The best dress shoes do more than take you from here to there. They say something about your personality and the care you put into your appearance. You’ll have to decide if you want formal shoes to dress up or down based on the occasion. Classic styles like Derbies and Oxfords stay traditional, while double or single strap monk shoes push the boundaries of style.
We reviewed five of the best pairs of men’s dress shoes on the market, including a boot and loafer. We’ve also included a shopping guide to help you find shoes that fit your lifestyle and offer durable comfort.
5 Best Men’s Dress Shoes of 2024
Best Men’s Dress Shoes Overall:
Ace Marks The Captoe Griffin
Calfskin leather and a closed, Oxford lace-up design come together in a handmade shoe that’s comfortable, well-made, and ready for business.
$299 from Acemarks.comBest Men’s Dress Shoes Overall: Ace Marks The Captoe Griffin
Best Waterproof Dress Shoes: Johnston & Murphy XC4 Maddox Cap Toe
Best Monk Strap Dress Shoes: Stacy Adams Desmond Cap Toe Monk Strap Loafer
Best Dress Boots: Thursday Boot Co. Captain
Best Loafer Dress Shoes: G.H. Bass Co. Larson Weejuns
Best Men’s Dress Shoes Overall:
Ace Marks The Captoe Griffin
- Top-quality calfskin leather
- Rubber-studded, non-marking, replaceable leather sole
- Flexible construction for a more comfortable fit
When you think about quality dress shoes, the Griffin’s handmade Italian calfskin leather rises to the top of the list. The top of the line leather is put together with a flexible construction method that allows the shoe to move with the foot for long-term comfort. The construction works well with the closed Oxford lacing system that pulls the leather close to the foot for a snug fit. A cap top adds a touch of personality and style.
The Captoe Griffin comes with a high price tag, but these shoes will last more than a single season or two. Each pair is an investment that includes a replaceable leather sole so that the shoe keeps going and getting more comfortable for years. This model comes in five colors, each with a distinct look.
Tip: Properly shining and polishing your shoes maintains the leather’s flexibility and finish. Take the time for a good polish every two or three weeks to keep the shoes in top condition.
Best Waterproof Dress Shoes:
Johnston & Murphy XC4 Maddox Cap Toe
- Made of waterproof full-grain leather
- XC4 waterproof construction
- Interior technology regulates temperature in both hot or cold weather
A walk (or commute) in the rain is enough to ruin a good pair of dress shoes. However, the Johnston & Murphy XC4 Maddox Cap Toe combines waterproof full-grain leather with XC4 waterproof construction that prevents water from coming through the seams and other weak points in the shoe.
With all that waterproofing, moisture stays out. Many waterproof shoes also lock moisture in, for a hot, humid shoe environment that wreaks havoc on the feet. These shoes have a temperature-regulating technology on the shoe’s interior. It keeps the temperature down in the summer and keeps the toes warm in the winter. Lastly, this Derby comes with a removable footbed, that once removed, changes the fit from medium to wide.
Tip: The XC4 Maddox Cap Toe has a contoured insole with cushioning memory foam.
Best Monk Strap Dress Shoes:
Stacy Adams Desmond Cap Toe Monk Strap Loafer
- Single monk strap design
- Flexible upper for a short break-in period
- Well-cushioned insole
Monk straps put a different twist on casual dress shoes. The Stacy Adams Desmond has a single strap design, with the strap over the inset. The strap isn’t the only style feature. A rounded toe cap sets the shoe apart with a quarter brogue embellishment on the toe cap. Heels often get forgotten, but this shoe has a low-stacked heel that provides one more touch of style.
On the inside, the shoe is fully lined with leather and a well-cushioned insole. Some shoes require an extensive break-in time before they feel customized and comfortable. But the Desmond’s flexible upper and cushy insole drastically reduces the break-in time.
Tip: Dress shoes should feel snug without pinching or rubbing. Buy dress shoes in the size that fits snug but not tight. In contrast, running shoes are bought a half to full size bigger than normal but to do so with dress shoes would leave them flopping on your feet.
