Here I listed them from the least to MOST warm for a helpful resource. (all just in my own opinion with my experience wearing them)
Light warmth (40 degrees and above)
Hunter Boots - perfect for slush and snow but they MUST be worn with very thick socks in the winter. I would not recommend for temps below freezing or for extended time outdoors. They are waterproof and almost indestructible - so they can be helpful in bad weather. If you have the gloss version I highly recommend this product to keep them glossy.
Sperry Saltwater - this pair is waterproof but not super warm under freezing temps. This is the perfect boot for if you live in a warmer climate than Michigan. I pair mine with thick socks but wouldn't recommend them for extended wear outdoors under freezing. They work great for early winter, late winter or quick in and out of the car errands all winter.
Medium Warmth (30 - 40 degrees, colder if with super warm socks)
SOREL Joan of Arctic II wedge - this pair is great for everyday wear in the winter like errands, carpool or looking dressier even when it's cold and slushy. These boots are waterproof but have little insulation. I like to wear ankle socks with mine. The deep treads make it easy for maneuvering safely in snow and slush. These are not for extended outdoor wear in temps at freezing or below. In and out of the car is perfect, really cold football games or sledding wouldn't work.
UGG Wedge (similar or similar) - like the Joan of Arctic II wedge this pair is waterproof, has a great tread but little insulation. Wear with socks for errands. I wouldn't recommend for long periods outdoors. This exact pair is sadly no longer available, but I linked to similar options.
SOREL Lexie Wedge (similar) - this pair also great for everyday wear and is a little warmer than the Joan of Arctic II wedge because they go up higher on the ankle and I would say they have a touch more insulation. They are waterproof and the deep treads make maneuvering in snow and slush safe. I pair mine with thick warm socks which make them warmer than the lace-less wedges too.
SOREL Harlow Bootie - this pair has more insulation than the wedges and is also waterproof. You can pair with thick socks or regular socks depending on the weather. The only concern is you will want to keep this pair away from salty snow to avoid stains. They also have a great tread for safety.
Very Warm (30 degrees and below)
UGG Bailey Boot - this is by far my favorite of the bunch. I am an UGG lover - tried and true. I know some people hate them, but those people must not live in a state where it snows for 6 months. Haha! These are SO warm and feel like a hug on your foot. I like this button version because sometimes I fold them down for an ankle boot look with the fur showing. They work for long periods outside, but since they are suede I don't recommend them for snow play (sledding, etc). I wear these with NO SOCKS as they are designed that way. They naturally insulate your feet. I have two pairs I love them so much. Try to avoid salty snow and slush with these because of staining. And use the boot spray to protect them. You can also replace the insoles on these!
SOREL Tofino II with faux fur - this is by far the warmest pair I own. They are also waterproof and perfect for super snowy and cold days and extended time outdoors for activities like sledding, hiking or just playing in the snow with kids. I prefer this pair to the very bulky classic Joan of Arctic boot. I bought that boot and had to return them because they were just so heavy and big feeling on my feet.
Now on to your questions!
Q: Winter boots and work clothes, how do you make it work? My SORELS don't look right?
A: When I worked outside the home I wore winter boots to work and then brought my "real shoes" separately and changed when I got to work. It depends on your office environment and comfort desired. But you are right! Winter boots don't look great with slacks.
Q: Boots that are not too heavy! I'd like to find a cute pair that I can wear all day.
A: The UGGS and SOREL Tofino aren't too heavy at all and very very warm. Depending on what your day brings you may not want to wear them all day though. For all day wear I like the wedge boots.
Q: Do you use any waterproofing treatments on your boots?
A: I recommend this product (or something similar) for suede (UGG & Harlow) otherwise all the rest of the boots listed are waterproof on their own! But to be honest I am TERRIBLE about spraying my boots. I haven't in like 5 years. So, I mean do as I say and not as I do!?!? Haha.
Q: Waterproof, warm, for dog walking. Recommendations?
A: It depends on where you live. In the Northern states or the northern East Coast I recommend the SOREL Tofino II. If you live south of Tennessee or the southern east coast I would recommend the Sperry Saltwater - simply because they are cheaper and you don't need the intensity of insulation of the Tofino.
Q: Dying to find a pair that are warm and good for serious winters but also lightweight.
A: The SOREL Tofino are the warmest boots I own and are much lighter than the Joan of Arctic boot (which felt like wearing weights on my feet).
Q: Boots that I can wear to work so I don't have to bring to pairs of shoes. (I got a lot of this question)
A: I am TEAM BRING AN EXTRA PAIR. But that's just me. I recommend the SOREL Joan of Arctic II wedge if you really aren't into bringing two pairs. Those are the most dressy.
Q: Any cute boots that cover your ankle? Hat the pant/shoe gap.
A: With this in mind I would go for the SOREL Tofino or this style. Both will get your ankles covered!
Q: Looking for stylish but actually warm! I live in Chicago.
A: All of the pairs are cute in my opinion and work for Chicago weather! Pick your warmth level above and you are set to go!
Q: Good boots for teens/tweens?
A: My daughter and I are now the same size and we share a lot of these. Her favorite are Sperry Saltwater (and you know, kids are never cold so they work for her even when it's too cold for me to wear them) and UGG Bailey Boot. She has a pair of SOREL Tofino for sledding, outdoor activities or really, really snowy days. That is her order of preference too!
