What To Wear & Not Wear With Over The Knee Boots For Fall/Winter 2022/23! Dos & Don'ts Outfit Ideas

What To Wear and Not Wear With OVER THE KNEE BOOTS! These can be a challenge to style, so I wanted to give you some style dos & don'ts and outfit ideas so you can create outfits from your own closet. I have taken all the clothing from my own closet to create these outfits for you but if you like anything in the video there will be links below. If something is not available (NA) I will try to link something similar. As always, feel free to leave me any questions or comments in the comments section below!

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Knee High Boots

What I am wearing:

00:00 - Start
01:02 - Two Dresses - Longer & Mini
01:11 - Right Above The Knee Dress

01:49 - Mini Dress

02:38 - Sheer VS Opaque Tights

03:11 - OTK Boots With Sweater Dress

04:01 - Crop Cardigan & Mini Skirt

04:30 - OTK Comparison With A Knee High Boot & Mini Skirt
04:53 - Casual Sweater With Mini Skirt & OTK

05:25 - Faux Leather Shorts

06:14 - Blazer With Shorts & OTK Boots
Blazer Loft, NA Older Style

06:45 - Don't With Faux Leather Shorts
07:07 - Skinny Jeans & OTK Boots
07:15 - Buying Tip!

08:01 - Moto Jacket, Sweater, Jeans & OTK Boots

08:33 - Don't Loose Blouse, Jeans & OTK Boots

08:48 - Added Blazer To Top & Jeans Outfit

09:11 - Black Slim Blazer With Outfit

09:22 - Leggings Outfits

09:39 - Leggings & Oversized Sweater

10:11 - Don't White Lace Blouse With Leggings

10:21 - Don't With Blazer

10:38 - Yes - Shacket With Leggings

[wendychen]

This is great!! I love you including the "failed" outfits and talking through why it doesn't work and if you found a fix talking through the fix too!! Time to dust off my Stuart weitzman otk boots!! Woot woot!!

[joerubi]

I totally love this video. I also love that you included the "failed" outfits. I for one, have two pairs of Stuart Weitzman Fashion Boots: A pair of block heeled Tieland thigh high boots and the platform "Gotham" boot and I am looking to get at least two more pairs of SW boots to wear with my outfits. You are very stylish and fashionable. The black slim blazer with outfit, particularly skinny jeans, is my best outfit. 🖤❤

[annieirish]

I just want to say thank you for your very helpful videos and Merry Christmas!

[deborahgraham]

I have a pair of over the knee 'non-fitted' boots. They have more bulk than one your are styling here. What I have found is that the added bulk on the bottom balances out the looser tops that didn't work for you here (white blouse w/legging; loose black sweater w/leggings; and anything with a blazer). I have also found that non-fitted boots fit over leggings and skinny jeans really easily. The non-fitted boot works for me as I'm an apple shape with very narrow hips and thin legs but a tummy and wide shoulders. These boots help balance my naturally larger top with my naturally smaller bottom. I'm not sure how it would work for those ladies who have more of a pear shape or who are a bit hippy'er. Though it might balance the hip as well.

[lindacaffalette]

💟 Yes, totally agree with your choice of all black longer oversized sweater with the leggings & tall boots! Also the brown shacket outfit also looked great! Thanks...Merry Christmas & A Great New Year!
💟💜💟

[kimberlyperrotis]

I’m petite, so shorter skirts often end at weird lengths on me, like cutting straight across the kneecap. They can’t all be shortened, like the knit ones I love, but slim OTK boots look so much better with them than knee-highs, which leave a weird gap. Also, it’s annoying how the skirt sometimes sticks in the top of knee-highs, which are always too high and loose on my calves. I do love and wear knee-high boots a lot, too, with either longer or shorter skirts, just not those weird knee-length ones. The best thing about winter is wearing boots and layers.

[wendychen]

Fun fact they have fleece line tights with a fake skin look that give you extra warmth for winter!! Amazon carries them now!

[paddywarner]

Just found you
Love your videos
I really like that you show pictures of what doesn't work and then you explain why. I also love the comparisons.
So very helpful. Thanks again

[casebycase_]

Could you do one with colored over the knee boots pls?

[marshamarsha]

This was so helpful. You gave me lots of ideas for clothing combinations I already have. Thanks

[tracygray]

This was great! You provided some great examples and advice on what not to do. Have a wonderful holiday!

[kimberlyperrotis]

I love my Stuart Weitzman OTK suede boots. I’ve had a black, mid-heel pair for two years and just added a taupe pair, with a slightly lower heel. I want to wear them all the time, being a dress/skirt wearer. I try to limit myself to once a week for each pair, I want to make sure the feet sections dry out completely inside before wearing them again. (I once got athlete’s foot from wearing the same pair of boots daily, they were breathable natural suede, but once infected, they had to be discarded because they reinfected my feet every time I wore them). Over-the-knee boots are difficult to air out because of their length, so I started putting a desiccant packet into each toe, I hope that helps (I always save these from package shipping, so they’re free). Stuart Weitzman ones are expensive, but I wait for sales and really couldn’t recommend any other brand, and this is the kind of boot one only has to buy once a lifetime. For my color palette, the taupe ones are much better and the slightly lower heel is more comfortable. I love that they not too tight in the toes, as other boot brands always are (I’m a C, or Medium, width).

[EmilyWilliams]

Hi Jamie! Thank you so much for these ideas!!!

[margaretsabato]

I love your quilted bag. Where is it from? Happy Holidays! 🎅🎄

[molliemccollough]

Where can we get that wonderful black plaid blazer?

[soniapb]

I have been scared to try over the knee boots because of having large thighs. Great video.

[teresaquenneville]

Hi Jamie
Have you done a video that styles off white ankle boots. I purchased a pair and I love them, but I am struggling to find outfits that work with them. I feel like they cut me off and make me look short, so I end up switching them up for my black ankle boots. Help please!

[melissagriffin]

Too straight up and down for me but thank you