How Women Can Dress Stylish in the Winter

Watch the video above from my YouTube channel to discover my tips for how to look put together when the weather turns colder

If winter makes you think of frumpy, oversized sweaters and sloppy style, think again. Here are my three tips for how to dress stylish in the winter.

Stock up on the basics

woman dressed in three basic outfits black tops and jeans


Having the right pieces in your closet ahead of time eliminates frustration with creating stylish outfits in the winter, and also throughout the year.

This means it’s time to stock up on the basics. You need to have core colors in high quality sweaters and layering pieces. Color and fit matter for stylish winter wardrobes.

These basics are unifying items that allow you to create outfits easily and to have fun playing with bolder colors and prints.

To determine exactly which items you need to make it through the winter looking stylish, check out my three step system to a capsule wardrobe.

Lighten up your layers

Cassandra Sethi wearing layers


Consider creating three layers to your winter wardrobe to transition quickly from a freezing walk outdoor to an overly heated indoor environment.

A t-shirt, light sweater or jacket, and a coat typically allow for a variety of temperatures, indoors and out.

Here I’m wearing a lightweight cashmere turtleneck, with a very lightweight cashmere cardigan then layered under my overcoat.

It’s three layers, but doesn’t look like too much because of the lightweight choices I’ve made. Check out this closer analysis of the fabrics and weights I’m choosing this winter.

Protect your ankles

look stylish in the winter by wearing ankle length pants


Ankle length pants are trendy, but not really the best option for the colder winter months.

There’s no reason to have freezing ankles for the sake of dressing stylish in the winter, so invest in some full length socks. Coordinate the sock color with your pants. With these dark blue pants I use black or navy socks.

The tan trousers in the middle are paired with tan socks.

This prevents your socks from being a distracting part of your outfit by choosing the wrong color. Since they are similar colors, they blend into the outfit and you will have warm feet all winter.

My personal favorites in socks that I always recommend to my women’s personal styling clients are from Tabio. I discovered them in Japan and wear them each winter to keep my feet toasty.

Picture of Cassandra Sethi

Cassandra Sethi is a NYC Personal Stylist and Image Consultant. After working over 15 years in the Fashion Industry, most recently as a Senior Buyer for Equinox, she created her business, Next Level Wardrobe – a luxury personal shopping service for successful professionals.

Next Level Wardrobe has been featured in Wall Street Journal, Today and CNN. See here.


For immediate help to upgrade your work style (virtually or in person), use this link to apply for a style consultation.

To receive my complimentary guide, 3 Items You Need In Your Closet Today, click here to put in your name and email.

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Cassandra Sethi sitting on s stool, black and white photo