Wear Them Right! The Beginner’s Blueprint To Wearing Dress Shoes The Right Way

After you sedulously curated your personal “state-of-the-art” shoe wardrobe, it dawned upon you that your shoes are only half of the equation. Knowing what ensemble to pair it with, is the other half.

Somewhere down the line, you also caught yourself asking questions such as: “Can I pair my Oxfords with denim?”, “Will I get questioned if I wear a suit with a pair of loafers?” These questions have not only left you scratching your head but also added to your angst towards wanting to look good.

If this is your case, then worry no more. We have got your back!

In this blog, we will discuss the various kinds of outfits that pair well with different shoes. The kinds that are complete no-no’s, and iron out the conundrum that you are currently facing.

So, without further ado, let’s jump right into it!



Oxfords have been a staple of men’s dress shoes for eons, and most probably will remain as one in the near future.

How to wear

This timeless classic was originally worn with formal attire. However, the shoe has evolved over the years and become more versatile after its diverse renditions showed up in the market.

Speaking of Black Oxfords. They are a no-brainer as they can be worn with almost every and any outfit making them the most “protean” shoe in your wardrobe.

However, things get a little different if we speak about a pair of Brown Oxford. They go well with a grey, dark brown, or navy suit.

Lastly, the suede. Even though it belongs to the Oxford Family, it does not share its characteristics. Unlike the previous version of Oxfords, these are well suited for casual outfits and can be paired with chinos or denim.



The next contender is a sibling to Oxford with a slight variation in its lacing mechanism, making it less suited for your upmarket formal suits. The difference lies in the lacing being open and attached ‘over’ the vamp.

How to wear

The rules are somewhat the same for derby as for oxfords. There is not much room to explore and expand upon. However, there is a caveat, they are one notch less dressy as compared to Oxfords, which means that you will be committing a “faux pas” if you are thinking about pairing them with a tie or an extremely formal dress.

Pairing them with slim-fit rolled jeans or chinos will be a more PLAUSIBLE choice.




Loafers have become synonymous with the word ‘stylish’ and have gained a lot of appreciation in the shoe market lately. The shoe comes with a host of options and that’s probably the reason behind it becoming a go-to shoe for entrepreneurs in the late 60s. You are not going to regret having them in your arsenal.

How to wear

When speaking about loafers, the kind of material you choose becomes the deciding factor for your outfit. Like, if you chose to go with a leather or faux leather, formals are what you should be thinking about.

Similarly, if suede is what you get swayed by, then, you are in for a treat. You can create a nice, rich look for yourself with the help of these.

As a rule of thumb, a slip-on that adorns tassels can be worn with any business outfit.

Chelsea Boots


Rumour has it, the shoe was invented back in 1850 by Queen Victoria’s shoemaker J-Sparks Hall as an alternative to riding shoes with laces. The shoes’ popularity went through the roof within a short span of time. Their minimal and sleek design is what makes them so desirable as dress shoes. Unlike oxfords and derbies, they are usually made from a single piece of leather.

How to wear

When it comes to finessing them, you first need to know the types that exist. Chelsea boots can be broadly categorized into two main styles.

Firstly, the usual traditional leather Chelsea boots.

Dare not mistake their name for something ordinary. They can be an absolute menace if paired with your A-ranked suits and business outfits. Its sleek and smooth aesthetics are what gives it the edge and help it outperform its contemporaries.

Next are the suede Chelsea boots. You need to be a little meticulous while approaching these shoes. They tend to pair well with casual and smart casual outfits. However, the opposite of it is also very true. They can depreciate the overall look if paired with formal outfits.


The moment you go down the rabbit hole you understand that there is more to it than what meets the eye when it comes to dressing, and we surely cannot unpack all of it into one blog.

The best strategy would be to build your cadence and not get overwhelmed by the information. Build your wardrobe one step at a time and keep at it. The journey to becoming a confident dresser takes time and an eye for detail.

Also, you can run experiments once you have the basics in place which will allow you to constantly spice up your look, keeping it fresh for your next social event or your next big deal!