How To Style Over-the-Knee Boots

I live for boot season. I’m obsessed with booties worn with dresses and skinny jeans with riding boots, but my biggest obsession has to be my over-the-knee boots. In fact, the second the temperature drops below 65, I pull them out. These flat OTK boots have gotten so much use that, despite the fact that it costs more to resole them than what they actually cost, they will be worn again this year — and just as much as the last year and the one before. The look doesn’t tire, as it is easy to make them look so different every time. Here are a few ways to style over-the-knee boots.

  • How To Style OTK Boots 1 of 7

    Check out the many ways I have worn my OTK boots.

  • Not So Ladylike 2 of 7

    I wore my OTK boots during New York Fashion Week in February, simply because my hotel was far and I planned on using the transit system. These are my most comfortable walking boots. The pairing of this ladylike dress and boots even got me street styled in Essence magazine as soon as I got off the M train. 

  • The LBD 3 of 7

    When I get to work makeup events as part of Chicago's freelance artistry team, I am required to wear almost all black at times for most beauty brands. A simple little black dress, a sweater, and my OTK boots work perfectly.

  • Bold Colors 4 of 7

    The weather can be a bit crazy in Chicago — warm one day and freezing the next during the fall season. Last year, I kept half of my summer pieces (like these floral crop pants) and my winter pieces (like my boots) to mix, like I did here on a day when it was super sunny with a super cold breeze. 

  • Date Night 5 of 7

    Date night sometimes calls for a little more fun. I love wearing my OTK boots with an animal print dress or an oversized semi-sheer top, such as this one. I ended up at a blues bar that night to catch a live band. This was the perfect look for that moody place.

  • Brown & Black 6 of 7
    otk 4

    I really had nothing to wear on this day two years ago. I pulled together this all brown toned look at the last minute, and then realized that it was too slippery outside (and, not to mention, too matchy-matchy) to wear my heeled brown boots. I threw on my OTK boots at the last minute, and they did not let me down, like always.

  • Modern Vintage 7 of 7

    Heading out for another long day, I wanted to wear my $3 vintage dress and my boots, but it was a bit cold. So I layered on a simple sweater and a vintage velvet blazer for a modern vintage look. 

Article Posted 3 years Ago

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