Dress shoes come in a range of styles—from formal to casual and everything in between. Because the right pair can shape a first impression, it's worth investing in a few timeless options that elevate how a man presents himself—whether he's heading to a business meeting or a date.
Studies show that your choice of footwear reflects your personality, status, and income. It’s no secret that one of the first things women notice about a man is his shoes. And while women may be more fashion-conscious, men also take notice—and respect a well-dressed peer. That’s why we recommend putting your best foot forward with these five essential dress shoe styles every man should have in his wardrobe.
#1 The Oxford
The Oxford is a true classic. Defined by its closed lacing system—where the quarter is stitched beneath the vamp—it offers the cleanest, most formal silhouette in men’s dress shoes. Ideal for job interviews, weddings, funerals, black-tie events, and any occasion that calls for a dignified and polished appearance, the Oxford is a must-have in any well-rounded wardrobe.
There are several variations to explore, including Saddle, Wholecut, and Cap-Toe styles. The Plain Oxford is the most formal, but the Cap-Toe Oxford strikes the best balance between versatility and elegance—making it the perfect starting point. Stick to black or other dark tones for maximum formality; lighter shades should be reserved for more casual occasions. Keep in mind that any broguing (decorative perforations in the leather) will make the shoe more casual.
Shop Anatoly's Black Medallion Oxfords
Shop Anatoly's Brown Medallion Oxfords
#2 The Derby/Blucher
The Derby, or Blucher, will be your more casual dress shoe. Unlike the Oxford, the Derby has an open lacing system. Since the quarter is sewn on top of the vamp rather than underneath, the lacing remains open from top to bottom, making it easier to put on and take off. In addition, the shoe is built with a rounder profile for added comfort.
Like the Oxford, the Derby comes in multiple different styles and colors, depending on if you’re dressing up or dressing down. Its versatility allows you to wear them with jeans, chinos, and trousers. Perfect for daily wear, the Derby can be worn to the office or at a casual hang out spot with friends. There are very few places you can’t wear it. We recommend you own a brown, full brogue (“wingtip”) Derby for a smart casual look, but you should choose the amount of broguing that matches your personal style.
Shop Anatoly's Cognac Derbies
#3 The Loafer
Imagine a laceless, dress shoe that you can simply slip on and off—that shoe exists, and it’s called the loafer. A cross between a moccasin and a slipper, this style of footwear is comfortable to wear and perfect for travel. It’s not generally considered a formal shoe, but it pairs well with casual suits and sport coats. This shoe has stitching on the vamp that resembles a moccasin, and while it looks like a slipper, it’s not quite one either. The difference lies in its construction: a separate heel and sole make it dressier than a moccasin, and its firmer structure and foot support give it more functionality than an indoor slipper.
#4 The Monk Strap
An early version of the monk strap dates back centuries ago in Europe when monks wore sandals with a strap or two. The modern design may have been inspired by this, as we find the buckle being used on dress shoes beginning in the early 20th century. The monk strap comes in several iterations from one to two to three and even more buckles across the shoe or boot. The straps give the shoe a more fashionable appearance than your regular Oxford or Derby. Hence, the Monk Strap shoe is going to be a more casual dress shoe.
The single monk has been around for much longer than the double monk. However, we believe the double monk strap is the shoe to get, as it has smaller buckles that sit in a more balanced way across the shoe. This variation makes it more fashion-forward, but choose what looks best for you. Buckle positioning can vary between parallel and slightly off-set; we prefer the latter.
Since monk straps are a less formal shoe, reserve it for business casual and smart casual wear. This means you can wear it with your casual suit, sport coat, chinos, and denim. For maximum versatility, pick a dark shade of leather like brown or oxblood.
#5 The Dress Boot
The final shoe style every man should have in his wardrobe is the Dress Boot. You’ll find many beautiful styles in this category of footwear, like the Chukka, Chelsea, and Lace-up. Since each boot differs in its level of formality and utility, you must decide which boot is right for you. For example, the Chelsea is going to be the most formal because it has no lacing system, while the lace-up is going to be the most informal and rugged. The Chukka is perfect for smart casual wear, and due to its open lacing system, straddles the line between casual and slightly formal.
Boots are casual by nature and are fantastic shoes to wear in the winter and fall. Consider a rubber sole if you live in an environment that requires traction. Boots with a good heel will make you look taller, and this is an added bonus when you want to make a good impression. Pairing your boots depends on how dressy they appear. Some lace up boots are elegant enough to be worn with casual suits, for instance. In general, dress boots should not be worn in a formal setting.
Shop Anatoly's Brown Suede Chelsea Boots
I hope you found this dress shoe guide helpful. If you’d like to learn more, feel free to set up an appointment with us at our store in Oakland, CA. We do made-to-order custom shoes for our clients. Please contact us for additional questions.
