5 Boots You'll Love All Winter Season
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Today I’m sharing my top favorite winter boots, as we transition from fall into the winter season. I compiled a list of my current 5 favorite boots/styles, and how I styled them myself. You can read through, or scroll until you find your personal favorite!
TIMBERLAND BOOTS (exact, but different color) | BLACK JEANS (similar) | WHITE SWEATER (similar) | SOCKS | BEANIE
1) TIMBERLAND SHEARLING BOOTS
COLOR: “Medium brown/dark sand” | SIZE: True to size. Wearing 7.5.
So many positive things to say about these waterproof shearling boots! I first posted about these after I wore them on my Toronto, Canada trip in 2019, and I had so many questions about them! These boots are super high quality and comfy, and withstood the rainy weekend we had, puddles and all. I wore them for 12+ hours, being at a conference one day, and exploring Toronto on foot the next day. They still look almost brand new 5+ years later. I have them in the “medium brown/dark sand” color. They come in several other colors, which you can find all of them in this post on LTK.
UGG MINI PLATFORM BOOTS | SHOE REPEL SPRAY | SLOUCHY SOCKS
2) UGG CLASSIC ULTRA MINI PLATFORM BOOTS
COLOR: “Sand” | *SIZE: Runs true to size, BUT size UP if you’re in between sizes. I have a size 7 (usually 7.5) and it’s too small with thick socks.
(Updated April 8, 2025) My new favorite pair of boots, the classic platform womens’ UGG’s! I have them in the color “sand” as shown, but I was also eyeing the color: “Driftwood / White Pepper”. They have a somewhat similar pair on Amazon, shop it here. I also LOVE and have been eyeing the women’s UGG Tazz II Slipper in color “chestnut”. I use the Jason Markk Repel Spray from Amazon and it’s helped my UGG’s repel liquids and dirt over time!
CHELSEA BOOTS | SKINNY JEANS (similar) | BEANIE | SHERPA JACKET (similar)
3) CHELSEA BOOTS
COLOR: “Taupe/Stone” | SIZE: True to size. If in between, size up half a size. Wearing 8.
After spending all weekend on my feet in Gatlinburg, TN, I’m here to report back that these Howler Chelsea Boots are the bomb. They’re both cute and comfortable! The ones I’m wearing are the “taupe/stone” color, but they also come in black! They’re just short of $100, but there are many similar ones out there, including this boot from Amazon.
SIMILAR POST YOU MAY LIKE: “Travel Guide: Vacation in Gatlinburg, TN”
BOOTS | JACKET (similar) | JEANS | FEDORA HAT | TOP (Amazon) | NECKLACE | BAG
4) “LIGHT NUDE” MID-CALF BOOTIES
These faux leather mid-calf booties are so pretty and chic! I love that they have a pointed-toe, and the contrasting vegan suede heel makes it so unique. They’re fitted around ankles, which is a huge plus, because it’s hard to find boots that aren’t so wide around my tiny ankles…so they’re definitely flattering! These are also under $50 and fit true to size! They have quite a few colors + patterns, including: snakeskin, black, olive green, and an off-white color, aka “bone.” My current color featured here is “light nude.”
SQUARE-TOE BOOTS // STRAIGHT JEANS // LOW BACK TOP (similar)
5) SQUARE-TOE MID-CALF BOOTS
COLOR: Both in “Black” and “Bone” (off-white) | SIZE: True to size. Wearing 7.5.
These square-toe mid-calf boots are GORGEOUS. The off-white color is my favorite, but is unfortunately sold out at the moment. You can also try getting on their waitlist, and Lulu’s will notify you once they’re back in stock! They also have these boots in black… you bet I have both colors! The fit is amazing, and they are under $50 + true to size (TTS). Wearing a 7.5 here. I will update you guys on my Instagram once there has been a restock… so keep a look-out!
QUICK TIP: pair them with thick socks. The soles are a little uncomfortable, but once you have a thick sock, you can wear them all day. (I’ve personally tested this a few times.)
If I find any more boots that I think you guys may love, I’'ll be sure to update this post. Hope y’all have the best week!
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