How to Wear Brown Wingtip Derby Shoes

For the second article in our series on the first five business shoes to own, we'd like to talk about  a surprisingly versatile shoe- the brown wingtip derby.  In this article, we'll cover what a derby is, what it's not, what a wingtip is, and why the color should be brown. We'll then show you how to style them- and how not to. 

What's a Derby? Why Wear One? 

A derby shoe is any shoe with an open lacing system. In a derby shoe, the laces are fed through holes punched into the quarters, which are then attached to the vamp.

This is converse to an Oxford, which has a closed lacing system in which the laces are fed through holes in the upper. 

Because the laces sit higher and are not, technically, part of the upper, the laces can be opened up more. This works extremely well in ready-to-wear shoes if you have high arches, wider feet, or if your feet swell throughout the day as you walk. Slightly looser fitting shoes can relieve pressure across the vamp and make for a more comfortable ride. 

The Derby style isn't limited to dress shoes. Because they're so easy to take off and put on, most boots come equipped with this lacing system. 

While we're here, let's touch on the subject of bluchers. Bluchers are a variation of the derby style in which the laces are pulled through two pieces of leather attached to the upper- but aren't part of the rear quarter. This makes for a very comfortable and flexible, if informal, shoe. 

What's a Wingtip?

Derbies can come with or without broguing. But, for your first pair, we'd recommend a pair with a brogued wingtip. A wingtip is a style of broguing in which the punches in the leather form a kind of "M" or "U" shape. 

So, why wear wingtips? While this does make the shoe more casual, we think it adds quite a bit of character and visual interest in your footwear. 

Brown? Why Not Black?

While derbies come in all colors and many shades (and a pair of off-white bucks can look very smart at the races!), we believe a medium-to-dark brown pair is going to be the most versatile and the easiest to dress up in a business environment. 

If you're building a shoe wardrobe according to our guidelines, you've already got a black pair. So, it naturally follows brown would be your next move. 

Why medium to dark brown and not tan? While tan shoes can look very nice, the lighter in color they are, the more casual they tend to become. In a business environment, you'll want something a little more formal that you can wear with a variety of outfits. 

How to Style Brown Derby Shoes

We've covered shoe style, ornamentation, and why you should choose brown over black. Now, how should you style them? 

The answer is that brown wingtip derbies are extremely versatile shoes, especially when it comes to business casual. 

Darker brown derbies can be worn with suits, but work really well with more casual suiting options like flannel, hopsack, or cotton. 

Derbies quite easily anchor the "menswear uniform" with grey flannel trousers, white button down, and a navy blazer. 

For a bit of fun, try a plaid or windowpane sports jacket in navy and tan, cream or 'winter white' trousers, and a light merino wool turtleneck of a slightly different shade. 

In this day and age, denim can sometimes be worn to business meetings, as long as it is clean, slim, and properly hemmed. Derbies pair extremely well here not only for business, but for an evening out. 

Wrapping Up

We hope you enjoyed this primer on derby shoes and how to style them. We'd recommend something in a medium-to-dark brown and with a wingtip on the toe. Style them with casual suits, denim, or an odd jacket and trousers. The sky is really the limit here!

Thanks for reading, and if you're interested in a custom pair of shoes, be sure to check out our shop here.