How To Wear Dress Shoes Casually? [Useful Tips]

According to psychology, the first thing that most people notice subconsciously in a person is the shoes. Probably that’s why men focus so much on wearing the best possible shoes, eh?

They invest so much time, energy (and money, of course) in selecting the best quality shoes for themselves, whether it be casual or formal shoes.

But here’s the catch: times are changing, and so are men’s fashion trends. Modern fashion is all about fusion and innovation, and the line between what’s formal and what’s casual has been pretty blurred now.

That’s how fashion is supposed to be, right? Ever-evolving, ever changing. So, today, let’s embrace the ever-evolving nature of men’s fashion and learn how leather shoes for men can be worn casually to create amazingly innovative looks!

Who wouldn’t want to utilise the super expensive dress shoes in creating casual, everyday looks?

The following looks combine the eliteness of dress shoes with the simplicity that today’s fashion demands, so you can stay up-to-date with the latest fashion trends and needs. 

How To Wear Dress Shoes Casually?

1. Simple And Stylish Look for Casual Meetups

Business meetings, official dinners, date nights…all of these are occasions for which dress shoes would naturally appear appropriate.

But what if we tell you that leather shoes for men can even be worn at events as casual as a friend’s meetup? How would that look? Trust us, it’ll look absolutely cool and stylish. Let’s see how we can go about such a look!

You can match a polo shirt with denim and a pair of formal shoes to create a look that’s perfect for casual meetups. This may seem a bit unusual (and even tricky) to pull off, but would create the best look if done rightly.

Also Read: Are Converse Business Casual

The key is to select the right polo shirt and pants to pair up with the shoes. The shirt should be perfectly fitted, and so should be the pants, as ill fitted garments would give off an untidy feel with dress shoes. Finish off the look with brown loafers to give it a perfectly casual touch.

Tip: To enhance the look, wear a brown belt with your pants to match with the loafers.

2. Relaxed Look For Official Dinners

The best part about formal shoes is that you can create a variety of different looks with them, based on the type of occasion you’re dressing for.

While a business meeting would definitely require a more primed look, and so we added a suit jacket with it. But let’s say you’re going for dinner with your colleagues, where you’d still want to look proper but a little more relaxed.

So, in this case, instead of wearing a dress suit, you can wear a blazer with jeans and shirt coupled with formal shoes. Since it’s for a more relaxed setting (i.e a dinner), you’d not want to wear a collared shirt but rather a crew neck sweater would be the best choice for this outfit. 

Wearing a blazer would give a chill vibe to your outfit and would not make you look overdressed for an official dinner.

Take special care while choosing the colour of your sweater and blazer. Choose a lighter coloured blazer and a darker coloured shirt, and match the colour of your shirt with that of your shoes to create a perfectly astonishing look.

3. Cool Look For A Date Night

If regular people tend to notice your shoes the first thing about you, then imagine how important it’s for you to wear good shoes on your date night!!! You wouldn’t want to go in front of your potential girlfriend looking improper and boring, right?

You ought to look cool, fashionable and stylish—all at the same time. And voila, our following look will help you do just that!

The best way to impress your girlfriend is to wear a vest over a simple button up shirt and dark blue/black denim.

To tone down your look even more, choose neutral colours for your shirt, such as white. It’d be great if you can find a brown coloured vest because you can then pair it up with brown leather shoes to create a cool look.

4. Casual Office Look

Office is somewhere you’d want to go with a simple yet professional look, not overly dressed up and neither underdressed. The best way to strike this balance is to pair up your dress shoes with jeans and a shirt. 

This will especially come in handy when you have a business meeting, where you’d want to look classy, professional, and sophisticated at the same time. 

To get the perfect look for such occasions, take out any of your suit jackets (preferably black or grey) and pair it up with a plain white collared shirt, straight dark blue jeans and with brown formal shoes. This will create a professional yet casual look, featuring the professionalism conveyed by the dress jacket and shoes and the casualty conveyed by the jeans.

5. Relaxed Look For Summers

How about wearing dress shoes in summers? Say no more! You can very well wear dress shoes in summers to create a perfectly relaxed, airy look. 

Linen shirts are a very common part of men’s summer wardrobes, and creating a super refreshing look by combining a linen shirt with jeans and a pair of loafers would give you a feeling of style and relaxation at the same time.

A white or sky-blue colored linen shirt would look super chic with straight blue denim and brown loafers. The best part about this look is that you can carry it well even at the most casual occasions, such as grabbing a coffee with your pal, or even at casual family functions. 

Tip: enhance your look by wearing a brown leather-strap watch to go with the brown loafers.


Can dress shoes be worn casually?

Yes, the dress shoes can be worn casually when paired with the right outfits and in appropriate settings. The key is to create a balance between formal and casual elements.

Can I wear dress shoes with jeans? 

Yes, the dress shoes can be paired with jeans for a smart-casual look. opt for slim or straight-cut jeans in darker shades for a polished appearance.

What type of socks should I wear with casual dress shoes? 

For a casual look, choose no-show socks or ankle socks that are not visible when wearing your dress shoes. This creates a cleaner and more relaxed appearance.

What occasions are suitable for wearing dress shoes casually? 

Casual dress shoes are appropriate for various occasions, including smart-casual events, dates, informal dinners, and even some workplace settings with a relaxed dress code.


There is a whole separate world of styling possibilities when it comes to dress shoes, especially now that fashion has become crazily innovative. Our 5 ways to wear dress shoes casually will help you utilise your dress shoes in amazing ways, adding a whole lot of style and grace to your upcoming looks.

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