What to wear with Over the Knee Boots

Whatever you do, don’t wear your over the knee boots with a spandex cut-out dress. Unless it’s Halloween of course. As I’ll talk about more in depth below, over the knee boots tend to cut your silhouette in half. So, it’s best to keep your whole look slim and lengthening. Skinny jeans, tailored skirts and even shorts for the daring are all great options. Full skirts have also been touted as an over the boot outfit option. But, unless you’re super tall and super thin like a runway model, I think full skirts will definitely shorten your look. And the look is very dated (and not in a vintage chic way–more of a farm girl’s loose in the city in 1982 kind of way), in my opinion.

Wear Over the Knee Boots with Skinny Jeans

If you want to wear over the knee boots with any type of jean, you pretty much have to go with skinnies since they’re the only jean that will fit inside your boot! Skinny jeans are also a great way to dress down your boots and prevent your look from becoming more scandalous than you’d like. To dress down even more, wear a plaid flannel or a stylish t-shirt.

Wear Over the Knee Boots with Tailored Skirts or Dresses

Tailored skirts help maintain a long and lean look that will keep you from looking like you’ve shrunk a couple inches or are standing in a hole. Go with a pencil skirt or a well-fitting tulip skirt if you’d like a little more volume. Mind your length to prevent trampiness (unless that’s what you’re going for, of course!). No shorter than a couple inches above your boot is a good rule of thumb. It’s true you can go bare-legged with this look, but if you’re trying over the knee boots for the first time or are wanting to lengthen your look, try wearing tights or leggings that are the same color as your boots.

Wear Over the Knee Boots with Shorts

If you’re a super daring fashionista, try over the knee boots with shorts and leggings. If you go with this look, I suggest matching your leggings to either your shorts or your boots–or both! The shades can be slightly off, but this monochromatic look will lengthen your look and ensure a sophisticated vibe rather than an I-belong-on-the-street-corner vibe.

Getting the right look with Over the Knee Boots

Just because we think of Julia Roberts when we think of over the knee boots, that doesn’t mean that is the look that is trendy this season. We’re not talking about how to take a hooker boot and make it safe to wear everyday. Over the knee boots for Fall 2009 are subtle in everything other than their height.

Choose the right heel

Avoid stiletto heels when shopping for over the knee boots. Instead, find a more modest heel like a wedge or a tapered chunky heel. And, keep your height moderate–I suggest no more than a 3 inch heel. Flat over the knee boots are also an option, but can be challenging if you feel that the extra height of the boot makes you look shorter.

Color and material

Avoid patent leather at all costs! Instead, find a boot in suede or natural leather. If black feels a little too close to Julia’s boots, go with a tan or brown boot instead.

How to Wear Over the Knee Boots

Over the knee boots can be challenging for certain body types. That doesn’t mean over the knee boots aren’t right for you. Of course, if you still don’t feel comfortable even after trying these suggestions, go with a different type of boot–feeling comfortable and confident in what you wear is of utmost importance!

If you’re short

Over the knee boots have a tendency to cut you in half. If you’re short, this can make you look even shorter. You don’t have to wear 4 inch heels to lengthen your look. Instead, make sure you minimize the number of visual breaks by wearing tights or Skinny Jeans in the same color as your boots. For a super lengthened look, wear a pencil skirt, tights and over the knee boots all in the same color.

If you’re tall

If you’re tall, over the knee boots can make you look even taller. And, they have a tendency to make you look like a hooker no matter what the rest of your outfit is. To avoid this, wear a pair of flat suede over the knee boots with skinnies and a long cardigan. The jeans and long cardigan will tie the boots into the rest of your outfit, making them less of the primary focus.

If you have healthy thighs

Of course, gossip magazines are making an issue of thigh spillage over the tops of over the knee boots. It’s nice to see celebrities are human, too. First of all, make sure your boots fit. If they’re too tight at your thighs, forget thigh spillage–the bottom line is you’ll be uncomfortable! Once you find the perfect pair, wear a pair of tight leggings to prevent any thigh spillage you might be worried about.

Over the Knee Boots Under $100

Your thoughts?

I’m a fan of over the knee boots, but will probably buy an affordable pair since I think it may be a fleeting trend.
What’s your take?