You should also have a way to cool off quickly, either by removing a layer or unzipping. If you get sweaty, the moisture will chill you layer, so don't let yourself get TOO warm. (Antiperspirant doesn’t hurt, either. Some folks put it on their feet to keep their feet warmer.)
Ok, what about shoes? Shoes are tricky, because they’re in contact with the ground, and you lose heat much more quickly through contact with solids/liquids than through contact with air. (See also: contact frostbite. See also: why 50 degree water feels colder than 50 degree air).
Your shoes have two goals: adding bulk around your feet, and insulating them from the cold ground. If you’re buying new winter boots, size up so they fit with extra insoles (without pinching your feet, which makes them--you guessed it—colder). I like to add a 13mm wool insole.
Then—and this is key—take out the insoles after every time you wear the boots so they can dry fully. (Or buy a boot dryer!) If your boots are damp, even a tiny bit, even if you can’t even feel the dampness, they’re gonna suck the warmth right out of your toes.
That’s also true with base layers, which are your innermost layers of clothing, the ones that touch your skin. Your skin is moist, and cotton can chill you when it’s damp. If you wear a base layer made of polyester, merino, or silk, you’ll feel warmer throughout the day.
HATS. It’s a myth that you lose 40% of your heat through your head. You just lose heat from anywhere that isn’t covered, which may or may not be your head. Neck gaiters and wrist warmers can help with this, too.
You can also get some disposable hand/toe warmers. Even if you don’t use them much, keep a pack in your pocket just in case. I sew a little pocket in my hats so I can tuck a hand warmer against the back of my neck, which feels super cozy.
If you’re very cold, hear me out: put a hand-warmer in your crotch (but not against your skin, which can burn you and cause a whole other problem). It’ll warm your femoral artery, which, in turn, helps to warm your whole body.
I think that covers it for clothing. But here are some non-clothing tips for when you’re outside and you’re already cold.
Movement will warm you up, but not all movement is equal. I’ve found that the sweet spot for me is anything that raises my heart rate but doesn’t make me out of breath. Try walking, jogging, or doing knee bends.
Go to the bathroom frequently. A full bladder will make you a lot colder. But don’t avoid drinking so you don’t have to pee—ya gotta stay hydrated, too.
Meals make you colder, because blood goes from your extremities to your digestive system. But snacks make you warmer! I like to keep chocolates in my pocket.
When you get back inside, you may be tempted to keep your layers on as you warm up again. After all, they make you warmer, right? Nope!

Your coat and your boots hold cold, just like they hold warmth. Strip down to your base layer and bare feet and you’ll warm up more quickly.
Fat holds temperatures, so you have more body fat, it may take you longer to get cold—but it can also take you longer to get warm again. A hot shower or bath will usually cut straight through any chill.
And in general, when you're inside, embrace coziness! Hot drinks, a fire in the fireplace (or candles), blankets, knitting--it's all part of winter, and there's something really special about coming in from the cold and drinking hot chocolate by the fire as your ears warm up.
Finally: Everyone's different. There's no right or wrong way to enjoy winter. It's all about finding what's right for you. ✨
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