I’ve been in deep denial. I’ve been lying to myself. Some days, Chicago plays along — giving me balmy afternoons in the 50’s. But on a day like this Monday, I can’t deny it any more. Winter is coming. It’s cold November raining sideways right now as I write this. Soon that rain will be snow. Soon the streets will be icy. It is my least favorite thing about living here, to be honest.

Moving to Chicago has taught me entirely new things about footcare and the shoes I need to wear. For years I read fashion magazines and gazed at gorgeous boots in fall fashion spreads. I thought cute, chic booties were in the cards for me. Unfortunately, I have flat feet, bouts of plantar fasciitis that require orthotics for long walks, and an extreme fear of falling on ice and breaking something — so during winter I’m not only all-flats-everything, but I’m conscientious about tread and arch support as well.


There are 7 kinds of winter boots on my list as Chicago necessities and go-tos — I’m still building my collection over here! Here are the 7 kinds of boots I need to make it through this and every winter. Tell me your favorites in the comments!



1 — Cute easy leather slip on sneaker boots. Half of the time that I’m running around the city, I’m in what my dad refers to as a “push toe shoe.” Meaning, a slip on. All summer I’ve been in Birkenstocks, Bucketfeet, Converse and my beloved Nike Airmaxes that are honestly on their last legs because I wear them almost daily. On chilly days like today, I’m most likely to wear my Ugg Australia Women’s Croft Sneakers. I never really thought I’d rock Uggs until these came into my life. I love a sheepskin lined shoe in weather like this. I’ve got my eye on the Keds Women’s Juliet Winter Boot next, it’s got great reviews and looks right up my alley.


2 — Real rain boots. For years I tried to fake the funk with leather (or pleather) boots for rainy weather. Inevitably, I ruined quite a few pairs of boots. I think it’s time that I invest in a real deal rain boot. Most ladies in Chicago rock Hunter boots, which can be stylish, but aren’t an option because I have bigger calves. I’ve got my eye on the Sperry Top-Sider Women’s Saltwater Quilted Nylon Rain Boot — for years Luvvie’s been telling me about Sperrys. This may be the year that I make the investment!



3 — Hardcore snow boots. I hate to acknowledge this fact, but it’s always best to be prepared. At any given weekend, Chicago weather can take a turn for the snowy. It’s best to invest in some real deal snow boots. I absolutely love my Sorel boots, they don’t PLAY. I have the Joan of Arctics, but I’d also rock the Sorel Women’s Glacy Explorer Snow Boot (and don’t overlook these).



4 — Timbs. I grew up in the 90’s as a hip hop fan, but didn’t live in a cold weather place back in those days. So confession time — I’ve never owned a pair of Timberlands. I know. Ridiculous! I think it’s FINALLY time. But I can’t decide — black or tan? Or maroon? Amazon Fashion has a great selection!



5 — The classic LL Bean Duck Boot. For the past two or three years they’ve been at the top of my list. What makes them a coveted classic? The LL Bean Duck Boot has been made in Maine since 1912 and is known for high quality, long lasting insulation against bitter cold. Sure, other brands make duck boots that look very similar, but I don’t care — I want the Bean Boots! Every year, I ask for these boots for Christmas and every year they’re backordered until the following year. But reportedly they’re expanding their production facility, so fingers crossed. Maybe I can get a pair by my birthday! I’m not asking for much, LL Bean — just a pair of raven blue duck boots, I’m a size 10 normally so I’d need to size down to a 9, right? Let a bella know. I’m ready to step into these vintage classics.



6 — Dr. Martens. My love for Docs is well known and well documented. Currently I have I think 5 pairs, ranging from red plaid to purple to leopard mary janes. Oddly enough, I don’t have a pair of regular wear-all-the-time black Docs, like these. I think it’s about time.



7 —  Hush Puppies Women’s Cyra Catelyn boots. If you’re a reader of this blog then you know I love vintage brands — they’ve been around forever for a reason, right? That’s part of my love for Hush Puppies, they’ve been making high quality footwear since 1958. Their Cyra Catelyn boots currently come in 21 different colors and styles. I’ve got a few and they’re perfect for early fall (before the snow and ice and slushy wetness). Click here to buy a pair!


Those are my favorites and must-haves for the season and in general. See any of your faves? What are your must-have winter boots?

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pets says:
November 30, 2016, 6:32 am
Get Timbs in maroon.
HotBeauty says:
December 1, 2016, 12:53 pm
All of these are nice but I really need to check out those Hush Puppies. It seems like Hush Puppies makes a comeback every 10 years. LOL!
Kiss & Make-up says:
December 2, 2016, 4:07 am
Would love a pair of Dr. Martens, for old times' sake ;-)
Alisa says:
December 3, 2016, 7:32 am
I love your collection and want to buy some?
Reena says:
December 5, 2016, 4:12 am
Thanks for the round up of cruelty-free bloggers – some blogs on there that I haven’t yet followed! Also, thank you so much for featuring mine on there too, was a lovely surprise!
alexie fashion says:
December 8, 2016, 6:30 am
There are the best place for those looking for suitable for any age and i love it. Are you provide delivery service?