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 a never-ending befuddlement regarding temperature, or maybe I'm just plain bad at guestimating 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 11 degrees outside, and I finally realized what it meant to be prepared (or should I say the need to be prepared) for the seasons. Below, I've highlighted six of my errors made that fateful winter and how you—and let's be real, myself included—cannot endure the same mistakes again. See my tips, shop the picks, you know the drill.

Up next: the 20 best winter boots you won't even have to break in.