Winter Boots: Round Up & Care Tips

Winter Boots Round up on Millay Blog

Alright, fall is basically over in New England and we have been dumped into winter territory rather abruptly, if you ask me. And since I’ve been on the hunt to replace a couple beaten up pairs of boots from my own wardrobe for the upcoming season, I thought it would be the perfect time to share some of my favorite finds plus simple tips I keep in mind when deciding what to invest in!

Criteria I look for in the perfect winter boots:

For me, the perfect winter boots have to be both stylish and practical. They need to keep my outfits looking polished and pulled together without making me wince in pain after a day at work, while ALSO keeping my toes cozy on cold winter days and safe when trekking across snow or ice. So let’s look at my checklist!

Block Heels

I am a big advocate of flat boots, which I have a couple pairs of, but I also know that I prefer to wear heels and add a little height to my disposition. That being said, for both comfort and safety, I go ahead and eliminate any stiletto-type heel (even kitten heels!)—they just don’t provide enough support throughout the day, and certainly not when traversing across icy, wet, or snowy city terrain. Style simply isn’t worth a twisted ankle to me.

Heel Height

The sweet spot I look for is between 2.5″ to 3″. After years of trying out different heights, I know this is my comfort and tolerance level, anything higher puts me in pain. I also really love the height this amount adds to my frame and to my outfit profiles. I’bve found them to be the most versatile in pairing with elevated going-out ensembles, work outfits, and even super casual outfits!

Timeless silhouettes and colors

This one can be tough for me as a lover of fashion because I LOVE the idea of experimenting and trying newer, more avant-garde styles. But I also know I have champagne taste (guilty!) and prefer to invest in nicer pieces, and that means focusing on shoes that can carry over year to year without going out of style.

My workaround? If there is a new style that I can’t shake out of my head (like a square toe, pilgrim-style adornment, or glitter covered calf boots), I simply add it to a wishlist and revisit it over several months and try to wait a year and see if I STILL love it. Longevity is important to me and this keeps me from spending a lot on things that will be more of an impulse buy than a worthy wardrobe investment.

A good example is over the knee boots, which I waited two years before buying, then felt confident spending $$$ on the right pair, which are now staples in my fall and winter wardrobe. Almond and softly pointed toes have felt enduring to me, and a good brown, black, and lighter neutral color are all a great foundation. I’m also not against a good print if it passes the longevity test!


This one is super important and an easy fix if you buy a pair that are lacking good tracking. If you get a pair of boots you love that have slick bottoms, TAKE THEM TO YOUR LOCAL COBBLER and have them add a traction sole to the bottom of your shoes. It will cost $20 or less and make the shoes not only more comfortable, but safer.


I’ve rounded up all my favorites on the market right now! I’ve linked to them all below, which include everything from my mood board above and more! Shop my boot picks:


Proper boot care

Another important thing to remember is that winter boots in particular are an investment, and need proper care to stay up to snuff — they really go through the elements of Mother Nature and need a little extra love to stay tip-top!

Regular Maintenance

Regular maintenance includes scuffing and brushing off chunks of debris on a regular basis and using quick leather wipes to make sure soot isn’t settling into cracks and the leather is staying conditioned and protected.

Suede should get a good spray of protective rain coating from time to time to keep moisture from ruining the finish. Brushing the nap occasionally also keeps the finish looking good.

Seasonal Maintenance

Buffing boots with a brush and conditioning leather finishes with a microfiber cloth at the end of each wearing season is super important. And if block heels are losing their luster or my heel caps are looking worn down, I take them to a cobbler to get resoled and touched up.

When putting boots in storage, try filling the interiors either with shoe shapers or crumpled craft paper so they keep their shape.

That way, when you pull them out next season, they look pristine, you’re excited to wear them again, and they are ready to go!


Shop my boot care tool kit below:


Hope you got a useful tip or two from this post! I just ordered the Emerson Fry ankle boots (after wanting them for two years) last night, so I’ll let you know how I like them. 🙂


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