Wingtip shoes were first known in Great Britain as brogue shoes and can trace their origin to Scotland or Ireland. Originally made of untanned leather, the perforated wingtip design, known as broguing, was functional: it allowed water to drain from the shoe more effectively, making it a working man's show. Today wingtips are widely available in a variety of colors. In the United States, wingtips were traditionally only seen in the office, but today men can wear them for an evening out as well as in more casual situations.
At the Office
In an office setting, wingtips may be worn with a suit or with a blazer, button-down shirt and wool dress slacks. Any business casual attire will work well with wingtips, but remember to harmonize any accessories, such as a belt, with the shoes. For example, if you're wearing a brown leather belt, your shoes should be brown leather.
So many styles of wingtip shoes are available now that these shoes can easily make the transition from office to after hours. Shed the jacket or sports coat you wore to the office and keep the shoes for a dressed-down but fashionable look for cocktails or dinner. Dress slacks with a striped, collared shirt and merino wool sweater are a classic look for wingtips.
If you're wondering how casual you can go and still wear the wingtips, khakis and other casual slacks are okay, but jeans aren't, unless you've acquired a pair of wingtip sneakers with which to experiment. If you want to stay with more traditional wingtips, however, keep your look classic, even as you go casual. A button-down shirt with wool or wool-blend pants says classy but casual and ready for some fun.
What Not to Wear
Because wingtips are semi-formal shoes, it's not appropriate to wear them with a tuxedo or to any occasion at which formal attire is required, such as a black tie event. Likewise, wingtips won't go well with overly casual clothes, such as cargo pants or shorts.
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