The Black Oxford

The black oxford is an all-time classic, especially in a captoe style. It's a versatile shoe that you can wear for business, formal events, and even funerals. Unlike brown shoes, black comes in a single shade, so you don't need to invest in multiple pairs of black shoes - one high-quality black oxford is a must-have staple.

You can wear a black oxford with two-piece suits, three-piece suits (especially in navy, charcoal, and grey), blazers, and even tuxedos for black-tie or white-tie events. The clean, seamless silhouette of a whole-cut black oxford makes it the most formal option, allowing it to be worn with the most formal ensembles.

The Brown Derby Wingtip

A derby shoe is less formal than an oxford, with an open lacing system that makes it more flexible and comfortable, especially for travel. I recommend a medium brown color, such as the antique brown cognac from Ace Marks, which features hand-polished and hand-burnished leather for a versatile, multi-tonal appearance.

The full brogue detailing on this derby wingtip shoe gives it a more casual character, allowing it to be paired with a wide range of outfits, from suits to corduroys and denim.

The Loafer

The loafer is a slip-on shoe that is inherently casual, yet it remains a timeless classic. Loafers are incredibly versatile, allowing you to dress them up or down with ease. They come in various styles, such as tassel loafers or penny loafers, the latter of which are considered the most classic.

For maximum versatility, I suggest choosing a loafer in a different brown shade than your derby wingtip, perhaps with a reddish undertone. Loafers pair well with everything from seersucker to jeans, but should be avoided with double-breasted suits.

The Double Monk Strap

The double monk strap shoe is a stylish and youthful option that adds a unique flair to your wardrobe. I recommend a reddish-brown color, such as the brandy antique brown from Ace Marks, which features a hand-polished and hand-burnished finish for a dynamic, multi-tonal appearance.

This clean-lined, non-brogued double monk strap can be dressed up with a suit or down with jeans and a casual top. Be sure to pair it with a matching belt for a cohesive, polished look.

The Half Brogue Oxford

The half brogue oxford is an in-between option, less formal than a plain oxford but more refined than a full wingtip derby. This style features a captoe with broguing, as well as a subtle medallion detail, creating a versatile shoe that can be worn with a wide range of outfits.

I recommend a medium brown shade, such as the lighter antique tan from Ace Marks, which is different from the other brown tones in your wardrobe. This half brogue oxford can be worn with suits, tweed, and everything in between, making it a great spring, summer, and fall staple.

By investing in these five essential dress shoe styles - the black oxford, brown derby wingtip, loafer, double monk strap, and half brogue oxford - you'll build an extremely versatile shoe wardrobe that can be mixed and matched with a wide range of outfits. This approach allows you to focus your wardrobe investments on other areas while still maintaining a stylish, well-rounded shoe collection.