The Best Wingtip Shoes for Work, Weddings, and Everywhere Else

Wingtip shoes (a.k.a. brogues) have long reigned as the dressiest option in a stylish guy's footwear arsenal, but they didn't start out that way. The boss-level shoes were the old-timey equivalent of hikers, crafted from untanned hides so they could handle forest strolls, hunting, and other outdoor-bro activities of the Downton Abbey era. At that time the holes served a purpose: to help water drain from the shoes after trudging through wet terrain. Today those perforations (known as broguing) are purely decorative, and they're what set wingtips apart from other dress shoes. They telegraph that you appreciate craftsmanship, and sartorial flair, and, perhaps most importantly, that you haven't completely buckled to the casual-ification of menswear (we see you, Silicon Valley). Wingtips turn an average suit into an impressive outfit and they have the power to make jeans feel boss-level. Here are the pairs that will instantly upgrade your footwear game, with more affordable versions below:

4 Reasons We Love wingtip shoes

1. The leather is supple and strong: To Boot New York has been in the business of making trusted footwear for 25 years, and designer Adam Derrick is a specialist in below-the-ankle quality. Derrick starts with first choice, hand-selected calfskin from Italy. This yields shoe uppers (the top of the shoe, not the pill) that are both sturdy and pliable, allowing you to pound the pavement, quite literally, without giving too much and stretching out. Take care of these shoes, and they'll outlast your next car.

2. No detail is glossed over: Wingtip shoes are deceptively intricate shoes, despite being trend-proof wardrobe essentials. To Boot New York's are hand burnished (a fancy way of saying polished till they have a smooth, glossy texture) and tricked out with the intricate design features typical of wingtips, including the small perforated holes and the delicate scalloped edges on the toe, heel, and lace portions of the shoe. (That process is called pinking.)(Thank you wikipedia.)

3. The silhouette is just right: The idealized chef-kiss of a dress shoe is streamlined and tapered at the toe (the rounder the toe and chunkier the sole, the more casual the shoe). You want your foot to look elongated, which makes your silhouette look more elegant. To Boot New York's 'Duke' shoe does just that, but keeps from getting too elfin with a bullnose-shaped toe. It's a look favored by us and some unimpeachable designers (like one whose name rhymes with Fom Tord).

4. The price-per-wear can't be beat: Taking into account a good pair of wingtips can last a decade or more—a.k.a, three pairs of cheaper shoes—then $450 isn't so painful. Especially since you can wear these wingtips anywhere: work, drinks, dates, weddings, parties, literally any day of the week. If it helps, know that in buying from a smaller label like To Boot, you're not paying for the cost of marketing, either. You're getting a $450 shoe that, anywhere else, would cost you a lot more.