Our Favorite Over-The-Knee Boots

October 7, 2015

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If you haven’t yet seen Shana’s New Style Rules for Fall, be sure to check it out. She has some awesome advice on how to update your closet for fall . . . with tips and ideas that are clear-cut and easy to follow. One of her rules is to “Wear Over-the-Knee Boots Like It’s No Big Thing.”

Over-the-knee boots are no longer the shocking, Pretty Woman inspired footwear they once were. The flat ones are downright practical – warm, comfortable to walk in, and so insanely chic. Throw them on over your workout leggings on your way to Barre class, slip them on with leggings and mini dresses all winter. Most will work with skinny jeans, too – even those pairs you’ve cropped, and are a much fresher option than tall boots.

I literally couldn’t volunteer fast enough to take on this post. I love boots! I’ll try them all! But doing this post actually changed my perspective quite a bit on how I shop. . . it’ll be interesting to see what you guys think.

Over-The-Knee Boots – Our Top Picks

Each boot below has been well tested, either by us at The Mom Edit, by our readers, or, in a few cases, 90+ glowing 5 star reviews on Zappos. Here’s our very favs:

TOP ROW

Stuart Weitzman 50/50, $655

Expensive, but these are THE over-the-knee boots. End of story. They’re truly, honestly comfortable, and the stretchy back panel fits many different leg sizes. Readers swear by this boot. (The black suede has been on Shana’s shopping list for a couple of years now. She’s just waiting for her existing Nine West OTK boots to wear out. Which brings me to my next point…..)

Nine West Tiberia, $189

Shana has an older version of these boots. She wears them all winter – so comfy, so warm, and despite alllll her best efforts, they haven’t worn out yet. There’s a bunch of pics on TME of Shana in these boots here, here or here (very last pic).

Blondo Eden Waterproof Boots, $285

This was one of our top selling boots on TME last year. Shana received email after email from readers raving about these boots. They’re comfortable, flattering, and insanely practical. (You can see these boots on one of Shana’s friends, Teri, in this article. Scroll to the bottom.)

BOTTOM ROW

Frye Shirley Over-The-Knee Boots, $498

None of the TME staff have tried these boots on, but we have a long collective history with Frye in general. (Hint: We heart Frye, big time.) And when the 97 glowing, 5-start reviews use words like “gorgeous, buttery leather” and “super comfy”….we’re not surprised. (Also available at Nordstrom.)

Dolce Vita Ohanna Over-The-Knee Boot, $280

The wood heel of these boots hit that perfect point of high, but not too high, and adds a cool vintage vibe. These boots come in gray (as shown) or tan. Both are stunning, and, according to reviewers, very comfortable as well.

Charles by Charles David Edie Boots, $199

The color is beyond gorgeous, the quality is so good, and the modest wedge heel makes them seriously comfortable. I adore these boots. I’d wear this oxblood color like it’s a neutral: WITH EVERYTHING. Instant outfit upgrade.

Blanket Coat by Steve Madden | Charles by Charles David Edie Boots

Over-The-Knee Boots – A Comparison

A pair of OTK boots were high on my fall shopping list. So, after a ton of research, I ordered a bunch to try on. I’m always one who gravitates towards the less expensive version of things. Shana would buy a sweater for $300 if she knew she’d get lots of wear out of it. I’d rather buy 6 sweaters for $50 each and have a variety to choose from. Generally speaking, neither of us is right or wrong, per se . . . but her clothes are ~~probably~~ much better quality. But here’s the thing . . . with shoes, boots, footwear of any kind . . . quality really, truly matters. Spending a little more means more comfort, durability and use in the long run. That couldn’t have been clearer with the boots I chose to try. In the future I’m going to focus on quality over quantity. (At least with footwear!) Here’s what I tried:

1. Steve Madden Rannsome Riding Boot

I love a good heel, but they need to be comfortable. The hidden platform makes these more comfortable and the stretchy material on the back of them keeps them from falling down. The only downside is that they’re difficult to take off . . . as in I need Zack to physically pull them off me. I wish there was a zipper. For some I’m sure this is a major deal-breaker.

2. N.Y.L.A. “Ashira” Boot

Hmm. These were just . . . cheap? Yes, they were definitely chosen (by me) because they were less than $90. See how it looks like I’m holding my ankle funny? I’m not . . . those are just the boots. Not to mention the fact that I’m normally a 7.5-8 and the 8’s were too small. I thought these were too good to be true when I saw them on Nordstrom’s website, and they turned out to be just that.

3. Charles by Charles David “Edie”

So Shana taught me a shopping lesson YEARS ago . . . she said if you ABSOLUTELY LOVE something, buy it, take it home and see if it works in your closet. Sometimes you’ll find that something you’ve been drooling over just doesn’t work with what you have . . . other times, it’ll be perfect and totally worth the money. In this case, one look at these boots and I was in LOVE. I ordered them ONLY to try them on and to include them in this article . . . I didn’t want to spend over $150 for a pair of over the knee boots. Once I compared them to all of the other (~~cheap~~ less expensive) pairs, however, I realized these were far and away worth the extra money. The quality is sooo much better than any of the other boots I tried.

4. Calvin Klein Jeans “Bisma”

If you can never find over-the-knee boots that will stay up, this is the pair for you. They’re tighter towards the top so they won’t slouch or fall but they’re made of stretchy material so they’re still comfy. (They come in suede or leather so you can choose the finish you’d like.) I couldn’t handle the tightness at the top . . . it’s not that they were uncomfortable, but I felt like my legs had a mini “muffin top” above the boots. They’d probably look better with tights but then I don’t need a specific pair of over-the-knee boots I can only wear with tights . . .

5. Steve Madden Suede Over-the-Knee Boots

I featured these with my favorite tunic top a few weeks back. Since I already had a pair of flat over-the-knee boots that I liked (and were comfy!) my choices above were all heeled. However. You know when something gets put into your head and then you just can’t get it out? And it ruins something you thought you liked? (Red Converse, Shana?) Yeah, so two words: Argh, matey . . . Now every time I put those suckers on I feel like I’m dressing up as a pirate. Dammit. Do I return them?? My sister, husband and mother all believe I should . . . (Does anyone know how to prevent these from falling down??)