Best Men’s Shoes to Wear with Rolled up Jeans

best shoes for rolled up jeans

What’s the best men’s shoes to wear with rolled up jeans? This is a question a lot of guys ask, as jeans continue to be one of the most popular type of pants for casual wear. Rolling up the cuff of your jeans is a great way to show off your shoes, so you’ll want to wear nice shoes to complete your outfit, but what kind?

What kind of shoes you wear with your rolled-up jeans depends on what type of look you’re going for. If you’re going for a casual look, running shoes or boat shoes are a great option. If you are looking for a sleeker look, boots like Chelsea or chukka boots can make your outfit look more put together. Lastly, if you want a semi-formal look, formal footwear like loafers, derby shoes or oxford shoes will take your jeans to the next level.

If you want to know exactly how to pair these shoes with a rolled up pair of jeans, keep reading!

Casual Look

As jeans are typically worn casually, there are plenty of casual shoes that go well with them. Casual can still look put together, so wearing a slip on shoe like boat shoes can tie your outfit together well, but not make it look formal and stuffy.

To keep the whole outfit even more casual, wearing sneakers with rolled up jeans is a great choice. You can wear a pair of clean, white sneakers to make your outfit pop or a pair of black sneakers to not draw attention away from your outfit.

Both types of shoes are great to wear with rolled up jeans as you don’t need to wear socks with them, further showing off the shoes.

Sleek, Put Together Look

If you want to make your jeans look more put together rather than something you just threw on, boots are a great option.

Boots are not overly formal, keeping your outfit casual, but put together. Chelsea boots or chukka boots are a good option as they are super versatile. Chelsea boots and chukka boots can have a relaxed and rugged appearance or the leather ones will look sleeker.

Pairing a rugged pair of boots is a good choice if your outfit is more rugged and relaxed as well. A sleeker, leather pair will make your outfit more sophisticated and put together, more so when paired with a rolled up pair of dark wash jeans.

Semi-Formal Look

If your work allows it, you may want to wear jeans or go to interviews wearing them. How can you style jeans to still look semi-formal? Wear the right pair of shoes! Shoes like derby and oxford shoes or loafers are great options to keep your outfit semi-formal.

Oxford shoes and derby shoes are a classic pair of formal shoes, typically in brown, burgundy and black to stay formal. Wearing oxford shoes will take your outfit from casual to semi-formal. You can even pair your jeans and oxford or derby shoes with a suit jacket or blazer, making the perfect semi-formal outfit.

Loafers are the ideal way to create a semi-formal, luxurious look. They come in plenty of different designs and styles to ensure that you can inject your personal style into them while still staying semi-formal.

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How to Roll Your Jeans

Once you’ve picked the perfect shoe for your outfit, you need to make sure you have the perfect jeans. All of these looks will pair best with a slim, skinny or regular fit jeans. This will help make your outfit look put together, no matter the style you’re going for.

Rolling up your jeans is also a great way to look put together as it will show off your perfectly picked shoes and make your pants look more fitted. When rolling up your jeans, aim for a cuff that’s about 1 inch to 1 and a half inches wide. Also, never roll the cuff more than twice or the bottom of your pants will be too thick and bulky, likely covering your shoes.

Sperry Men’s Striper II Sneaker

Sperry Men's Striper II Cvo Sneaker, Navy, 11.5

Starting off with a casual shoe to pair with your rolled up jeans is Sperry’s Salt Washed Striper II Sneakers. These classic sneakers will keep you comfortable while still looking stylish.

They come in 22 different colors meaning there’s something for everyone and every outfit! They are made from a breathable canvas material with neat, cotton laces. The sole is made from rubber and is non-marking meaning you can wear them on any type of flooring without worrying about scuffing it.

They provide a secure and structured fit, but are easy to put and take off without untying the laces. The laces are also able to be hidden behind the tongue of the shoes, this will provide a neater look that will better complete your outfit.

Sperry’s sneakers are great for daily wear as they are comfortable with built in arch support and can go with a variety of outfits and jeans.

