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Fªte the 5050: Our Favorite Over the Knee Boots for Under $200

Kate Moss for Stuart Weitzman

This season marks the 20th anniversary of Stuart Weitzman’s 5050 boot, a leather and stretch-fabric boot that’s a perennial classic. To celebrate, Weitzman has released the boot, which is beloved by celebrities and real-life women alike, in an array of new materials like luxe suede (in tan, ocelot, emerald and navy) and shiny patent leather. Another reason to celebrate? The designer opened his 100th store this year, in Milan, with a huge celebration attended by Kate Moss and fashion’s biggest names during Milan Fashion Week. The flagship boutique, designed by famed architect Zaha Hadid, marks a new turn for the brand, which is injecting itself with a more youthful energy.

The over-the-knee boot silhouette isn’t exclusive to Weitzman’s 5050, but celebrities love his version thanks to it’s easy pull-on, pull-off functionality. Cool uptown girls such as Olivia Palermo pair the boot with the layered outerwear, while L.A.’s celeb set, including Angelina Jolie, wear them with skinny jeans and cozy knits. Want the look without paying the $600 price tag? We’ve got our favorite over-the-knee boots, which will give an instant update your wardrobe whether you’re dealing with autumn chill or a seemingly never-ending Indian summer, all under $200.

Olivia Palermo

Angelina Jolie

Franco Sarto Motor

Classic Cool

The Franco Sarto Motor ($179) is the closest we’ve found to the classic Weitzman 5050. It boasts the same leather and fabric combination that’s made the 5050 so popular, but adds an extra panel of leather at the heel, which allows the boot to retain its shape (and hides any bumps and rolls that your jeans might leave behind).

Fans of the preppy look or equestrian style will want to jump on this boot before the real chill starts to roll in.

Available at Piperlime.

Calvin Klein Averie

High Style

For those of us that need a boost in the hight department, the Calvin Klein Avery ($199) offers the over-the-knee shape in sumptuous suede and gives a boost with a four inch heel. It’s got a slightly pointier shape, which means this boot is a little dressier and gives the illusion of a longer leg. As a bonus, it’s the only boot that we found where you can fold down the shaft and wear it as an under-the-knee boot if you need to dial down the sex appeal.

Available at Bloomingdale’s.

Steve Madden Creation

Western Addition

If all-black is just too dark for everyday, or you just need to add a little more color to your shoe rotation, opt for the Steve Madden Creation ($100). It’s got the slimmest fabric panel, which gives the boot a more luxe all-(faux)leather look. But it’s also the most rugged of our choices, not only because it’s brown, but because it’s got a looser and more distressed look than the black over-the-knees we’ve gathered. If you’re into flannels, distressed denim and Southwest style, these are the boots for you.

Available at Piperlime.

Report Gwyn

Golden Girl

We love a simple black boot, but sometimes you need a little something to amp up your style. The Report Gwyn ($130) adds an asymmetrical gold zipper to give just a taste of embellishment without going over-the-top with your over-the-knee. It’s the highest boot we’ve chosen, so it’s definitely going to fit a little bit higher on your leg. Combined with the peek of gold, this boot oozes sex — so be ready for some major attention.

Available at Piperlime.