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How To Wear Derby Shoes With Jeans [8 Tips]

While it may seem like a straightforward combination, it’s one that’s actually pretty easy to go wrong with. It begs the question, can you wear Derby shoes with jeans? 

Derby shoes can be worn with jeans as long as the formality matches. Dark, tapered jeans with minimal distressing look better with Derby shoes because they’re less likely to look too casual. Suede and brogue Derby shoes often work well with jeans, simply because they look more casual. 

Although that’s the gist, let’s dig deeper. 

Here are some tips you should follow to make sure you wear Derby shoes with jeans in the most effective way possible, each and every time. 

Derby shoes and jeans
Image From Deposit Photos

1. Make Sure It’s Appropriate 

There will definitely be times when a pair of Derby shoes and a pair of jeans simply won’t be appropriate. 

Jeans are a staple of casualwear and should never be worn for business-casual, business-professional, cocktail, or formal attire. 

While Derby shoes may be absolutely perfect in those outfits, a pair of jeans would look entirely out of place. 

In addition, Derby shoes would look awkward when worn to very casual settings. It’s possible to wear Derby shoes with casual items of clothing, but it may look out of place when you’re wearing a vest or hooded sweatshirt up top. 

The Derby shoes and jeans combination works best for smart-casual settings. The Derby shoes bring the smart while the jeans bring the casual. 

wingtip derby shoes
Light brown wingtip Derby shoes. A reasonable choice when wearing jeans because they’re relatively casual-looking

Image From Deposit Photos

Smart casual settings could include garden parties, dinners at mid-level restaurants, first dates, and nights out. 

Items that pair well with jeans and Derby shoes in smart casual outfits include polo shirts, Henley shirts, Oxford shirts, and sports coats. 

You’ve definitely got options, but it’s important to pair the right pair of Derby shoes with the right pair of jeans. 

The rest of the tips on this list will focus on teaching you how to do just that. 

2. Avoid Excessive Distressing

When you’re wearing Derby shoes, avoid distressed jeans. 

The main problem people can have when wearing Derby shoes with jeans comes down to the fact that you’re combining a dress shoe (i.e formal shoe) with casual pants. 

It’s possible, but it needs to be done the right way. 

The risk is that the Derby shoes look too formal for the jeans. The way to avoid this is to choose a more “formal” looking pair of jeans and a more “casual” looking pair of Derby shoes. 

This way, they meet somewhere in the middle. 

When choosing a pair of jeans to wear with your Derby shoes, avoid jeans with excessive distressing. In other words, avoid those with little rips, tears, frills, and frays. 

Jeans with those sorts of embellishments will always make them look more casual. While that’s fine when you’re wearing sneakers, it’ll usually look awkward when you’re trying to wear dress shoes with those jeans. 

The same goes for stonewashed and acid-washed jeans. It’s a great effect, while it may not be as common as it used to be. 

The jeans get more formal-looking as you go from left to right – darker with less distressing. 

Image From Deposit Photos

But once again, it may make the jeans look too casual for the Derby shoes. 

3. Go For A Tapered Fit

When wearing dress shoes with jeans, it’s important to go for a slimmer, more tapered fit. Avoid baggy jeans with wide-leg fits, bootcuts, or flared jeans. 

Slim-fit jeans will produce the most neutral silhouette, sticking close to the leg without looking too tight. Straight-leg jeans can also work, although aren’t quite as effective. 

It’ll look more formal than baggier jeans. When you’re trying to wear Derby shoes, the more formal those jeans look – the better. 

While it may feel as though this limits your choice quite a lot, it’s important when you’re trying to achieve the most balanced and well-thought-out jeans and Derby shoe combination. 

4. Darker Jeans Are Best

Darker jeans will generally work better than lighter shades when you’re wearing Derby shoes. 

Color is yet another feature that can make an item look more or less casual. 

Darker jeans will always look more formal than lighter jeans. 

Blue is by far the most common color for denim jeans. 

You’ll notice that a dark, deep blue pair of jeans will look more formal than a lighter shade of blue. 

The same goes for other colors as well – the darker they are, the more formal they’ll look. Black and dark grey are also very reasonable options. 

Avoid bold and brightly-colored jeans – these will always look more casual. In general, they’ll look too colorful and attention-grabbing for the Derby shoe. 

