9 best men’s dress shoes for every occasion, per style experts

9 best men’s dress shoes for every occasion, per style experts

Sneakers may be acceptable attire just about everywhere nowadays, but a good pair (or pairs) of dress shoes is essential to staying well-dressed.

Like tennis shoes, dress shoes are more versatile and varied than ever. You can easily find a pair that looks good without making your feet sore, and you won’t have to worry about them falling apart if you wear them often or put them through inclement weather.

Whether you want business casual dress shoes for going to the office, formal dress shoes for buttoned-up occasions, on-trend dress shoes for a fun night out or black-tie dress shoes for a seriously classy evening, you’ll find the perfect options right here. These shoes look great with dress pants and chinos, so don’t feel like you have to wear a full suit and tie just to make use of this kind of footwear.

We consulted with men’s fashion experts about which brands and styles of dress shoes are worth your money and organized their recommendations across some of the most popular categories. Turner Allen, a men’s personal stylist, and Jordan Stolch, a celebrity stylist turned personal stylist, shared their favorite picks for you to consider adding to your wardrobe.

Click the section links below to shop by category (although we strongly suggest checking out all of Allen’s and Stolch’s picks — you might be surprised by what you see!).

Best Oxford Dress Shoes

What is an Oxford? Oxfords are the stereotypical dress shoes — the kind that would appear as a little drawing in a dictionary next to the term “dress shoes.” Oxfords are defined by their closed lacing system, in which much of the laces are hidden by the vamp or upper of the shoe.

Aidan Brown Cap Toe Oxford

Men's dress shoes
To Boot New York

These have a toe cap to add a bit of classic flair and come in two colors — brown and black. They’re made in Italy using Italian leather and are your go-to for wearing suits. Just remember to pair them with a matching color belt.

“This style lends itself to every situation that calls for elevated dress shoes over sneakers, and will carry you from the office to formal evenings and beyond,” Stolch said. “The rich chocolate colorway from To Boot New York is a great alternative to dressier black, and perfect for pairing with suits and jeans alike.”

Best Derby Dress Shoes

What is a Derby? Derbies are very similar to Oxfords except for their laces — they use an open lacing system in which the pieces of leather with the eyelets have an open space at the bottom. Like Oxfords, Derbies can have toe caps or not, and they’re well-suited to the same dressy occasions.

Aquatalia Men’s Silvio

Men's dress shoes

Instead of traditional hard and shiny leather, these shoes are made with suede, which gives them a slightly more casual look. Considering many men find it difficult to pair extremely dressy shoes with their outfits, the suede material makes styling these easier and more fun. They’re also available in a navy color if you want a shoe that stands out.

“This suede Aquatalia option is an excellent choice for elevating chinos or jeans in a business casual
work environment, or as an alternative to sneakers for a night out,” Stolch said. “Thanks to the rubber soles and rounded toe shape, it’s as comfortable as it is style-conscious.”

Best Monk Strap Dress Shoes

What is a monk strap? Monk strap shoes, as their name suggests, use leather straps and buckles instead of laces to stay secure on your feet. They can be made with one, two or sometimes three straps, and usually have a more youthful vibe than Oxfords or Derbies.

Magnanni Men’s Harris Leather Double Monk Strap Loafers

Men's dress shoes

This simple and timeless design looks impeccable at friends’ weddings, in the office, at an important meeting or anywhere you want to look your absolute best. They also look great without socks if you want to show off some ankle.

“The buckle enclosure adds personality and charisma to your footwear while maintaining the elegance of a conventional Oxford,” Stolch said. “This double strap option from Maganni features a beautiful brown color gradient with darker dye deposits at both the toe and heel, finished off with a rounded toe cap.”

For a more modern look, Allen recommended these Del Toro loafers. The only downside is they’re not available in many sizes.

Best Loafer Dress Shoes

What is a loafer? Loafers are slip-on shoes that are designed to stay on your feet without the use of elastic straps or laces. Many have a decorative addition on the top, such as tassels, metal rings or a simple leather strap. These are easy to dress up or down, depending on the look you’re going for, and are excellent to have during warmer months.

Ferragamo Moccasin with Gancini Ornament

Men's dress shoes

Available in black, navy, brown and brown suede, these loafers are effortlessly chic. They’re made of 100% leather in Italy and feature a metal Ferragamo decoration on the side. The toe isn’t exactly rounded or boxy — it’s somewhere in between, which gives the shoe a modern look.

“With the most premium materials and attention to exceptional craftsmanship, this shoe is an investment to be worn for years to come,” Stolch said. “The tonal marine blue colorway is sure to be a showstopper in a sea of brown and black dress shoes. Pair it with charcoal suits or your favorite wool trousers and watch as your ensemble is brought to life.”

