What to Wear When It’s Freezing in Winter

December 20, 2021

Everlane Puffer - What to Wear When Its Freezing in WinterThe recent temperatures and wind chills in New York have made a simple errand down the block seem like an Olympic sport. These have been some of the coldest days I’ve experienced since moving to New York a decade ago and man, has dressing these days become tough. 

Dressing for when it is really cold is an art – and can feel like rather a lot of work if you don’t know where to begin.

If you, too are experiencing freezing temperatures, today’s post is for you.  I’m sharing all my favorite pieces for dressing when you’re experiencing a big chill, blizzard or polar vortex. 

What To Wear When It’s Freezing In Winter

Meghan Donovan styles Everlane puffer jacket - What to Wear When Its Freezing in Winter

Base Layers

For staying warm in really cold weather, base layers are of the utmost importance. Uniqlo’s HeatTech makes up my base layers for most of my cold weather outfits when needed. It adds necessary extra warmth and I don’t find it as bulky as a lot of other brands of long underwear. It helps regulate your body heat for extra warmth and will keep you both warm and dry. I think it is essential cold weather clothing.

HearTech is also really affordable which I appreciate. The line has expanded so in addition to having tops and bottoms, they also offer HearTech socks, accessories and even Extra Warm versions of some of their most popular styles. I own the crewneck style, the turtleneck and the tights. I always pack them for my Vail Ski Trips because they are essential base layers when skiing.

The line is available for Men, Women, Kids & Babies. If you decide to buy some HeatTech I’d recommend sizing up. I was far more comfortable in the Large tops than the Mediums. 

I also love my Athleta leggings for cold days. They are thick and sturdy and keep me warmer than other brands.

Looking for tights that’ll keep you warm as a base layer? I find Spanx to be the best, thick + warm tights for cold weather outfits.

LL.Bean Boots I wit & whimsy


For when it is really cold, you’ll want to prioritize fabric like alpaca, wool and cashmere. Sweaters are the perfect middle layer this time of year but not all are created equal when it comes to being dressed warm.

I tend to wear cashmere all winter long. I invest in Jenni Kayne cashmere (find my favorite Jenni Kayne styles) & NAADAM cashmere and for more affordable options, I also look to Bloomingdale’s Aqua cashmere and Everlane cashmere.

Best Coats for Women


Living in the Northeast, I have a whole coat closet that allows for nearly every style and every weight needed during Winter. When it comes to dressing for cold weather, I think coats are most important.

For really cold weather, it’s a puffer jacket for me. I live in my Everlane one which has long cuffs to keep your hands more warm and a hood for wind protection. It’s the best for extremely cold days.

LL. Bean Boots I @meghandono


I like a boot that is functional but still stylish.

L.L. Bean boots are a classic option for Winter. While they don’t keep your feet very warm they are great for trekking in the snow and I also wear them in Fall, too. If you wear them in snow, I recommend pairing them with wool socks.

For a more stylish winter snow boot, I rely on my two colors of my Marc Fisher Izzie Boots.

For socks to keep your feet warm when it is freezing, stock up on merino wool socks. I like Bombas Merino Wool Socks.

A Guide to the best of the Vail Valley I wit & whimsy - What to Wear When Its Freezing in Winter

Marc Fisher Izzie Snow Boots

I’ve also lived in my UGG boots the past few years – especially when going to/from workouts when I don’t want to lace anything up and want to seamlessly slip in / out of them. 

And if I’m dressing up, I reach for ankle boots and jeans that will cover taller, warmer socks.

Meghan Donovan styles Everlane puffer jacket - What to Wear When Its Freezing in Winter


There’s nothing worse than cold hands and feet so no winter outfit is complete without the right winter accessories. We’re talking hats, gloves and scarves. Uniqlo has a good variety of Winter Accessories to complete your look and I also really like Everlane’s selection.

I keep a selection of beanies and scarves on hand and rotate them in based on what outfit I am wearing.

. . .

H&M Sweater // Everlane Puffer (c/o – available in 3 colors + a long version) // Jeans // LL. Bean Boots // Scarf

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[Bekka Palmer Photography]

comments +

  1. caitie says:

    the 30-40 degree weather has felt like a heat wave compared to the past few weeks! this is the first time i’m hearing of the uniqlo heattech line. i’ll totally have to check it out! warm base layers are a must.

    • Meghan says:

      SO crazy that 30s to 40s feels like a heat wave but truly couldn’t agree more! DEFINITELY try out heattech as a boston girl! It’s been saving me these past few weeks and I’m only regretful I waited so many years to buy it!

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