5 Affordable Boots You'll Love All Season

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SQUARE-TOE BOOTS // STRAIGHT JEANS // LOW BACK TOP (similar)

Today I thought I’d share my top favorite winter boots, as we transition from fall into the winter season (finally)! I compiled a list of my current 5 favorite boot styles, and how I styled them myself! You can read through, or scroll until you find your personal favorite! Click any of the photos or links to shop the item directly.

1) 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.)

 
 
 
 

BOOTS // JACKET (similar) // JEANS // FEDORA HAT // TOP (Amazon) // NECKLACE // BAG

2) “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.”

 
 

TIMBERLAND BOOTS // BLACK JEANS // WHITE SWEATER (similar) // SOCKS // BEANIE

3) 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 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 2+ 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.

 
 

CHELSEA BOOTS // SKINNY JEANS (similar) // BEANIE // SHERPA JACKET (similar)

4) 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, sitting right at $52.

SIMILAR POST YOU MAY LIKE: “Travel Guide: Vacation in Gatlinburg, TN”

 
 

PLATFORM BOOTS // JEANS ($22)

5) WHITE LACE-UP PLATFORM BOOTS

COLOR: “White” | *SIZE: Runs big! Size down half a size. Wearing 7.

Last but not least, I’ll finish off this post with one of y’alls favorites from my IG Stories—these white platform boots! I posted about them thinking that not many would love how chunky and white these are, but apparently it was a hit! I absolutely love these, and to be honest, I’m not sure why, lol. I was afraid they’d be too much. But every time I put them on I feel so confident and edgy, I love it. These are just short of $60. Side note: SIZE DOWN HALF A SIZE. I am usually a size 7.5, but these fit perfectly as a size 7. They also come in black!

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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