Sperry Men’s Billfish 3-Eye Boat Shoe

Sperry Mens Billfish 3-Eye Boat Shoe, Grey, 7

Keeping it casual is another Sperry shoe, the Billfish 3-Eye Boat Shoe. Boat shoes or other slip on shoes are a small step up from typical running shoes or sneakers. Boat shoes can keep your outfit casual, but will look more put together than a pair of sneakers.

Sperry is well-known for their boat shoes, so these are a great choice if you’re in the market for a new pair. With 25 different neutral colors available, there are great options for any outfit.

These boat shoes are made with 100% leather, but are still extremely breathable as the upper panels feature an air-mesh material. This means you can wear these boat shoes without socks to better show them and your outfit off with your rolled up jeans.

The leather is not only durable, but is stain and water-resistant, meaning rain or puddles will not destroy your shoes.

Even though they are durable, the laces and design of a boat shoe will keep your outfit looking casual and put together.

Bruno Marc Men’s Suede Leather Chukka Ankle Boots

Bruno Marc Men's Suede Leather Chukka Ankle Boots - to wear with jeans

Moving onto a sleeker outfit look, here are Bruno Marc’s Suede Leather Chukka Ankle Boots. Boots are a great option for either casual or formal wear depending on how you style them.

These chukka boots are easy to style as they are sleek and come in nine different neutral colors to match most outfits. A classic black or tan chukka boot would pull together any outfit with rolled up jeans to make you look sleek and put together.

This pair has a slight heel, approximately 1 inch to give you subtle height. The heel and sole are also durable and comfortable made from synthetic rubber to absorb shock and provide cushion.

These are great daily use shoes due to their versatility and how comfortable they are to wear. Roll up your jeans and throw these on to complete your outfit.

Dream Pairs Modern Oxford Dress Shoes

Bruno ITALY PRINCE Classic Modern Oxford Wingtip Lace Dress Shoes to wear with rolled-up jeans

Moving on to a formal pair of shoes now with Dream Pairs’ Italian Formal Oxford Wingtip shoes. These are a classic pair of dress shoes that will help make your rolled up jeans look more formal.

This pair comes in nine, neutral colors with great black and brown options. Despite oxford shoes being a formal shoe, Dream Pairs’ version is still quite comfortable.

The lining is made with premium faux leather and a latex cushioned footbed to keep your feet comfortable throughout the day. This pair of oxford shoes boasts a small, one inch heel to give you a bit of height.

Dream Pairs’ oxford shoes feature a classic brogue wing tip design with ornamental, perforated patterns on the side. This gives the shoe a classic, formal look.

As oxford shoes are formal, they are best worn with a dark wash jeans so the pants and shoes don’t clash. Wearing a distressed pair of light wash jeans with this classy pair of oxford shoes will be too contrasting. Stick to darker colors to show off both your outfit and oxford shoes.

Cole Haan Men’s Nantucket Loafer

Cole Haan Men's Nantucket Loafer to wear with jeans

We are ending our list of the best men’s shoes to wear with rolled up jeans, with a slightly less formal, but still classy shoe: Cole Haan’s Nantucket Loafer. These are still a great shoe to create a semi-formal outfit, but are not as fancy as the prior oxford shoes.

These particular loafers come in three different colors, but each one has two colors that work well together. Having two different colors on your shoes means you can pair them with more outfits.

For example, this blue and chestnut pair of loafers would pair greatly with a dark wash pair of jeans and any neutral-colored shirt.

This pair of loafers is made with 100% leather which is a great material in formalwear. The rubber sole is great for daily wear as it will absorb shock from constant walking. These shoes are breathable and can be worn without socks to further emphasize your shoes with your rolled up jeans.

Like this content, check out our helpful article on What Kind Of Pants Goes With Chelsea Boots, Best Types of Jeans For Men With No Butt and answers to your questions like Are Khaki Pants Considered Jeans and Are Cargo Pants Considered Jeans?



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