Men's Custom Clothing

Dress Tips

What to wear with wingtip shoes

I think wingtip 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 the beautiful wingtip shoes left 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.

Some background

A wingtip shoe is one where the toecap is extended with “wings” that reach towards the sides of the shoe. 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.

Now while we’re on the subject, it’s worthwhile to talk a little bit about brogues, because wingtips descended from them. Brogues trace their beginnings to Ireland and Scotland and 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 is remains.

So, are wingtip shoes casual?

In a word, yes. They are historically a semi-casual dress shoe and with all the detail work (either with or without the brogue detail) 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.

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 oxfords. That being said, 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?

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!

In the image below, we have three examples of a saddle shoe, but only one wingtip. Can you spot it?!

what to wear with wingtip shoes

Wrap up

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.

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!


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