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How to Wear High Top Sneakers

How to Wear High Top Sneakers

There are shoes you can wear with almost anything, high top sneakers are NOT one of them. Just because they are cool and casual doesn’t mean you can throw them on with just any outfit. 

One reason for this is that high tops demand attention. They dominate almost any outfit you pair them with. But, this is what makes them great for styling and experimenting in various ways. No matter how you choose to wear them, high top sneakers have a few rules to them. But first …

Types of High Top Sneakers

The type and design of the sneakers you choose to wear will influence how you pull off the look. Thin sneakers such as Converse and Chuck Taylors are those made of thin fabric and typically extend to just below the ankle. 

If you wear them wrong, thin high tops can make your ankles and legs look thin and disproportionate, especially when worn with something baggy. You should also not tie them all the way up to the ankle, but leave some cuff room for comfort and a contemporary edge.

Mid high tops are a bit bulkier due to the material used on them–think of Air Jordans or Vans Sk8-His. These are the classic high tops that can be pulled off in almost any look and with any ensemble due to their forgiving “average” look.

High neck top sneakers look like boots because they have a higher heel collar extending slightly past the ankles. Their unique look makes them slightly harder to pull off, but are great for a dark-colored outfit to help tone down their dominance.

Tips for Styling High-Top Sneakers for the Guys

Those who have been sneaking around the block longer know that there is not a look you can’t pull off with a good pair of high top sneakers. That includes activewear, casual, smart casual, and even dress-up looks. 

With Jeans

Thin sneakers and skinny jeans make up the look of the decade. Even the ladies got in on this long ago. If you decide to wear mid high tops, go for a slightly bulkier look with straight legs or bunch up your skinnies at the ankle to leave some skin showing.

For high neck sneakers, you will want to go with a solid color sneaker and dark jeans to tone everything down. You can choose to tuck in your jeans at this point, but well-fitted straight legs can also flare nicely at the ankle to correspond with the sneakers.

With Other Types of Pants

For a more upscale but still casual look, a pair of fitted chinos or cargo pants will make a killing. However, stick to the classic colors such as olive, khaki, black, navy blue, or grey and throw a tee and jacket on top to touch it up.

A nice Oxford shirt also works great with chinos and bold high-tops, but make sure the shoe is of the high-end kind. Or how about a pair of tapered sweats, perhaps with cuffs, for the ultimate athleisure look? It is easy to pull off, incredibly casual, and great for a weekend stroll.  All you need is a designer pair of high top sneakers to accentuate the look.

With Shorts

Shorts and high-tops? Shocking!

Well, perhaps not so much considering that with a baggy short, a pair of high neck sneakers, a casual Oxford shirt, and legs that definitely don’t skimp on leg day – this is a look that can work. Anything else and you might just end up looking like a punk.

With a Jacket

One way to bulk up the top and compensate for the bulk of mid high tops or high neck sneakers is by using a good jacket. A leather or denim jacket works wonders, and all you need to do is cool it with some accessories. If you’re feeling even bolder, a designer blazer, trench coat, or even a camo jacket all work great depending on what you wear underneath.

How to Wear High Top Sneakers for Ladies

Classic Chic: Skinny Jeans and Sneakers

This is a cut-and-dry look. Almost every pair of jeans you have will work with high top sneakers. Tubes, “mom” jeans, and skinnies all work great, just make sure to follow the rules regarding thin sneakers.

Dress Them Up

Little dress, maxi dress, midi dress, skirt – there is nothing you can’t pair with high top sneakers. Going to a party? A maxi dress with sneakers is a look every woman has tried, but they probably were not high tops. Well, now try again with some thin or mid high top sneakers and see your dress transformed. Color it up with glasses and a statement bag and you’re good to go.

You know that little dress you have been itching to try out? A pair of thin sneakers or white mid-highs work great to help bring out your legs. A midi dress does even better when matched with statement high tops. The options are literally endless.

Wear Them With Leggings

You may have done slip-ons with sneakers, definitely with tennis shoes, and maybe even with boots. Now try an even sportier look with thin sneakers with an oversize top, crop top, or turtleneck for date night. 

With a Jacket/Blazer

One of the top trends with high top sneakers this year involves layering up with a jacket or blazer. This is especially true if you have mid high tops or high neck top sneakers. The effect of a somewhat baggy and casual jacket offsets the size of the shoes and creates an incredibly chic look.

If you don’t happen to have denim jackets or leathers lying around somewhere, a boyfriend blazer is a great way to pull off this look. Make sure to have an equally bulky pair of pants, preferably jeans in a block color such as black.


High top sneakers have been around for quite a while, and only the bold can continue to pull off a fresh look. Both dudes and gals have to work a bit harder to get the look right, but it is always absolutely worth it.

Thin sneakers are relatively easy to pair with skinny jeans and pants, but mid high top and high neck top sneakers might be sneakier to pull off. The goal is to balance the look, and these tips here will get you pulling off a killer look right up there with the best of the fashionistas.