The Perfect Winter Boots

I’m on a hunt for the perfect pair of winter boots. I feel like I do this every year (I live in Chicago after all)… so far I haven’t found the pair. This year I am not just looking for warm, cute, and functional, I’m also looking for super easy to put on and take off since, these days, I am typically doing that with a baby in tow.

Do you have a great boot suggestion for me? I’m totally torn, but I’ve collected a few options and divided them into a save vs splurge list. The fact that I am torn probably means that I’ll just wear my old duck boots for another year. Help please.

Winter Boots | Splurge vs Save


What do you think of these? I wish I could pull off moon boots because they are comfortable and warm, but I can’t – at least not since I was 10. I think my favorites are 2, 6, and 10.

What are you wearing?

Have you joined the Baby Registry giveaway(s) yet? They end on January 27th!


7 thoughts on “The Perfect Winter Boots

  1. I’m a walker…and pregnantc so for me, comfort and slip-on ability would be key…but stores get so tetchy if you want to actually test drive boots (or anything really,) so in terms of look only, I love 4, 2, than 8.

    • I hear you! Last year I really wanted to wear moon boots because they are easy to take on and off… and allowed for my swollen feet to fit :). I never bought them but only because I didn’t want to add bulk to my already growing body.

  2. I can provide no assistance here and am actually looking for a pair myself! Would love to hear any updates you have for this! Also willing to shop for them and report back or of course shop with you 🙂

  3. I have a pair of the Hunter Boots and love them! Super easy to slip on and off with baby!

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