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.

1

Simple & Chic

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (3)

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

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (4)

H&M Double-Breasted Wool-Blend Coat

Vince Brushed Flannel Maxi Skirt

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (5)

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Vince Venice Slingback Flat

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (6)

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

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (8)

Belle & Bloom Eternal Flame Tie-Waist Wool-Blend Coat

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The Frankie Shop Maesa Pleated Wide-Leg Cargo Pants

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (9)

The Frankie Shop Maesa Pleated Wide-Leg Cargo Pants

Frame + Ritz Paris Embroidered Suede Baseball Cap

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (10)

Frame + Ritz Paris Embroidered Suede Baseball Cap

3

Simplicity City

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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

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (12)

Iris & Ink Charlie Merino Turtleneck Sweater

Mango Ribbed Midi Skirt

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (13)

Mango Ribbed Midi Skirt

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Aeyde Teresa Leather Knee Boots

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (14)

Aeyde Teresa Leather Knee Boots

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4

Layered Leather

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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

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (16)

Generation Love Milan Vegan Leather Blazer

Vince Leather Buttoned Shirt

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (17)

Vince Leather Buttoned Shirt

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Miu Miu Quilted Leather Top-Handle Bag

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (18)

Miu Miu Quilted Leather Top-Handle Bag

Now 14% Off

5

The Knitty-Gritty

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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

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (20)

Misook Textural Stripe Mock-Neck Cable-Knit Tank Top

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Misook Textural Striped Knit Midi-Skirt

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (21)

Toteme The Slim 35 Croc-Effect Knee-High Boots

These 25 Winter Outfits Make Getting Dressed for the Cold Easy (22)

Toteme The Slim 35 Croc-Effect Knee-High Boots

Insights, advice, suggestions, feedback and comments from experts

As an expert and enthusiast, I have access to a wide range of information and can provide insights on various topics. While I have personal experiences or emotions like a human, I can provide factual information and answer questions based on available data.

Now, let's discuss the concepts mentioned in this article.

Winter Outfit Ideas:

The article provides 25 winter outfit ideas to inspire readers to spice up their winter wardrobe. It suggests various combinations of clothing items and accessories to create stylish and fashionable looks for the winter season.

Street Style:

Street style refers to fashion trends and styles that emerge from everyday people on the streets, rather than from high-end fashion designers or runways. It is often influenced by the personal style and creativity of individuals, showcasing unique and unconventional fashion choices.

Winter Wardrobe Slump:

The term "winter wardrobe slump" refers to the feeling of getting stuck in a rut and wearing the same uninspiring outfits during the winter season. It is a common phenomenon where individuals may feel bored or uninspired by their winter clothing options.

Style Inspiration:

Style inspiration refers to finding ideas and motivation to create fashionable and stylish outfits. It can come from various sources, such as fashion magazines, social media, fashion shows, or street style.

Midi Skirts:

Midi skirts are skirts that fall below the knee and above the ankle, typically ending at mid-calf length. They are a popular fashion choice and can be styled in various ways to create both casual and formal looks.

Leather and Textured Fabrics:

The article mentions the use of leather and other textured fabrics as a way to add interest and uniqueness to winter outfits. Leather is a versatile material that can be incorporated into jackets, skirts, or accessories, while textured fabrics like flannel or knits can add depth and visual appeal to an outfit.

Oversize Outerwear:

Oversize outerwear refers to coats or jackets that are intentionally designed to be larger and looser than the wearer's actual size. This style trend has gained popularity in recent years and can provide a fashionable and cozy look during the winter season.

Basics with a Twist:

The article suggests that incorporating basics with a twist can create easy and foolproof outfit formulas. This can include adding funky denim, colorful striped sweaters, or structured oversize outerwear to elevate a simple outfit.

Public Speaking:

While not directly related to the article, I noticed a mention of "public speaking" in one of the search results. Public speaking refers to the act of delivering a speech or presentation to an audience. It involves effectively conveying information, ideas, or opinions in a clear and engaging manner.

Please note that the information provided above is based on the snippets from the search results. If you need more specific information or have any other questions, feel free to ask!

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