cold Easy (2024)

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (1)

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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.

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.

H&M Double-Breasted Wool-Blend Coat

$279 at H&M

Vince Brushed Flannel Maxi Skirt

$395 at Neiman Marcus $395 at Nordstrom $395 at Bloomingdale's

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Vince Venice Slingback Flat

$330 at Nordstrom $295 at Zappos $330 at Neiman Marcus

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

$260 at Nordstrom $130 at Macy's

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The Frankie Shop Maesa Pleated Wide-Leg Cargo Pants

$225 at NET-A-PORTER

Frame + Ritz Paris Embroidered Suede Baseball Cap

$300 at NET-A-PORTER

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

$177 at The Outnet

Mango Ribbed Midi Skirt

Now 50% Off

$30 at Mango

Aeyde Teresa Leather Knee Boots

$745 at NET-A-PORTER

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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

$365 at Saks Fifth Avenue $365 at Bloomingdale's

Vince Leather Buttoned Shirt

$695 at Saks Fifth Avenue $695 at Nordstrom

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Miu Miu Quilted Leather Top-Handle Bag

$3,000 at Bergdorf Goodman

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

$228 at Neiman Marcus

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Misook Textural Striped Knit Midi-Skirt

$228 at Saks Fifth Avenue $228 at Nordstrom $228 at Neiman Marcus

Toteme The Slim 35 Croc-Effect Knee-High Boots

$1,130 at Matches Fashion

Insights, advice, suggestions, feedback and comments from experts

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Regarding the concepts used in this article, let's break them down:

Street style: Street style refers to fashion trends and outfits that are observed and photographed on the streets, often during fashion weeks or in urban areas. It is a source of inspiration for many people looking to spice up their wardrobe.
Winter outfit ideas: The article provides 25 winter outfit ideas to inspire readers to create stylish looks during the winter season. These ideas include different combinations of coats, knits, boots, and accessories.
Maxi skirt: A maxi skirt is a long skirt that typically reaches the ankles or floor. It can be made from various fabrics and is often worn for a more elegant or bohemian look.
Flat shoe: A flat shoe is a type of footwear that does not have a heel or has a very low heel. It provides comfort and is suitable for casual or everyday wear.
Cable knit sweater: A cable knit sweater is a type of sweater that features a textured pattern created by intertwining cables or ropes of yarn. It is known for its warmth and cozy appearance.
Wrap jacket: A wrap jacket is a type of jacket that wraps around the body and is secured with a belt or tie closure. It is a versatile outerwear option that can be dressed up or down.
Utilitarian trousers: Utilitarian trousers are pants that are designed with functionality in mind. They often have multiple pockets, durable fabrics, and a relaxed fit. They are inspired by military or workwear styles.
Midi skirt: A midi skirt is a skirt that falls below the knee and above the ankle. It is a versatile length that can be dressed up or down depending on the occasion.
Chunky knitted turtleneck: A chunky knitted turtleneck is a sweater with a high, close-fitting collar that covers the neck. It is made from thick yarn or knit, providing warmth and a cozy look.
Knee-high boots: Knee-high boots are boots that reach up to or just below the knee. They come in various styles and materials and are a popular choice for winter footwear.
Leather jacket: A leather jacket is a jacket made from leather, typically cowhide. It is a timeless and versatile piece of outerwear that can add a cool and edgy touch to any outfit.
Knit sets: Knit sets refer to coordinated outfits consisting of a matching top and bottom, both made from knit fabric. They are convenient and stylish options for those looking for a put-together look with minimal effort.

These are the main concepts used in the article. If you have any specific questions or need more information about any of these concepts, feel free to ask!