How-To Dress When You Hate Cold Weather

(The picture above was taken in Bellingham, WA in February 2017.)

I never learned to dress for the cold and maybe that’s why I despised it. But after living in Bellingham, WA through the winter on a sailboat, you bet your ass I figured it out.

Well, thanks to my fiancé Chris. Chris helped me it out.

My #1 first-world problem is always fashion vs. function and how to combine the two. Through many trials and errors, I’ve figured out a few tips that I hope will help you, too!

For example, I’m now a wool/cashmere believer. They are the best natural fibers (and don’t retain odor!) that will keep you warm when it’s anything but.

Cashmere tip: Buy second hand! You’ll find pretty nice cashmere at thrift stores, especially in the summertime when people are cleaning out their closets. I haven’t paid retail for cashmere ever and I don’t intend to. (I was a fashion designer for 10 years and I know how companies jack up the price.) If you think a piece may be pure wool or cashmere, double check the care tags to make sure it’s not a blend. Also, flip through racks all around the store. You can even score sweet pieces in the men’s and boys section!

Ok, without further ado, here are a few tips that have inadvertently turned into a Smartwool and REI ad. Just click on each image below to go to the product to hook yourself up. These make sure great presents for your loved ones, too.

(*No, I’m not being paid by Smartwool or REI, but I should be. Hello, Smartwool? REI? Anyone there?)

How-To Dress for the Cold When You Hate Cold Weather:


Merino Wool Tank: If you buy anything for the winter, let this be it. The soft wool tank hugs you close and keeps your core warm, which I’ve finally realized is the most important part of not freezing your nuts off! I layer this under t-shirts too when I want to rock my bellbottoms and Allman Brothers shirt when it’s 50 degrees outside. (I realize some of you reading this may think 50 degrees is actually warm, but I’m a wuss! What can I say! 🙂 )


Merino Wool Pullover: On top of that bad boy, slip into the “zip top!” It’s black and looks chic (or, at least you can fake it because it’s black). The best part, it goes perfectly under a fur vest – just because it’s cold as fuck it that doesn’t mean you can’t still look cool!


Neck Gaiter: You can totally make one from an old sweater if you’re up for it. I suggest making or buying one that fits closer to the neck instead of a more boho-looking cowlneck. The point is to keep the wind from slipping down your neck and giving you the chills.


Merino Wool Base Layer Bottom: Another go-to that is thin enough to pair under leggings or jeans. Remember those bellbottoms I mentioned earlier? These make them totally functional in wintertime. A fashion/function win!

womens pendleton sock with classic yellow, red, and green stripe with snowflake ankle detail

Wool socks: Basically the best present ever, because who thinks to buy socks anyway? Plus, these are super cute and will look good poking out of your ankle/shin boots with leggings, if you know what I mean. I think they sell packs of Pendleton socks at Costco, too.


Bama Sokkets: These save my freakin’ life. Wear these in rain or snow boots to wick sweat from your feet and keep your toes warm! I swear! You have to try it to believe it. These babies are perfect for rain boots, too. (You know how rain boots can be a little big and clunky on the foot? Not with these babies. Your boots will stay comfy to your feet and you won’t feel like you’re on the verge of frostbite.


Wool hats: Hats are so personal and really the only way to showcase your unique style when you’re all bundled up. I usually wear a brimmed hat or a beanie. The brimmed hat is perfect to keep rain and snow out of your eyes. The beanie is classic and, when positioned correctly, can make your hair look super fly. I recommend putting a chin strap on a brimmed hat (you can buy them separately), to prevent strong gusts of wind from blowing it off your pretty head!

*Another tip? While you’re at the thrift store scoring cashmere, check out belts for kids – they make the best accessory to wrap around a brimmed at.

Do you have any favorite pieces to keep warm and look fashionable? We’d love to hear them in the comments below!

I learned how to dress when I was going through an existential crisis. Catch up on the series!

Existential Crisis (Part 3)



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