How to wear wingtip shoes to the office

I think wingtip and brogue shoes are a little misunderstood. It can be hard to know if they are dressy or casual or somewhere in between. Therefore, we tend to lean towards the more familiar options at the shoe store, leaving many of these beautiful shoes left behind on the rack. That’s a shame, because these are cool shoes. But once you own a pair or two, the question then turns to what to wear with wingtip shoes, or your new favorite pair of brogues.

The takeaway is this: these shoes are inherently casual, so wear them with caution when pairing with your everyday suit. But they are great for sportcoats, blazers, and even jeans.

Some background

A wingtip shoe is one where the toecap is extended with “wings” that reach towards the sides of the shoe. Here’s an example. Some wingtip shoes are very bold with a two-tone color palette. And while many wingtip shoes are brogued, having decorative perforations along the edge of the toecap and the sides of the shoe, they certainly don’t need to be. Nevertheless, so long as the toe cap area is winged, you guessed it, it’s a wingtip shoe.

Brogues, on the other hand, are the parent shoe to wingtips and trace their beginnings to Ireland and Scotland. Originally, they were shoes with holes punched all the way through them such that water could flush out when walking through wet country (Ireland can be a little moist sometimes!). Modern brogues don’t sport the thru-holes anymore, but the styling remains.

So, are wingtip and brogue shoes casual?

In a word, yes. They are historically semi-casual dress shoes and with all the detail work they don’t often mesh well with the nice clean lines that we strive for in modern men’s style. They fall somewhere in the middle of casual and dressy.

Should you wear them with suits?

This is a good question and the answer, in my opinion, depends on two things:

• How casual your office/occasion is
• And how “brogued out” your dress shoes are

Brogue dress shoes are a more casual alternative to traditional Oxfords because of those decorative holes and details; they are just a little more busy looking that a nice and clean Oxford aesthetic.

That being said, most offices today aren’t too strict on dress code (at least not when compared to those of the mid-century). If your particular office is a bit conservative, sartorially speaking, then I would play it safe and stick with Oxfords.

On the other hand, if you have a little flexibility, I would suggest wearing a lightly brogued shoe like the one below, and in a darker brown hue to keep it dressy.

When to wear with a sportcoat instead of a suit

So, if you have a big board meeting, you’re probably better off leaving the wingtips in the closet and instead slipping on your favorite pair of well-shined oxfords. But I think that most wingtips are just fine for many of your suits and sportcoats. And out here in the Colorado area, I think they are a nice nod to our more casual frontier attitude and work well for more traditionally dressy occasions than they would on, say, the east coast. Also, the less obvious the wings and the “quieter” the brogue detailing, the more dressy the shoe. Make sense?

However, if you wanted to wear more of a wingtip variety with heavy brogue styling (like in the image below), I think that you should wear them primarily with sporcoats and blazers and not an everyday suit.

One of the more interesting categories of wingtips are “spectator shoes.” These shoes are identified by their two contrasting colors. Typically, the toe and heel caps are made in a darker color than the rest of the shoe, which is something lighter in color. Personally, I think these shoes are the perfect wingtips for Kentucky Derby Day!

Wrap up: what to wear with wingtip shoes

Knowing what to wear with wingtip shoes need not be complicated. Just remember that they aren’t overly dressy, so keep them handy for your semi-casual occasions. And generally speaking, I would stick to your Oxfords while wearing more elegant suits that are either pinstriped, have rope shoulders, or are three-piece in nature.

Also, a pair of wingtips shouldn’t be your go-to dress shoe, and certainly not your first pair of dress shoes. Make sure you own a nice pair of relatively plain oxfords in black and then another pair in brown. Then feel free to add a little diversity to your closet with some fun wingtips. And just like any one of your fine dress shoes, take good care of them by using shoe trees.

***

Want to keep riding the shoe train?! Here’s a look inside Ron’s shoe shine box and our guide to the loafer. Also, if you have a wedding coming up, here are some recommendations on footwear.