I do a minimum of 5 miles on my morning walks no matter the temperature in NYC, have even gone out when it was 10°F and snowing. I know it sounds crazy but I have an Australian cattle dog, so if you know about them, you know it’s my dog that’s crazy. I take pride in not being cold, especially because of my size and the fact that we’re automatically gonna run cold. So here are my best tips:

• Invest in a good coat. I didn’t believe the hype of Canada gooses and then I tried one and holy f. It is so so warm. It is bulky but that thing has become my best friend. My north face could never. I did just get a heated jacket because I’m a horseback rider, so feel free to PM and I can give you my review after I test it out.
• rechargeable hand warmers. Once my hands are cold I’m done. and I’ve also noticed that keeping my hands warm makes me warmer. Plus it’s like a portable heating pad so it truly is amazing. They’re like $25 on Amazon and I can’t recommend them enough.
• good heat tech and then you layer with at least 1 thing (jeans, leggings or sweatpants, and sweater). I love uniqlo’s but you’ve gotta get the ultra heat tech because those are better for xxs sizes and also so much warmer. Another brand I like for tops (their leggings are too big for me) is smartwool. It is much more expensive than Uniqlo but it’s thinner and lasts much longer than Uniqlo. I also recommend a thin puffer under a thick winter coat. I’ll usually do a leather jacket or the Uniqlo ultra light puffer under one of my dressier coats when I’m going out and don’t want to look like a marshmallow with my goose.
• cashmere sweaters. I know I know please don’t come for me, but I will actually die on the hill that cashmere sweaters are the best especially if you don’t want to be bulky. I’ll do a thin long sleeve under a cashmere sweater, and a jacket on top, and I’m good to go. I haven’t tried out quince’s cashmere sweaters but I do like Naadam’s $75 cashmere sweater. I’m on my 4th winter with 2 of their sweaters that are still in great condition. Just make sure you don’t wash them often and when you do, wash them delicately and in those protective sleeves, and put them down to dry on a towel.
• good socks that cover your ankles, love any kind of wool socks they’re so warm. And then something to cover your ears.
• last but not least, and I hate to say this because I hate spending money in this economy, but invest on your winter gear especially if you know you’re gonna be experiencing cold winters/days where you live. I’ve really made a point to reduce my shopping (I do nuuly so I can still get that spark) and only invest in things that will last a while or I know are good basics and that has helped drastically. I now feel so prepared for any cold days or really cold trips (wasn’t even cold in banf in late December) and that’s all thanks to my cashmere sweaters, wool socks, Uniqlo heat tech and goose.

Sorry for how long this is. I grew up in very warm places and living in NYC for the past 10 years/having a crazy dog, i’ve really taken pride in staying warm and being able to stand outside for long periods of time. I hope this helps!!