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Since the season of over the knee boots has arrived I thought it may be helpful to break down what you should be looking for when shopping and some options at different price points. I kid you not, I had probably ordered 20-30 pairs before I finally splurged on my Stuart Weitzman Lowland boots so I have a bit of experience when it comes to boot shopping. Although mine aren’t the most budget friendly, they were the answer for me. I’ll explain a little bit more below when I break down the do’s and don’t and share some more affordable options that live up to the hype!

When first approaching any item of clothing or accessory you want to be clear on whether this is a trend or investment buy. Although I originally though a pair of over the knee boots would be a trend I would wear one season and get rid of, that has proven to be very wrong. I’m glad I ended up treating it as an investment item in the long run because I can’t tell you how often I wear mine! 

Once you have figured that out and have a price point in mind let’s talk specifics:

Heel:

Flats versus Heels. This was a tough decision for me because the heeled versions are so pretty and make your legs look amazing! Although I desperately wanted the heeled version I knew that a wardrobe staple like this would get far more use from me if it was a flat. Looking back, I’m so glad I went that route because since having Zain I am allergic to high heels. 

Leg Fit:

This was the real kicker for me! 90% of the boots I sent back didn’t fit my legs. With an over the knee boot you want the shaft to be somewhat fitted so you get that nice lean elongated appearance. The boots I ordered were always baggy and ill fitting especially at the top. Even with a tie, I couldn’t get them to stay up and I certainly didn’t want to be pulling them up all the time. This fit was what really sold me on the Lowlands! Although I hated the price tag once I tried them on there was no turning back. If you have slimmer calves and are having a hard time finding something that fits I totally reccomend them!

Material:

The luxe leather used in the Stuart Weitzman boots are not comparable to anything I’ve owned before. These boots were my first pair from the brand but the material is exquisite and doesn’t lose it’s shape over time. With more affordable options know that they are most likely made from synthetic materials and will not keep shape as well or last as long. Again, if these aren’t an investment piece you want around for seasons to come this shouldn’t be a huge factor. 

Round vs Pointed Toe:

This was another internal struggle for me. The edgier side of me prefers a pointed toe boot but since these were such an investment for me I decided to go with a classic round toe. My hope is that I can get more use out of them and that they don’t go out of style in the near future!

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Once you’ve narrowed these decisions down it’s time to get shopping. I’ve broken down boots into 2 categories: Under $200 and over $200. These price ranges are normally high for me but I think with boots and over the knee boots especially anything that is quality will cost you a little bit more. If you happen to find any other pairs or already own a pair that you love that I didn’t included please send me a note, I am happy to update with reader favorites! 

 Over The Knee Boots Under $200

Over The Knee Boots Over $200

Hope this helps you on your search and happy boot season!