Best Dress Boots:
Thursday Boot Co. Captain
- Soft, glove leather interior
- Antimicrobial cork insoles
- Goodyear welt construction provides waterproofing but keeps the boots resoleable
A solid dress boot adds attitude and extra foot protection. Each of the Captain’s ten colors and finishes are made of full-grain leather. The outsoles are attached with Goodyear welt construction that seals seams and keeps water out. However, that same design leaves the boot resoleable, extending its life.
The interior is fully lined with soft glove leather. That soft leather helps the shoe adapt to your foot and prevents rubbing and chafing. It’s coupled with a cork insole that molds and adapts to the shape of the foot. Cork is also naturally antimicrobial, preventing any unwanted “friends” from developing in a sweaty shoe.
Tip: Oxford actually describes a closed lacing system (as opposed to an open lacing system) that provides a closer, more formal fit and appearance.
Best Loafer Dress Shoes:
G.H. Bass Co. Larson Weejuns
- Understated matte finish
- Attractive beefroll stitching in the upper
- Comfortable, rounded heel
The Larson Weejuns have been a favorite since the 1930s. While G.H. Bass may have added comfort technology to the insole, these shoes vary little from their previous iterations. Some variations of the Weejuns have a shiny, treated finish, but the Larson’s matte finish gives off a more subtle, understated appearance.
Attractive beefroll stitching in the upper maintains a classic look that comes from the hand-stitching construction process. (It’s called a beefroll stitch because it mimics a piece of beef tied with cooking string.) Last, but certainly not least with this shoe, is a comfortable, rounded heel. Some dress shoes narrow and pinch at the heel, but the Weejuns last (the pattern used to create the shoe) leaves room in the heel to prevent blisters.
Types of Men’s Dress Shoes
| Oxford | Derby |
| The Oxford rose to become a staple in men’s footwear in the 1800s at Oxford University; it’s namesake. This shoe features a closed lacing system. That means that the quarter and facing (portions of the shoe that hold the laces) are stitched under the vamp (the shoe’s upper). Oxfords provide a snug fit that’s generally considered a more formal look. Oxfords can have a wingtip, cap toe, plain toe, or whole cut wherein the vamp is one single piece of leather. If you’re going for one basic multi-purpose shoe, an oxford gives you the ability to dress up or down with a time tested design. | Derbies are based on hunting shoes used in the 1850s. It’s easy to mistake a derby for an Oxford because of their similar shape. In many ways, they’re exactly the same. The only difference is in the quarter and facing of the lacing system. A derby’s lacing system is on top of the vamp rather than underneath it. This design gives Derbies a wider, looser fit than an Oxford. That’s also while they’re considered a more casual shoe. |
| Monk Strap | Loafer |
| Monk strap shoes are secured with either one or two straps and buckles. Occasionally, a three-strap monk shoe comes into fashion, but they’re mostly a fad. While monk straps are considered a casual shoe, they stand out and make a statement, whether worn with jeans or a suit. | The loafer, sometimes called the penny loafer, is the comfortable cousin of dress shoes. It started as a slipper for England’s King George VI but didn’t gain popularity until the 1930s. You can identify a loafer by their raised seam across the toe. They also have a strap, tassel, or slit (into which you could actually store a penny). Loafers range from casual driving shoes to a signature piece to complement a smart business suit. |
| Chelsea Boots | Chukka Boots |
| Chelsea boots fall on the casual side of footwear, but a pair made with high-quality leather may pass on more formal occasions. They don’t have laces or buckles but do have elastic gussets on the sides, so the boot stretches and slips over the foot. | Ankle length Chukka boots are made with only two or three eyelets. Their lack of height and eyelets allows the boot to closely conform to the foot so as not to distort the shape of the pants. At one time, Chukka boots were made of soft suede, but today they’re made in a wide variety of materials for both casual and formal looks. |
What Makes a Good Men’s Dress Shoe?
