The Best Dressed-Up Shoes For Men

Best Costume Shoes (Oxfords, loafers, brogues and derby shoes) may seem formal but don’t need to be uncomfortable; choosing one of these styles will have you looking your best at any formal affair.

Jonathan Evans serves as Style Director at Esquire magazine and covers fashion and grooming issues for male readers. Based in Brooklyn with his wife and son, Jonathan enjoys sharing all things fashion-related.

1. Oxfords

Dress shoes are an integral component of a man’s wardrobe; whether they make you the center of an evening reception, or provide the foundation of his business attire – knowing the difference between an Oxford and other types is vital for his style and image.

Smooth Oxfords feature no seams around the toe area, while wingtip Oxfords feature an M-shaped toe cap for added style. Both styles can be worn to formal events as well as traditional business-dress offices.

Oxford shoe styles feature closed lacing that makes them more formal than Derby shoes, yet still work well with jeans and other smart casual outfits. If you want to reduce formality further, look for pairs without much decoration such as half or quarter brogue Oxfords.

2. Brogues

Perforations on brogues were once designed to drain water away from sodden country boots; nowadays, their perforations serve as an eye-catching design feature. Ideal for both smarter dress shoes as well as more casual occasions like jeans and suit jackets, brogues can make an elegant and timeless choice!

Full brogues (commonly referred to as “wingtips”) feature toe caps with “m”-shaped extensions on either side of the shoe and appear like wings when seen from above; half brogues, however, offer less decorative patterns and feature serrations around its visible edges and medallion in its center; austerity brogues offer similar styling but without toe cap detailing.

3. Loafers

Loafers provide the ideal slip-on shoe, offering both comfort and smarter style than sandals or boat shoes – making them a smart option for semi-formal occasions as well as business casual wear.

Moccasins or penny loafers, these shoes often referred to as moccasins or penny loafers, lack laces and can feature various decorations on their vamp, such as tassels or horse bit designs. Moccasins/penny loafers typically pair well with jeans and t-shirt for a relaxed look, yet can also be dressed up by adding chinos or suit trousers.

Loafers pair well with oversized cable knit sweaters, vintage jeans and leather trench coats for brunch dates. Depending on their design, loafers may even be worn without socks in warmer climates – though we do advise against that option!

4. Slip-Ons

Liv Schreiber has made these backless lace-up sneakers one of her go-to choices, as they offer the classic silhouette without the laborious task of lacing and unlacing. These chic kicks would look equally at home at an art gallery opening as well as with crisp white jeans and an oversized cashmere sweater.

Fashion stylist Liz Teich considers these slip-ons the most comfortable footwear of all time and podiatrist Dr. Timothy Oldani suggests them for nurses and operating room workers to relieve pressure on their feet. Made of sturdy suede material with closed heel design makes these clogs versatile enough to wear for any event or special occasion. Olivia Muenter is a freelance writer and co-host of Bad on Paper Podcast; in writing this piece she consulted celebrity stylist Liv Schreiber, fashion and personal stylist Emily Loftiss as well as Holly Katz of Style Crimes Podcast as well as podiatrist Dr Timothy Olliverioldani DPM FACFAS for advice.

5. Derbys

Although its exact origin remains disputed, the Derby shoe has long been recognized as an appropriate option for smart-casual settings and wider feet. Although its creator remains uncertain, many consider Gebhard Leberecht von Blucher from Prussia to be its inventor.

Suede Derby shoes are an ideal casual option that work well with jeans, chinos and unstructured blazers. For something more sophisticated, leather Derbys featuring Goodyear welting with visible storm welting may be more suitable. Grenson makes stunning dress Derbys that pair well with tailored suits; their casual model can also pair nicely with denim and khakis.