How to Wear High Tops

Co-authored by Jordan Stolch

Last Updated: April 2, 2024

High tops have made a resurgence. Best known as a trend from the 1980s, the high top sneaker has made a comeback with a wide variety of colors, styles, and brands - the shoe has even become upscale with labels like Isabel Marant, Viktor & Rolf, and Michael Kors designing their own high tops. High tops can be difficult to pull off because the shoe is so dominant. However, paired with the right outfit, high tops can really put together a look and make you look unique, modern and fashion forward.

Part 1

Part 1 of 2:

Deciding on High Tops

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Think carefully about what style to get. Which type of sneaker do you want to wear: thin or thick? A thin high top is something like a pair of Converse sneakers, shoes made of a light fabric that, when tied to the top, rests snugly against the leg. An example of a thick version would be a Nike Air Force 1 or Reebok Freestyle that is wide at the ankle and has more bulk.^{[1]
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- The issue with thin high sneakers is that if tightly laced all the way up to the top, the shoes can make your ankles look awkward and small.
- With chunkier sneakers, be aware that they might make your feet appear larger than they are.
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Think about what brand you like. What have you purchased in the past? What brand not only looks great but fits your feet? Converse? Nike? Reebok? Or do you want to go upscale and wear Raf Simons, Michael Kors, or Isabel Marant sneakers?
- The most important thing to remember when buying high tops is to ensure that they're a good fit. This does sound trivial but it’s easy to get the size and fit wrong, especially with online purchasing.^{[2]
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Think carefully about what color you want. Consider what would suit your personal style and also what you have in your wardrobe that complement them nicely.^{[3]
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- Like many things, high tops are at their best in simplicity. Black is the best and safest bet for both men and women, like a pair of Reebok Classic Black Hightops. Remember that black basically goes with everything. The next best choice is white or another block color, like red, navy, etc.
- Small injections of color can be fun; you want what you wear to reflect your personality. But keep such injections of color small or limited to one color. If you’re thinking of going for a bright block color, the success of the look depends entirely on your surrounding outfit.
- If you are looking at the pair of sneakers that look like Skittles, pause for a minute. You might like the color, but you should also think about whether or not that color suits you, fits with your wardrobe, and is something you can and will wear for months. Novelty colors are fun and can look great, but they can also get tiresome.

Part 2

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Wearing High Tops

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Wear skinny jeans with high tops. This is a great look and very contemporary - and it works for both men and women, since skinny jeans are popular for both! Be smart in pairing your skinny jeans or other skinny pants or tights with sneakers. For example, if you're wearing black jeans, wear colored high tops. If you're wearing colorful jeans, maybe go for a more subtle shoe choice.
- As a general rule, don't wear converse the same color as your jeans (unless they're both black because black is a classic and basic shade).^{[4]
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- This look really highlights the shoes and accents the lower half of your outfit.
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Wear pants with wider legs if pairing with thin high tops. Dress your Converse or similar thin sneaker with pants that are wide at the bottom or allow for a peek of skin to pop out between the pants and shoes – this will keep your body proportions feeling right. This outfit is a great option for most women!^{[5]
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- For men, however, pairing baggy pants with high tops is a strict no-no. Wearing baggy paints with high tops creates a bulky look and makes men look clumsy and unkempt instead of cool and stylish. Instead, men should pair their high tops with a pair of casual straight or skinny jeans, a cool T-shirt and an open cardigan (preferably the same color as the high tops).^{[6]
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Roll the bottoms of jeans to create a bit of volume to offset the sneakers. This is a nice spring-and-summer look that works for both men and women, given the recent fashion trend of cropped pants.^{[7]
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Jordan Stolch
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Expert Interview. 27 May 2021.}
- Make sure not have any visible socks peeking out.
- Cropping or rolling your pants helps to focus attention on the shoe while purposefully showing a little ankle. This look really only works with clean, smart sneakers of a single color.
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Dress up your sneakers. For women, consider wearing dresses or skirts with high sneakers. This is a great style for women that will highlight your legs and make them look long and lean.
- It's particularly ideal to wear clunkier shoes with skirts or dresses. Because the shoe has weight, it can stand on its own and usually looks best without baggy pants or tights competing with it.
- You may want to avoid dresses or skirts with thin high tops; sometimes this look can be a little dated. Think skater girls, such as Avril Lavigne, circa 2003.
- Wear socks with your high tops
- Men can also dress up their high tops though not perhaps with a skirt in most cases. Instead, a well-fitted trench coat can look very chic and urban-modern with the right high tops. Take care, however, to not end up looking like you're wearing a costume from the film "The Breakfast Club"!^{[8]
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This is especially a good option for men, who may not feel comfortable wearing shorts with sandals in the summertime. For women, pairing shorts with their high top sneakers is super modern and also, again, highlights their figures and great legs!
This is a key component of wearing high tops as a fashion statement. You want to look cool, not like a slob who can't be bothered to tie his or her laces. ^{[9]
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Do I have to wear socks with high tops?

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Yes, it is probably more comfortable to wear socks, and it will prevent blisters as well.

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What clothes go well with white high top sneakers?

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Wear skinny jeans and a vintage tee.

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Can I wear crazy socks with high tops?

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Sure! If you're comfortable then you should be who you are, crazy socks and all.

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Tips

All these steps are just guidelines. You don't have to follow them exactly. The most important thing is that you make your own style and look unique.

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