| Materials | Much of a shoe’s quality comes down to the leather. Full-grain leather creates a higher quality shoe. It’s taken from the top part of the hide and contains the natural grain of the leather. The leather may undergo different treatments to give it a certain color or finish. Less expensive (and less durable) leathers include top grain, genuine leather/corrected leather, and bonded leather. |
| Last | The last is the model that the manufacturer uses to create their shoes. A particular last may have a narrow or wide heel or a more rounded toe. If you find a brand that you like, it’s probably due in part to the fact that the last better resembles your foot. That may mean a certain brand fits you better than others. |
| Outsole | The outsole or sole gives the shoe it’s traction. Dress shoes come in a wide variety of sole types, including leather, rubber, button injected leather, natural crepe, and commando rubber. Leather soles used to be standard, but they wear out relatively quickly, and they can be pricey. However, they’re also typically used on shoes in which you can replace the sole once it wears out. Considering that you may invest a significant amount of money into a good pair of dress shoes, the option to replace the sole extends the shoe’s life. Plus, you don’t have to break in the upper again. |
| Construction Method | Cemented Soles — Cemented soles, also called glued shoes or bonded soles, have a sole that’s attached with glue. The gluing method is fast and inexpensive. However, the sole cannot be replaced, and the glue isn’t as strong as a stitch. Blake Stitch — The Blake stitch creates an enormously more durable dress shoe than glue or cement. This stitch stays close to the upper, almost hiding the stitches within the sole. It creates a closer fit for a snug, sleek design. These shoes are resoleable. However, it does require a Blake machine, which not every cobbler has. Goodyear Welt — A Goodyear welt creates a waterproof seam. These shoes are incredibly durable and can be resoled. However, some men find them uncomfortable to wear. A Goodyear welt is also expensive to manufacture, so expect to pay more for a shoe constructed with this method. |
Style and Design Features
| Broguing: Brogueing is a series of perforated lines along a shoe’s seam. It offers different styles that add personality to your look, but it doesn’t affect the shoe’s fit. Brogues are categorized as full brogues, semi-brogues, quarter brogues, and longwing brogues based on the seam placement and amount of broguing use. Wingtips: Wingtips are a seam or stitch pattern on the toe that points back toward the ankle. They get mentioned in media and books, but they’re nothing more than a toe style. You can find wingtip Oxfords or Derbies. They’re often associated with formal events, but wingtips now appear on casual shoes, too. Toe Styles: We just mentioned one toe style, wingtips, but there are many. Other popular toe styles include a plain toe, cap toe, medallion, apron toe (like that found on a loafer), and split toe (again, a loafer style). Toe style is mostly a matter of personal preference. The best choice for you is one that fits your style and the occasion. However, the plain toe, cap toe, wingtip, and medallion are found on the more snug fit Oxford and Derbies. You may prefer the wider, more spacious toe of a loafer with an apron toe or split toe. |
Frequently Asked Questions
What kind of dress shoes offer a casual look?
Materials play a role in the casualness of a shoe. For example, patent leather shoes and suede often look more casual than a full-grain leather shoe. Design features like broguing, toe style, and color also influence a shoe’s appropriateness for the occasion. Generally, the closer the shoe’s fit, the more formal it’s considered. That puts classic Oxfords at the top of the list and boots and loafers at the bottom.
How do I take care of leather dress shoes?
Leather shoes need regular waterproofing. Once a month is enough in dry climates, while once a week is needed for wet climates. Next is regular polishing. Leather shoes need monthly polishing to keep a shiny finish. Polish also acts as a conditioner to prevent the shoe from drying out.
Lastly, considering storing your leather shoes with a shoe tree inside. While a shoe tree isn’t absolutely necessary, they can extend the life of your shoes. A shoe tree is a form that fits inside the shoe to maintain its shape. Leather shrinks as it dries, and a shoe tree makes sure to retain the shoe’s fit. Some manufacturers make custom shoe trees for each pair of shoes. Universal shoe trees are another option, though they won’t fit as well as a shoe tree made with the shoe’s last.
Should I use a shoehorn?
Shoehorns protect the back of the shoe as you put your foot in. New shoes, in particular, can be stiff and difficult for the foot to enter. Keep a shoehorn in your closet or by the door, so you can slip into your shoes without wiggling, shifting, or breaking the back of the heels.
Final Advice
Shoes make the outfit, and you’ll never get another chance at a first impression. Whether you want a modern take or a timeless look, there are premium leathers perfect for a black-tie event or job interview. Know your budget, decide on the look you want, and invest in a men’s shoe to last for years.
