4 Dress Shoes You Can Easily Wear With Khakis

Khakis are incredibly versatile but should be considered “casual” first and foremost. It’s important to be cautious when wearing dress shoes in order to reduce the risk of a formality mismatch. 

So, here are some dress shoe styles you can wear with khakis: 

• Brown Oxford Shoes
• Derby Shoes 
• Monk Strap Shoes
• Loafers

But there’s more to it. 

Certain colors and styles of each of these dress shoes tend to work better with khakis than others. 

Let’s go through each of those styles in more detail, followed by some tips for getting it right each and every time. 

4 Dress Shoe Styles To Wear With Khakis

We’ll go from the most formal/dressy option to the most casual one. 

Oxford Shoes

Oxford shoes can be worn with khakis, with those in shades of brown tending to work best. Black Oxford shoes often look too formal to be worn with khakis. 

Oxfords are generally regarded as the most formal of the mainstream dress shoe styles. This is due to their closed lacing system and their sleek/narrow last. 

They’re the ideal companion to a formal suit or even a dress pants combination. 

While khakis are versatile enough to be worn in business-casual and smart-casual settings, they shouldn’t ever be worn in formal or business-professional environments. 

The main risk here would be that the Oxfords look too formal for the khakis, leading to an awkward and obvious formality mismatch. 

To reduce this risk, try to choose a pair of Oxfords on the more casual end of the spectrum. 

Black Oxfords are as formal as you can get – avoid them altogether. 

Instead, consider a pair in a lighter shade of brown or an even more casual color such as navy or burgundy. 

In addition, you could consider a pair of Oxfords with other casual features such as brogue patterns. 

Nubuck and suede Oxfords will also look more casual than those with a shinier grain of leather. 

To sum that all up, dress down the Oxfords to ensure they don’t look too formal for the khakis. 

Get this part right and there’s no reason why it shouldn’t work. 

Derby Shoes

Derby shoes are a notch more casual than Oxfords and tend to work great with khakis. 

In many ways, both Derby shoes and khakis epitomize the smart-casual aesthetic. 

The reason Derby shoes look a little less formal than Oxfords is that they have an open lacing system formed by the stitching of quarters onto the vamp. 

They’re roomier and more comfortable to wear. 

Because of their more casual appearance, there’s less risk of a formality mismatch with khakis than there would be with Oxfords. 

As a result, you’ve got more choices when it comes to color. 

You could go for a pair of black Derby shoes if you wanted – they would probably look fine. 

Having said that, brown Derbys tend to look better with khakis, simply because khaki is a pale shade of brown in itself. 

As with Oxfords, consider Derby shoes in suede/nubuck or those with brogue patterns if you want to dress them down further. 

“Spectator” shoes are those that come in two contrasting colors, with the toe cap and heel cap usually being a completely different color from the main body. 

It’s pretty easy to find Derby spectator shoes. 

They’re not everyone’s favorite style but do have an immediately eye-catching and casual appearance to them. They tend to look great with khakis if you were looking to make more of a statement. 

Monk Strap Shoes

Monk strap shoes look great with khakis as they both fall firmly within the business-casual and smart-casual spectrum. 

Monk straps are a notch more casual than Derby shoes, although some may argue that they’re pretty level-pegged. 

They’re laceless and are instead secured by the presence of one or more buckles and straps. 

“Double monk straps” are very commonly found and are constructed using two straps on the vamp to secure the shoe. 

They’re incredibly easy to wear with khakis and – much like Derby shoes – tend to work best in brown here. 

It’s also easy to find monk straps with brogue patterns, as well as those in suede. 

Loafers

Loafers are considered the most casual style of dress shoe and are very easy to pair with khakis. 

In general, it’s best to avoid the combination in business-casual settings and reserve it for smart-casual environments where there’s less of a risk of underdressing. 

A loafers and khakis combination usually wouldn’t be formal enough to wear in a truly business-casual setting, simply because of the low-cut, laceless, and ankle-exposing appearance of the loafers. 

You’ll usually be going sockless or (ideally) wearing a pair of no-show socks. 

Consider cuffing the khakis to expose more of the ankle and really embrace the smart-casual aesthetic. 

