Trending: How To Wear Tall, Over-the-Knee Boots

Tall, over-the-knee boots are all the rage this season. They add an instant high-fashion look to any ensemble and can dress up even the most basic sweater and jeans.  Tall boots are one of our favorite trends this season, but we’ll be the first to admit that wearing over-the-knee boots can be intimidating. Finding the balance of high-fashion without going Pretty Woman can be a little tricky. All we can picture is poor Julia Roberts walking into that snotty Beverly Hills boutique in her patent leather thigh highs and being asked to leave. Yikes!

However, these days over-the-knee boots are actually totally wearable and chic. All it takes is knowing how to wear them. Stuart Weitzman’s 5050 boot (and its subsequent dupes) is by the far the most coveted, iconic over-the-knee boot that strikes a perfect balance between wearability and runway style. It comes in a short stacked heel and perfect length that hits just above the knee, so you can wear it anywhere with just about anything. Flatter, riding-style over-the-knee boots are always going to be more wearable than their high-heeled counterparts.

Flat Boots

Splurge! Left: Stuart Weitzman ‘5050’ Over the Knee Boot, $635
Steal! Right: ‘Eden’ Over the Knee Waterproof Boot, $199

High Heeled Boots

If you want to go more va-va-voom you can go for a high heeled over-the-knee boot like  Jimmy Choo’s ‘Gypsy’ boot. These are, of course, a bit more tricky to wear to places like the office or with skirts, but are doable with the right styling.

Splurge! Left: Jimmy Choo Toni Suede Over-The-Knee Boots, $1795
Steal! Right: Nine West ‘Chorus’ Over the Knee Boot, $80


It’s all about balance. The one key point to always remember when wearing over-the-knee boots is balance. For example, if you do opt to wear an over-the-knee boot with a shorter skirt, make sure you wear a looser fitting top. In other words, a short body-con dress alone will look a bit over-the-top with tall boots. If you want to go body-con, try long sleeves and layer with an oversized coat or a chunky knit sweater.

Miranda Kerr pulls off the body-con and over-the-knee boot combo with an oversized Alexander Wang coat.
Miranda Kerr pulls off the body-con and over-the-knee boot combo with an oversized Alexander Wang coat.


If you want a more everyday look, pair over-the-knee boots with longer hemlines. If you want to go shorter, pair with tights. This is a comfortable, wearable look for someone who wants to be more understated.

Easy-wearing knee-high-boot looks.
Easy-wearing knee-high-boot looks.

Leggings & Oversized Sweaters

Adding dense leggings with a long tunic or sweater is also a great way to wear tall boots and still stay modest and comfortable. Pair boots with a chunky, oversized sweater that falls below your backside. Style with a statement necklace and some stacked bracelets for an easy fashion-forward look.

Go comfortable and understated with leggings and an oversized sweater.

Skinny Jeans

Of course, the most turnkey pairing is denim and over-the-knee boots. There’s no basic top or pair of skinny jeans that won’t stand to gain serious style points by being paired with tall boots. It’s like an instant fashion-lift. Pair skinny jeans, tall boots, and a button-up top or layer a top and vest for an easy, ultra-chic look.

photo credit: Lucky Magazine
photo credit: Lucky Magazine
photo credit: Pinterest
photo credit: Pinterest




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