Sticking to a dark pair of jeans with a tapered fit and minimal distressing will give you the best chance at matching the formality of the jeans to the Derby shoes. 

5. Spectators Work Well

Spectator shoes are a great option when wearing jeans because of how casual they look. 

We’ve talked about how you can choose a more “formal” looking pair of jeans. The next few tips will focus on how to make a pair of Derby shoes look more “casual”. 

It’s important not to forget that both of those options are good ways of syncing the formality of the pants with the shoes. 

Derby shoes come in a variety of forms. While they should always be considered a more “formal” style of shoe, there are definitely some that look more casual than others. 

The lighter, brighter, and bolder the color of the Derby shoes, the more casual they’ll look. 

Avoid dark brown and black Derby shoes when wearing jeans as they’ll always look too formal. 

Lighter shades of brown such as tan brown could work. 

But don’t be afraid to experiment with color. 

Spectator shoes are those where the toe cap and heel cap are a completely different color to the main body of the shoe. You’re left with a “two-toned” shoe – it’s an eye-catching and very casual feature. 

They often work well with jeans for that very reason. 

In fact, as an example, here’s a pair of wingtip Derby shoes that are actually three-toned spectators on Amazon.

It’s easy to find spectator Derby shoes and they’re definitely worth trying if you’re keen on wearing a pair that’s casual enough to combine well with jeans. 

6. Go For Brogue

“Brogue” shoes are those with decorative perforations (i.e tiny little holes in a distinctive pattern). 

While you can get them with many types of dress shoes, it’s common to find Derby shoes with brogue patterns. 

Quarter brogue shoes are where the horizontal edge of the toe cap is lined with perforations. 

Semi-brogue shoes have the toe cap lined as well, but also usually have a “medallion”. This is a fancy, spiraling pattern of perforations on the toe cap itself. 

Full brogue shoes (a.k.a wingtips) have a W-shaped toe cap with perforations lining its edges. They also have perforations lining the edges of the quarters on the sides in addition to a medallion on the toe cap itself. 

The more brogue-ing you’ve got, the more casual those Derby shoes will look. 

When you’re wearing jeans, you’ve got a huge amount of choice when it comes to brogue shoes. 

Often, the more brogue the better. 

Wingtip (full brogue) Derby shoes are a great choice – they’re fun and casual. But why not take things a step further with wingtip spectator Derby shoes? 

The options really are endless – that’s the great thing about wearing jeans. 

While those wingtip spectator shoes would never be worn with a formal suit, they’re perfectly suited to casual pants like jeans and even chinos. 

7. Suede Works Great

While Derby shoes can come in a variety of materials, the most common types of leather you’ll find them in are calfskin, cowhide, and suede. 

Suede has a naturally casual appearance to it due to its lack of sheen, as well as its napped texture. 

Suede Derby shoes are a great choice when wearing jeans for this reason alone. It looks more casual than shinier grains of leather like calfskin. 

While suede isn’t all that easy to maintain, suede Derbys are an excellent item to have in your wardrobe, simply because of how versatile they are when it comes to smart casual outfits. 

Denim has a rugged texture, just like suede does. This is a key reason why jeans and suede Derby shoes (or any suede dress shoe for that matter) work well together. 

While shinier grains of leather can still work (as long as you’re sticking to the earlier tips in this list), there’s just more of a risk that they’ll come across too formal. 

So, wherever possible, go for suede. 

8. Try Changing The Laces

This final tip may not be for everyone, but it’s an underrated method of making any pair of dress shoes look more casual. 

Derby shoes are no exception. 

You may already have a pair of Derby shoes that you want to wear with jeans, but you feel as though the shoes look a little too formal. 

A less expensive alternative to buying a separate, more casual-looking pair of Derby shoes would be to try switching up the laces. 

Changing the laces of your Derby shoes to a nicely contrasting color will make them stand out more. 

It’ll usually make them look more casual, but it’s important to do it in a tasteful way – nothing too crazy. 

While it may seem time-consuming, you won’t need to do it that often. Plus, once you get the hang of it, it becomes (kind of) fun. 

It’s one to try if you think it sounds interesting. 

This tip, as well as the others on this list, are important when you want to get this combination right. 

Derby shoes and jeans can work as a combination and work well, but it’s important to do it the right way. 

Enjoy.