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How to Wear Thigh High Boots

I’ve been dying to get a pair of thigh high boots for years. For awhile, I was obsessed with the Stuart Weitzman boots that every blogger and their mom had. But I’m glad I never pulled the trigger because, sadly, the Stuart Weitzman boots have gone out of style. Luckily, there are a lot of other thigh high boots to choose from that I think are a more classic option than the Lowland Boots.

Sézane Thigh High Boots with skirt outfit

Outfit Details: Sézane Sweater c/o || Sézane Shirt c/o || Sézane Skirt c/o || Sézane Boots c/o || Sézane Bag c/o

How to Wear Thigh High Boots

It’s no surprise that Sézane has an amazing selection of thigh high boots and over the knee boots. I was torn between the Colette Boots and the Anaelle Boots. I think the Colette boots were sold out in my size at the time so I opted for the Anaelle boots. Spoiler alert – they are amazing and couldn’t be happier with my choice!

Sézane Anaelle Boot Review

The Anaelle boots are a suede, wader style boot with a 3.1in heel. A side zipper allows you to get in and out of them a little easier. The shaft measurement (from middle of arch to top of the boot) is about 25″ – plus and minus one inch between the back and front. I’m wearing the Anaelle boots in Taupe but they are available in other neutral and colorful shades!

Neutral fall outfit from Sézane

I’m either an 8 or 9 in Sézane shoes but I took my larger size (size 9) and I think they fit perfectly. Since Sézane doesn’t have half sizes I definitely think you can take your larger size. As you can see from the photos, they do come up over my knees a good bit. I’m 5’8″ and have long legs and they still provide a lot of coverage. I was worried that my legs might be too skinny for these boots but I think they have the perfectly slouchy fit. And I don’t feel like they will fall down my legs – the leather is pretty substantial and holds it shape.

Neutral fall outfit with over the knee boots

Thigh High Boots with a Wool Mini Skirt

This is probably my favorite way to style my thigh high boots! For a while, I was kind of uncomfortable wearing mini skirts because I felt like A LOT of skin was showing. And in the fall/winter I would end up getting to cold – even with wearing tights. Thigh high boots are the solution to these problems since provide more coverage AND warmth!

This is actually a head-to-toe Sézane look. Sézane really kills it every year with their fall/winter releases. The Malia skirt is a favorite of mine and you can see it styled here as well. The Samuel Jumper is so soft and cozy but it unfortunately sold out soon after it was released. I’m wearing it over the Max shirt which is a great oversized button down shirt. I finished off the look by adding the Romie bag in black to break up all the tan/brown shades in this outfit.

Thigh High Boots with a Plaid Slip Dress

The second way to style thigh high boots might be a little unexpected. I know that thigh high boots look great when you show them off. But sometimes it’s nice to have them be a little less noticeable. I decided to pair my new Freda Salvador MOLLY boots with a fall slip dress.

How to style thigh high boots with a slip dress

Outfit Details: Jenni Kayne Dress || Freda Salvador Boots c/o || Everlane Blazer

The Jenni Kayne Winona Slip Dress is a new addition to my closet and I’m OBSESSED. I think it’s the perfect fall transition dress. The material is a cotton blend that feels pretty light and delicate. It is light enough to be worn in warm weather and easily layered up for fall/winter. I plan on wearing this dress with sweaters, layered over light turtlenecks, and a variety of jackets and blazers. I’m wearing it with my Everlane blazer but I also think some print mixing would look good – like a plaid or houndstooth wool blazer.

Freda Salvador Molly Boots Review

I recently add the MOLLY Boots to my Freda Salvador collection. And honestly, I can’t believe that after my years long search for OTK boots that I was able to get 2 pairs in one season! These differ from the Sézane boots in that they are a western-inspired design and lower heel height. They also have an elongated and rounded shaft. Overall, I think this gives the MOLLY boots a more casual vibe.

I’m pretty much an 8.5 in all of my Freda shoes with the exception of one pair. I took the 8.5 in the MOLLY and I would say it’s a good size for me. They fit a little more snug in the toes than my other Freda shoes, since they have a pointed toe. I do have thin and narrow feet which is why I think the MOLLY in my true size still works. But if you have a normal to wide foot I would suggest possibly sizing up – especially if you want to wear thick socks with these boots.

I think the MOLLY boots are slightly more comfortable to stand and sit in because of the low heel and the elongated shaft. It allows your knee more freedom to bend and sit. The shaft height is about 25″ as well so it’s similar to the Anaelle boots.

Jenni Kayne Plaid Slip Dress with blazer.

I hope you enjoyed these thigh high boot outfits! I will be adding more outfit options to this post when I’m able to style them in different ways throughout fall and winter. So be sure to check back for updates or follow @jeansandateacup to see more of these boots IRL.

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