6 Winter Dressing Mistakes I Can Personally Confirm Are Awful

I aim to live my life with no regrets. However, when it comes to the subject of my inability to dress for the weather, I'm afraid a few come to mind. Ask the majority of my friends, and they'll likely tell you they've spotted me in at least a handful of ill-suited ensembles for whatever the occasion happened to be at the time. Perhaps it's due to the fact that I come from California where the ambiguous weather has instilled in my mind never-ending befuddlement regarding temperature, or maybe I'm just plain bad at guessing what works for what temperature. (I pray for the former, but it's probably a mix of the two.) Whatever the case, I guess what I'm trying to say is I've made mistakes, and now I'd like for us all to learn from them.

I moved to the East Coast about three and a half years ago, and upon my arrival was greeted by a humid, muggy mid-June rainstorm. I was puzzled by the notion of precipitation while summer was around the corner, but I trudged onward. Fall arrived, and I was pleasantly delighted by the crisp air and changing leaves. Seasons aren't so hard to navigate! Then winter struck. I remember a day it was quite literally 11ºF outside, and I finally realized what it meant to be prepared (or, should I say, not be prepared) for the seasons. Below, I've highlighted six of my errors that fateful winter and how you—and, let's be real, I—can avoid the same mistakes in the future. See my tips, shop the picks, you know the drill.

Mistake: Forgoing Socks or Tights


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Give those gams the love they deserve and accessorize with a pair of stylish socks or tights stat.

Mistake: Not Investing in a Coat


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You're kidding yourself if you think you can get through winter sans coat. I should know—I tried for about a month my first winter in New York, and I suffered… greatly.

Mistake: Neglecting Your Phalanges


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There's perhaps no more alarming feeling than the tingling sensation of numb fingers. Protect thyself.

Mistake: Wearing Weather-Sensitive Shoes


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Skip the stilettos unless you plan on being transported by car the entire day (lucky you).

Mistake: Layering Improperly


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And by improperly, I mean not layering at all. Layering is key! The Vast Importance of Layers: my forthcoming book title.

Mistake: Skipping the Beanie and Scarf


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A warm neck and ears are the key to winter stamina.

This story was originally published at an earlier date and has been updated.

Next, These 9 Winter Boot Trends Are Starting to Feel Dated, so We're Replacing Them

Nicole Kliest
Freelance Contributor

Nicole Kliest is a freelance writer and editor based in New York City who focuses on fashion, travel, food, wine, and pretty much anything else that's amusing to write about. After graduating from Pepperdine University with a bachelor's in journalism and creative writing, she started her career back in 2010 as Who What Wear's photo editor and throughout the last decade has contributed to publications including Fashionista, Harper's Bazaar, Elle, The Zoe Report, PopSugar, Fodor's Travel, and several others. She also copywrites and has worked with clients such as Frame, Sea, 3x1, Intelligentsia, and others to develop brand voices through storytelling and creative marketing. She's very passionate about the ways we can improve our sustainability efforts in the fashion industry as well as cultivating content that's diverse and inclusive of all people. When she's not checking out the latest restaurant opening in her West Village neighborhood or riding her bicycle along the West Side Highway, she can be found scheming her next trip somewhere around the world. (Up next is Vienna.)