Men's Dress Shoes Style Guide
Dress shoes are one of the few menswear pieces that work as hard as they look good. They’re what makes a suit feel finished and a pair of chinos feel intentional. This guide covers the main types of men’s dress shoes, what determines formality, how to think about color, how to style them for different occasions, proper fit, and basic care.
What Determines a Dress Shoe’s Formality?
When it comes to formality, a few traditional guidelines are worth knowing, even as the line between dressed up and dressed down keeps moving.
Closed vs. open lacing. Closed lacing (the eyelet tabs are stitched under the vamp) creates a sleeker, more streamlined silhouette and is traditionally read as more formal. Open lacing, where the tabs sit on top, has a slightly more relaxed look.
Amount of detail. Simpler tends to read as more formal. A plain or cap toe is generally dressier than a shoe with broguing which is the decorative perforations seen on some dress styles.
Sole and toe shape. Sleeker toe shapes and refined soles traditionally skew more formal, while a more substantial sole or a bolder silhouette leans casual. That said, a comfort-driven construction doesn’t make a shoe any less polished. It just means the formality is doing its job without you noticing the effort.
Types of Men’s Dress Shoes Explained
Oxford Shoes
Oxfords are defined by their closed lacing system, which gives them a clean, streamlined profile. They’re traditionally considered among the most formal dress shoe styles, making them a reliable choice for weddings, black-tie-adjacent events, and business settings where tailoring matters.
Derby Shoes
Derbies use an open lacing system, which sets them slightly below Oxfords on the formality scale, though “slightly” is doing a lot of work here. That small difference makes Derbies more versatile day to day: office wear, suits, tailored trousers, and chinos all work.
Monk Strap Shoes
There are no laces and there is just one or two leather straps and a buckle. Monk straps offer a polished alternative to lace-ups and pair naturally with suits, tailored trousers, and elevated separates. They read dressed-up without trying to prove it.
Brogue and Wingtip Shoes
“Brogue” describes the decorative perforations on a shoe, not the construction itself. So a brogue can appear on an Oxford, a Derby, or elsewhere. A wingtip is a specific brogue pattern with a wing-shaped toe design. More broguing generally nudges a shoe toward the casual end, but it’s a nudge, not a rule.
Dress Boots
Dress boots take the refined shapes and materials of a dress shoe and add coverage. Streamlined silhouettes and polished leathers are what separate them from more rugged boot styles, making them a natural fit for fall and winter, or any look where a boot simply works better than a low shoe.
What Color Dress Shoes Should You Wear?
Black is the most traditional choice for formal occasions, and it pairs especially well with black, charcoal, grey, and darker navy suits.
Brown is the more versatile option because it works with navy, blue, grey, earth tones, and more relaxed tailoring. As a general guide, darker brown reads a bit more formal than lighter shades.
Burgundy or oxblood offers a richer alternative to black or brown, and pairs well with navy, charcoal, grey, and other neutrals.
How to Style Men’s Dress Shoes
How to Match Your Shoes and Belt
Coordinating the general color family of your shoes and belt pulls a look together. Black shoes call for a black belt. Brown shoes and belts should complement each other, but they don’t need to be an exact match so a few shades apart still looks considered, not off.
How to Wear Dress Shoes with a Suit
Oxfords, Derbies, monk straps, and other streamlined styles all work with a suit, depending on the occasion. As a general pattern, simpler and sleeker reads more formal, while added detailing relaxes the look slightly.
Can You Wear Dress Shoes Casually?
Yes. Derbies, brogues, loafers, and other versatile dress styles pair easily with chinos, dark denim, button-downs, polos, and knitwear. The one combination worth a second thought is a highly formal Oxford with very casual denim. It's not wrong, exactly, but a bigger contrast than most people are going for. The goal is balance so let the formality of the shoe and the rest of the outfit meet somewhere in the middle.
How Should Dress Shoes Fit?
Dress shoes should feel secure and comfortable. There should be no pinching, no pressure points. There should be enough room for your toes to move naturally, and your heel should stay in place with minimal slipping as you walk. Exact fit varies by silhouette, material, and construction, so it’s worth trying on a few. Wearing a new pair briefly at home before an important event is a smart way to confirm the fit. But a dress shoe shouldn’t require real discomfort to become wearable. If it does, it’s the wrong size.
How to Clean and Care for Dress Shoes
- Wipe down dirt and dust regularly with a soft cloth or brush.
- When color or shine starts to fade, use a polish matched to the leather’s color.
- Condition the leather periodically to keep it supple.
- If your shoes get wet, let them air dry naturally rather than forcing the process.
- Shoe trees help maintain shape between wears.
- Follow any care instructions specific to the shoe’s particular material and construction.
