How To Dress Stylish For Cold Weather

personal stylist

top: C by Bloomingdale’s, coat: Ted Baker, scarf: Nordstrom Collection (similar), leggings: Hue, boots: Ecco, gloves & hat: San Diego Hat Company, earrings: Alexis Bittar, bag: Liebeskind

I am aware I have no business saying I am freezing in London while a polar bear sits on the face of New York, but I’m shivering in my boots. It’s what I get for living in a city that hit 84° the day I left.

Usually I encourage packing minimalist for trips, but that doesn’t quite work for me in London, especially when my trip involves Fashion Week. Dressing delightfully stylish in cold weather is a challenge all its own for a San Diegan, but packing it all up for a three week trip included extensive planning. But that is beside the point. Let’s just say my suitcase was over the weight limit and move on.

Avoid Black

Doesn’t matter how fabulous your black attire is, everyone is wearing it. That alone is depressing. Basically anything besides black is a great idea, but color is really how to dress stylish for cold weather. My red Ted Baker coat always cheers me up and styles me out on my travels to the east coast and London.

Head And/Or Feet (“And” for me)

I know you have seen those fabulous street style images of women in cold cities sporting fabulous coats and then no socks with their sweet sneakers. I’m sure you have also seen women in heels. Man alive that is just not possible for me. But if you do want to try some dare devil looks that don’t involve socks, cover your head. I find if the top of your body is snug as a bug in a rug, the exposed bottom, like your feet, can survive lower temperatures. This works the other way as well. If I cover up my legs and feet appropriately, I don’t need as warm a top. The key elements though is your head and feet. If they are perfectly warm, you can wear less in the middle.


Leggings are essential to a stylish and flattering look in cold weather. My go-to leggings are from my pals, Vince and Vince. Vince and Two by Vince Camuto provide us with thick, soft leggings that flatter our torso with its wide waist band. I also like Hue’s Ultra wide waistband Leggings.

Note: Vince runs small, and Two by Vince Camuto runs very big. Hue runs true to size or maybe a bit small. As a size 4/6 woman, I wear a medium in Vince, an extra small in Two by Vince Camuto and I wear a small, sometimes medium, in Hue.

Double Up

In order to wear those fabulous tights, chic leggings, or kicky boots, you are going to need to double up in really cold weather, or as I like call it 45°. When wearing tights, I wear two pairs. I wear two pairs of leggings, and I most certainly wear two pairs of socks when I am not wearing proper thick socks. This tip will save your life and your style. Simply put your intended, more stylish layer on top. Underneath the suede leggings pictured on me, is a pair of Two by Vince Camuto leggings.


When you are covered in layers, sometimes the most stylish thing you can do is your make-up. I especially love to have elaborate eyes as I never wear sunglasses in cold weather. A red lip is also lovely.


Cashmere is amazing. Cashmere socks, turtlenecks, sweaters, dresses, and scarves are luxurious options for chic heat. Cashmere is available in most fashionable stores during winter (and on sale now – so stock up), but my go-to’s for cashmere are J.Crew, C by Bloomingdale’s, and Nordstrom always offers yummy cashmere options from Lafayette and Vince to their new line Nordstrom Collection. I put myself and many of my clients in their cashmere this season. My favorite find were these cashmere scarves by Nordstrom Collection.

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Photos by David McClory

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