Casual Men Shoes to Wear With Jeans for 2021-With Special Tips

Shoes define who you are. It is often said that a man’s character can be identified by his choice of shoes. They have that compactness that a pair of sandals or flip flops can never have. It is often challenging to surmise what are the casual men shoes to wear with jeans. But I am here to help.

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Jeans are normally what a person looks forward to wearing on weekends. They have a comfort zone and always look great for any casual occasion. And for this sort of versatility, choosing the right pair of casual shoes is very essential. We have come up with this guide to help you in deciding on what are the different types of casual shoes men can wear with jeans.

Casual Men Shoes to Wear with Jeans

Casual Men Shoes to Wear With Jeans

# Chukkas and Cowboy boots:

Wearing these types of shoes with jeans is a bit tricky. If you are not careful with the right type of jeans, you may look hilarious. But if worn well they can be quite the fashion statement.

Chukkas are basically ankle-high leather boots with suede or leather uppers, leather or rubber soles, and open lacing with two or three pairs of eyelets. Cowboy boot is the colloquial name for western boots which is regarded as a characteristic footwear by cowboys. But nowadays this is quite the fashion for men.

casual men shoes to wear with jeans

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  • Try to wear medium and dark wash jeans
  • A slim pair of jeans is a good combination
  • Be careful that the jeans are not too tight
  • If you’re planning to wear chukkas you should roll up your cuffs
  • For cowboy boots wear boot cut jeans and make sure the size is sufficiently long

# Loafers:

Loafers tend to be classy and casual at the same time. They are quite popular nowadays and are worn by men of all ages. And they look grand and are one of the best casual shoes for men with jeans.

When worn, they prove to be extremely comfortable. They curve around the curvature of the leg which makes them flexible too.

  • Jeans can be of any shade
  • Ripped, selvedge and washed jeans are all suitable
  • Distressed pair of jeans is recommended
  • Avoid long or baggy jeans

A shoe has so much more to offer than just to walk

# Ankle Length Canvas Trainers:

These type of shoes are commonly used in parties or any casual event. The primary feature is that these extend till the ankle level.

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Also called Bootie, they can be flat or heeled.

  • Make sure your jeans match the color scheme of the trainers well
  • Also ensure that the Jeans aren’t too long or short, they should sit perfectly on top of the shoe
  • Recommended to insert the jeans into the covering in order to avoid covering the design

# Boat Shoes:

If you’re looking for casual but smart at the same time, then Boat shoes are the perfect match. With them often there is more freedom to experiment with different shapes and materials.

You can wear them office or when you’re travelling. I’d also suggest wearing them on beaches. They blend it nicely are one of the common casual shoes to wear with jeans.

  • Wear with Cuffed jeans. Gives a nautical look.
  • The jeans should skim the tops of your shoes
  • Remember to play to your strengths and find silhouettes and colors that suit you
  • Wear in summer and avoid in winter
  • Refrain wearing them with visible socks

Oxford Shoes:

Oxford shoes also fall in the smart casual category. They include the lacing system where the eyelets are normally located on the quarters.

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Being one of the common shoes that look good with jeans, they make sure you don’t look very dressed up and fit nicely into the outfit of jeans and shoes.

  • Slim-fitting pair of dark-wash jeans
  • Make sure the length of your pants rests just on the top of the shoe
  • Can cuff a little to show off your socks
  • Avoid faded, ripped jeans. These don’t go toe to toe with Oxford shoes.

These shoes are best worn with socks. If you’re interested in combining socks, shoes and pants then you may want to look at this –How To Combine Socks, Shoes & Pants

# Ankle Length Boots:

One of the coolest and best shoes to wear with jeans ever made. Being the men’s casual boots to wear with jeans, they have wide spread fame. Furthermore, they have been worn by celebrities and fashion icons alike and are one of the coolest casual shoes to wear with jeans.

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The Ankle boots have zippers or straps, instead of elastic panels. This makes sure there is a secure fit around the ankle. There are many styles of jeans which go with the many varieties of ankle boots.

  • Generally, look good with tight jeans
  • Wear skinny jeans if the boots have a long shaft. Make sure to tuck in.
  • If you want your jeans untucked or cuffed, then choose the boots with a lower shaft. This gives the chance to show some ankle which overall suits the attire.
  • All in all, if you just want to play safe then go with a jean which is folded or with a ripped jean faded at the tips

Casual vs Dressy Shoe With Jeans:

If you intend to spend your day with friends, party or just going on a picnic trip then you need to go for something casual. Dressy shoes are there for you when you have a meeting or attending an important social event.

Here are some useful tips that you should consider before buying casual shoes.


Shoe Material

  • Check the construction of the shoes
  • Do the materials feel durable? Prone to rough and tear?
  • Ensure the material at the sole is sturdy. That will protect you if you happen to step at a sharp object
  • Avoid thin bottoms

Pick a reputable brand

  • Often famous brands are reliable and offer shoes which have a long life
  • Try the same type of shoe offered by different brands
  • Quality is what matters. Cheap shoes may not offer the same comfort.

The right time

  • If possible, go buy shoes when all your day’s chores are done.
  • In that way, you will account for any expansion (feet tend to enlarge while walking)

Shoe style

  • Various designs can be out there for the same type of shoe
  • Pick the one that matches with most of your outfits


  • Keep in mind the different outfit that will complement your shoe
  • Avoid pure white colors as they tend to show dirt more

Giving a trial

  • It is very necessary to wear your selected shoes before buying
  • Walk around the shop wearing it
  • It is better to be wearing a sock while trying them on o Make sure they feel “right”- comfortable

Online shopping

  • Check if the return shipping is free of cost. In that way you can easily return them if they don’t feel right after delivery.
  • Make a habit of going through the different reviews provided by the previous customers. They will give you an average idea on your desired shoe.
  • The same shoe may be offered in cheaper prices at different websites. Make sure you do your research.


Lastly, I’d like to say that if worn right, you have the power to look great with a pair of jeans and shoes. In any casual event you will blend in perfectly with. So, choose your preferred style from the guidelines provided on casual men shoes to wear with jeans, and never worry again.

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