Comfortable shoes

How to Wear High-Top Sneakers

Jane Bertin
By Jane Bertin. Updated: August 3, 2020
How to Wear High-Top Sneakers

You don't have to be really into fashion to have heard about Air Jordans, Chuck Taylor All-Stars, Nike Air Forces and even newer high-profile models like Kanye West's Yeezys. High-top sneakers have been hugely popular since the 60s, and they have become even trendier in the latest years with the rise of athleisure.

There are many types of high-top sneaker: some of them are bulky, others are thin, some need to be tied, some don't. To help you style your high-tops for different occasions, in this oneHOWTO article we'll go over how to wear high-top sneakers.

You may also be interested in: What Shoes to Wear with a Jumpsuit
  1. How to wear high-top sneakers with skinny jeans
  2. How to wear high-top sneakers with shorts, skirts and dresses
  3. What tops to wear with high-top sneakers
  4. How to wear high-top wedge sneakers
  5. What socks to wear with high-top sneakers

How to wear high-top sneakers with skinny jeans

If you don't know much about styling and combining clothes and shoes, wearing high-tops with skinny jeans is the safest choice, and the easiest way to get a casual chic look. As a general rule, the best way to match colors are the following:

  • Neutral high-tops: Wear them with any trousers you want, but make sure they're not the same color or it will make an awkward impression. Your feet should be clearly differentiated from your legs. White high-tops and classic dark jeans can never go wrong.
  • Two-toned high-tops: One of the colors of the sneakers should match an item of your outfit. You can also match fabrics, such as a two-toned high-tops with leather accent with leather leggings or a leather jackets.
  • Colorful high-tops: Since these sneakers will catch everyone's attention, wear them with classic, dark or steel gray jeans.

When you wear high-top sneakers with skinny jeans, you should roll the hems up or crop them. Showing the ankles is not only a trend, but a trick to balance your proportions visually. Very skinny jeans can be tucked into chunky high-tops, but you should still avoid wrinkles and pools of fabric. Of course, the same applies to long jumpsuits.

You can wear boot-cut or wide-legged jeans if you are wearing thin high-tops, such as Chuck Taylors. However, you should still pinroll or crop them.

How to Wear High-Top Sneakers - How to wear high-top sneakers with skinny jeans

How to wear high-top sneakers with shorts, skirts and dresses

Of course, you can wear high-top sneakers with chino shorts - but you can wear virtually any type of shoes with that. In general, high-tops look better with short items above the knee, rather than with low hemlines, as Rihanna knows well.

Wearing thin high-tops with short skirts and dresses was very popular in pop punk and skater circles some years ago, but if you look at current trends and celebrities you see that they choose chunky sneakers instead to balance out the volume.

You can wear high-tops with long skirts and layered outfits, but it is riskier and you have to have lots of flair and confidence to pull them off - as Zendaya does every once in a while. The middle ground between that and the basic version is to try mid-calf items, such as midi skirts and culottes, with thin high-top sneakers.

How to Wear High-Top Sneakers - How to wear high-top sneakers with shorts, skirts and dresses

What tops to wear with high-top sneakers

Most people think of high-tops as informal shoes, but nowadays that is no longer the case, and they can be seen in business meetings and runways. In fact, the level of formality of the outfit is decided not so much by the kind of items you wear but by the fabrics and materials they're made of.

  • Informal event: To go buy groceries or an afternoon out with friends, wear your high-tops with a neutral or subdued graphic t-shirt. Choose a looser shirt rather than a tight one, and do not tuck it into your trousers or skirt.
  • Semi-formal event: To a date or a low-key meeting, wear your high-tops with skinny neutral jeans and a blazer, with a dress shirt or knit jumper underneath. Converse All-Stars are better for semi-formal events than chunky or loud sneakers, because they are more subtler and they're more of a familiar sight.
  • Artsy event: To a gallery opening or movie premier, you can dare to wear the latest high-tech or design high-top sneakers with long layers, including capes, flowing skirts and sweaters wrapped around your waist. Go all or nothing!

As for the colors, go for white or neutral with a colorful accent. The accent does not necessarily have to match your high-tops, but it can be of its complementary color. Patterns, like stripes, damasks or plaid, should only be worn with neutral or subtle two-toned high-tops.

How to wear high-top wedge sneakers

High-top wedge sneakers look like normal high-tops, except that they have a hidden heel inside. If you're looking for a comfortable way to wear heels - either to add height, to change your silhouette or just because you love them - wedge sneakers are the perfect option for you. Think Beyoncé in the "Love On Top" music video!

These sneakers look like the more bulky high-tops, not like thin ones, although there are wedge shoes with less volume that will look better on people with bigger feet. If you want to wear platform sneakers, the advice still applies.

  • Skinny jeans or leggings: you can either tuck them in or roll them up. They will help to balance out the bulkiness of the wedge sneakers.
  • Shorts, miniskirts or a short dress: you will divide the focus between the top and the bottom of your body.
  • Shirts, tops, sweaters or blazers: tight-fitting tops will focus the attention on your sneakers, while structured, loose or bulky tops will balance the outfit. Up to you! In any case, it's best to choose neutral colors.
How to Wear High-Top Sneakers - How to wear high-top wedge sneakers

What socks to wear with high-top sneakers

In general, most people will tell you not to wear socks at all when you're wearing high-top sneakers.

However, street style trendsetters and fashion designers nowadays will tell you that you can wear socks with high-tops - as long as they're interesting. Roll your trousers up and let frilly, lacy, fishnet or brightly colored socks peek out from the sneakers. The color doesn't have to match the shoe, as long as it's not horribly clashing.

How to Wear High-Top Sneakers - What socks to wear with high-top sneakers

This is how to wear high-top sneakers! Share your outfit tips and ideas in the comments section, and don't miss the following articles:

If you want to read similar articles to How to Wear High-Top Sneakers, we recommend you visit our Fashion & Style category.

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How to Wear High-Top Sneakers