How Women Can Dress Stylish in the Winter

October 21, 2020

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.

About the Author - Cassandra Sethi
About the Author - Cassandra Sethi

Personal Stylist & Image Consultant

Cassandra Sethi is a Personal Stylist and Founder of Next Level Wardrobe, a luxury Personal Styling and Shopping Service that helps successful professionals of all ages and sizes. After working in the fashion industry for over 25 years, she used her expert knowledge to create a proprietary styling system called ‘The Next Level Wardrobe Style System' which guarantees clients more outfits with less items in their closet. NLW has been featured in The Wall Street Journal, The Tamron Hall Show, NY Mag, Huffington Post and more.

*Disclosure: Next Level Wardrobe only recommends products that we’d suggest to our clients or personally wear ourselves. All opinions expressed here are our own. This post may contain affiliate links that at no additional cost to you, Next Level Wardrobe may earn a small commission. Read the full privacy policy here.

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Cassandra Next Level Wardrobe Bio Picture

Cassandra Sethi

is a NYC Personal Stylist and Image Consultant. She is the Founder of Next Level Wardrobe and 'The NLW Style System' that guarantees clients more outfits with less items.

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