How to Wear Skinny Jeans: Tips and Outfit Ideas for Men

Simple tips and easy outfit ideas.

Skinny jeans are a super popular style of denim. While we’re seeing a greater acceptance of other styles, such as baggy and flared jeans, skinny jeans are still one of the most popular styles.

It’s no surprise that this is the case, as they look great. These jeans provide the wearer with a slim silhouette that is flattering for some body types. Plus, being cut close to the body makes gives them a more tailored look than smarter than wider styles.

But, if you’re new to these jeans, there can be challenges when working out what to pair them with. Here are some ideas for how men can wear skinny jeans.

How to Wear Skinny Jeans: 5 Tips for Men

1. Choose the Right Type

There are many fits of jeans that fall within the description of skinny jeans. Choosing the right one will get your outfit off to a good start and ensure you are comfortable.

Spray-on jeans are the style that is cut closest to the skin. These jeans are usually made from cotton with a stretchy material such as elastane added. This allows the material to stretch tightly around your skin.

Regular skinny jeans (pictured below) are still often stretchy, but they aren’t cut quite as tightly as spray-on jeans. They are cut closet the body, all the way down the leg and they taper aggressively at the ankles.

Black Uniqlo Skinny Jeans
The Brdwlk

Athletic-fit skinny jeans are made for people with larger legs that are uncomfortable in regular skinny jeans. They have more space around the thighs but still taper in at the ankle. These are for you if you spend a lot of time at the gym.

2. Make Sure the Jeans Fit Properly

Next you want to ensure the jeans fit you. Skinny jeans pose a couple of challenges that make choosing a pair that fits slightly different from buying other pants.

The first issue is that skinny jeans tend to stretch. This means it’s easy to buy a pair of jeans that fit your waist in the shop but soon become too wide. Because of this, I always choose a pair that feels slightly too tight in the shop. I can still button them up without any problem, but I want them to be slightly tighter than I would normally like.

When it comes to length, I like to choose a pair where the material ends just at the top of my shoe. Any longer, and you’ll start to see a build-up of denim that can ruin the jeans’s clean lines. If the denim is slightly too long, then I don’t mind rolling them up in most cases.

Low rise pants shirt t-shirt

The final question is how tight they should be. The jeans should fit close to the skin all the way down your leg. But they should be comfortable and easy to get on. If you find yourself struggling to get the jeans up your leg, maybe choose a larger size or a pair of athletic fit skinny jeans.

3. Choose the Right Color and Style

Now you’ve chosen your fit, it’s time to look at the type of denim you wear. It’s important because while skinny jeans go with many types of outfit, the same pair won’t necessarily look good with both a blazer and a baggy t-shirt.

As a general guide, dark, solid colors with little fading go best with smarter outfits. If you plan to wear your jeans with a shirt or a blazer, perhaps to the office, then look for skinny jeans that match this description.

If you want to wear your jeans with more casual outfits—like t-shirts or denim jackets—then faded pairs or those in lighter colors will look great too. You could even choose a pair with rips and tears.

4. Choose Suitable Footwear

Brown Blazer Blue Shirt Dark Jeans

Skinny jeans go well with plenty of types of shoes and footwear. Our favorite shoes to wear with skinny jeans include canvas shoes, desert boots, and minimalist sneakers.

Personally, I like relatively low-profile shoes and sneakers. But there are plenty of examples of people looking great in bigger shoes like Jordans and work boots. Just a pair you feel comfortable in.

Remember that you can wear jeans with dress shoes. Just stick to darker styles without as much fading or rips.

5. Decide on a Slim or Oversized Sillhouette?

When skinny jeans first became popular, it seemed like most people wore them with other items that fit close to the body. This meant slim-fit shirts, t-shirts, and sweaters were popular pieces. Even coats and jackets tended to be styles like denim jackets, fitted blazers, or leather jackets, that fit close to the body.

In recent years, it’s become just as common to wear skinny jeans with oversized pieces—perhaps as the influence of streetwear grew in fashion. This means larger t-shirts, jackets, and sweaters became just as popular.

This also ties into the above point. If you choose chunkier shoes like workwear or sneakers, then your outfit may look better with an oversized upper. This is a look that Kanye West has nailed down. On the other hand, if you wear a slim-fitting upper, then lower-profile shoes will usually look best.

Skinny Jean Outfit Ideas for Men

Skinny Jeans with a casual Jacket and Boots

Skinny jeans and casual jacket

Skinny jeans, a jacket, and boots is all you need for a stylish outfit that will do you all the way from spring to fall. I like wearing a denim jacket with jeans, but leather jackets, shackets or overshirts look good too.

Skinny Jeans with a Blazer

Skinny jeans and blazer

Skinny jeans are cut close to the body which means they have an almost tailored fit. This means the right pair goes great with smarter pieces like blazers and shirts.

Skinny Jeans with a Shirt

Casual shirts look great with skinny jeans. Flannel shirts and skinny jeans were the hipster uniform for years. But other types of casual shirts will work just as well.

Skinny Jeans with a Sweater

Skinny jeans and sweater

Sweaters and jeans is a simple yet flexible outfit. Choose an oversized sweatshirt with casual sneakers for a casual look, or a knit sweater and shoes for a smarter one.

Skinny Jeans with a T-Shirt

Skinny jeans and t-shirt

A t-shirt and skinny jeans is a simple outfit. Choose an oversized t-shirt for a modern fit or a slimmer cut for a smarter look.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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