Best Chelsea Boot Dress Shoes

What is a Chelsea boot? Chelsea boots are strapless and laceless and have panels of stretchy fabric along the sides that provide some flexibility when you put on or take off the boots. These ankle-high boots usually are made with only a few panels of leather, and offer a little protection against the weather while maintaining a dressy look.

R. M. Williams Comfort Craftsman Boot

Men's dress shoes

Complete with a leather lining as well as a leather upper, these boots provide a good deal of protection against puddles — making them a smart choice if you have to dress up on a rainy day. They’re available in six neutral colors (all handsome shades of black and brown) and have non-slip rubber soles that make them convenient for walking around town.

“For a boot that blends timeless style and practical durability, look no further than this iconic Chelsea boot,” Allen said. “Its 1960s design is perfect for both daily wear and special occasions.”

Best Wingtip Dress Shoes

What is a wingtip? Wingtips have a similar construction to Oxfords, with their closed lacing system, only they increase your style points by adding an ornamental design around the edges and toe. The tip of a wingtip shoe has an extra layer of material with perforations in it that come to a point like an ‘M’ or ‘W’ (or a pair of wings).

Ted Baker AMAISS Core Formal Leather Shoe

Men's dress shoes
Ted Baker

Highly polished and made of high-quality leather, these wingtip dress shoes take any outfit to the next level. They’re available in two colors — black and brown — and will develop a handsome patina as you wear them, making them a truly unique part of your wardrobe.

“Wingtip dress shoes have remained relatively unchanged for the last century because as a true menswear staple, they consistently get the job done,” Stolch said. “Style them with jeans, trousers, and even your formal suits, and let the perforated design add character and personality to your ensemble. This sleek pair from Ted Baker features hand-finished burnishing and waxing, creating a one-of-a-kind signature look.”

Best Black Tie Dress Shoes

What is a black tie dress shoe? Black tie dress shoes are typically either Oxfords or loafers, and what sets them apart is the extremely shiny look they get thanks to their patent leather construction. Generally speaking, black tie events call for simple and elegant footwear, which is why our expert recommended these classic Oxford-style shoes.

Gucci Worsh Patent Leather Lace-Up Shoes

Men's dress shoes

The high-polish look of these shoes lets people know you’re feeling fancy. They have a leather lining and padded insole for comfort, and feature Gucci’s double G logo on the heel. A bit flashy without going over the top, which is exactly what you want from a pair of black tie shoes.

“Black tie attire is your excuse to pull out the black patent dress shoes, and nothing showcases unparalleled sophistication quite like this pair from Gucci,” Stolch said. “With the miniature hardware version of their heritage logo feature on the back, your footwear is sure to pull your evening look together with ease.”

Best Sneaker-Style Dress Shoes

What is a Sneaker-style dress shoe? Sneaker-style dress shoes can go one of two ways. Either they combine elements of classical dress shoes with the comforts of sneakers, which is what Cole Haan does with their wingtip sneakers, or they’re simply a dressy-looking pair of (typically leather) sneakers. There aren’t formal rules here, but our experts chose nice-looking sneakers because they tend to be easier to style than the combination sneaker-dress shoe variety.

Koio Capri Sneakers

Men's dress shoes

Made from Italian leather, these sneaker-style dress shoes have tight stitching to improve their water resistance and are fitted with removable OrthoLite Hybrid insoles for extra comfort. These are exactly what you want on the weekends, on casual nights out and at the office.

“A pair of minimal leather sneakers is one of the most versatile shoes you can own,” Allen said. “The low-top Capri sneakers from Koio offer a simplistic design in a huge range of colors to suit any occasion.”

Best Desert Boot Dress Shoes

What is a desert boot? Desert boots, also known as chukka boots, are ankle-high boots with an open lacing system. They’re typically made of suede, although leather is a popular option, too, and they generally have only two sets of eyelets so as not to clutter your look with bulky laces.

Thursday Boot Company Men’s Scout Chukka Boot

Men's dress shoes

Thursday Boot Co. offers this boot in a range of colors and materials, as well as options with raised soles that provide more padding and better traction. The shiny brown and black leather options have a more polished, dressy look that adds a bit of intrigue to your formal wear, while the suede options are perfect for more everyday looks.

“Typically more of a casual style, desert boots can easily support formal attire when you know exactly what to look for,” Stolch said. “This pick from Thursday Boot Co. gets the job done perfectly when styled
under suiting, trousers and denim alike. It’s both durable and versatile, and will live up to the demands of long days on your feet.”

Check out the New York Post Shopping section for more content.