There are different styles of loafer, with bit (a.k.a Gucci) loafers being the dressiest style. They feature a prominent horsebit-shaped metal buckle on the vamp. 

Penny loafers and tassel loafers are more casual but still perfectly appropriate in smart-casual settings and work great with khakis. 

As with the other dress shoe styles in this list, it’s very common to find loafers in more napped textures such as suede. 

As you’d expect, a pair of brown suede loafers will always look more casual than a pair of black leather loafers. 

Either way, any loafer style or color would usually be perfectly appropriate to wear with khakis. 

To keep things subtle and understated, however, go for a more traditional color such as black or brown. 

4 Tips For Wearing Dress Shoes With Khakis

Here are some tips for wearing dress shoes with khakis in the most effective way possible. 

Brown Shoes Usually Work Best

Brown dress shoes usually look better with khakis than black ones do. The reason for this is that khaki is a light shade of brown and tends to sync well with shoes in other shades of brown. 

This isn’t to say that black shoes can’t be worn with khakis. On the contrary, it can look great. 

But you’ve just got to be more careful when wearing black dress shoes as there’s more of a risk of a formality mismatch. It’s more likely that a pair of black dress shoes will look too formal to wear with khakis. 

That’s why you should avoid black Oxfords altogether. 

More casual dress shoe styles such as Derbys, monk straps, and loafers can be worn in black, but note that the contrast between the khakis and the black shoes will be more striking. 

If you’d prefer a more subtle and harmonious combination, wear khakis with brown shoes instead. 

When dressing your combination up, consider a pair in a darker shade of brown. When dressing down a little more, consider a pair in a lighter shade of brown such as tan or caramel. 

Consider Brogue Dress Shoes

“Brogue” shoes are those with tiny little punctures (perforations) along the edges in a decorative pattern.

You can technically find brogue patterns in any style of shoe, but it’s more common to find them in Oxfords, Derbys, and monk straps. 

Brogue shoes can be “full brogue”, “semi-brogue”, or “quarter-brogue”, depending on the extent to which these perforations are present. 

In short, the more brogue-ing you’ve got, the more eye-catching and casual the dress shoe will typically look. 

Caption – Brown full-brogue “wingtip” Derby shoes

In short, the more brogue-ing you’ve got, the more eye-catching and casual the dress shoe will typically look. 

If you were ever worried about dress shoes looking too formal for your specific pair of khakis, going for a pair with a brogue pattern is a good way to reduce this risk. 

In general, brogue shoes look great with khakis, regardless of whether they’re Oxfords, Derbys, or monk straps. 

Consider Napped Textures

Dress shoes made from more rugged and napped textures such as suede and nubuck work great with khakis. This is because khakis are made from chino cloth which has quite a napped texture to it in itself. 

Another reason is that textures such as suede and nubuck have a more casual appearance to them than shinier grains of leather. 

It’s yet another way of reducing the risk of a formality mismatch between dress shoes and khakis. 

That’s not to say you can’t wear shinier grains of leather – you definitely can. You just have to be a little more careful. 

A pair of Oxford shoes in a shiny grain of leather would often be more appropriate to wear with a 2-piece suit, especially if they’re in a dark color. 

In contrast, a pair of suede Oxfords would usually look perfectly fine with a pair of khakis. The two items blend well together, to the point where the combination wouldn’t draw any unwanted attention at all. 

Go For Socks In A Shade Of Brown

When wearing khakis and any style of dress shoe, go for socks in a shade of brown. In general, it’s best to wear socks that match the pants. 

While this general principle is usually more important in formal attire, it’s good practice to apply it to business casual and smart-casual attire as well. 

The two items don’t need to match exactly, but the closer they do – the better. 

As mentioned earlier, khaki is a light and pale shade of brown. So, consider a pair of socks in a similarly light shade of brown such as khaki, tan, or light taupe. 

Conclusion 

Dress shoes can be worn with khakis in business-casual and smart-casual settings. Brown Derby shoes, monk straps, and loafers would usually be the best options, with those in suede or with brogue patterns working especially well. 

The main aim should be reducing the risk of a formality mismatch. Avoid black Oxford shoes altogether as they’ll most likely look too formal to wear with khakis. 

Enjoy.