Simple. Save the Winter boots and really heavy warm stuff unless it's actually freaking cold outside! It's the fashion don't I continually attack while nobody says a damn thing about the look like I'm a bluffing idiot. I think back to the little girl I seen in Bermuda shorts and big Winter boots on a rather warm December day in nearby Pearland, TX. I can't truly comment on what works because I don't have too much cold weather fashion knowledge. The important thing to me is that you dress up according to the weather. You don't wear short-shorts and flip-flops on a snowy day in Helsinki. You don't wear furry Winter boots tucked into jeans on a Summer day in Phoenix or Honolulu.
I guess I'll go back to Christmas Eve 2004 here in Houston. My mother recommended I wear one of my sweat pants. I was wearing longjohns underneath and wearing some of my sneakers. I know somebody's going to disagree with me, but there is no style with trying to stay warm. You're mostly dressing to stay warm and not out to look cute. Like my mom said on a cold day once when I was at the mall, "it's too cold to try to look cute!" That's when I've mostly seen lots of flip-flops, cropped jackets, and that sort of thing on... either a 40s or 50s degree day (Farenheit, of course).
If you were to learn from me- a guy from a place where it doesn't get bitter cold too often for too long, just dress normally and only wear warmer garments on colder days. I have a few jackets. One is a windbreaker while some others are for cool days. I have two coats for very cold days. My mom is basically my stylist. She'll tell me right away to avoid wearing a certain garment or garments for specific days. I usually ask her what it's like outside. Invest in some cold weather clothes, understand what it's like outside, and for a better-safe-than-sorry, get some clothing for really cold weather and ONLY wear those if it's that cold. Best advice- dress accordingly.