5 Dress Shoe Styles For Every Wardrobe

5 Dress Shoe Styles For Every Wardrobe

Dress shoes come in many different styles, from formal to casual, and somewhere in-between. Since first impressions are everything in this world, for a man to look his very best, whether he’s on a date or at a business meeting, it pays to own a few classic shoes.

Studies show that what you wear on your feet reflects your personality, status, and income. It's common knowledge that one of the first things women notice on a man are his shoes. Though women tend to be a lot more fashion-conscious, men will also show you respect if you’re sporting a beautiful pair. We recommend you put your best foot forward by checking out our list of 5 basic dress shoe styles that we believe every man should have in his wardrobe.

#1 The Oxford

A true classic—the Oxford shoe has a closed lacing system, which makes it the most formal dress shoe you can buy. Why? Because the back of the shoe (the quarter) is stitched underneath the front part of the shoe (the vamp), giving it a cleaner appearance. This shoe is great for job interviews, weddings, funerals, black tie events, and any occasion that demands you look dignified and professional. 

There are different variations of Oxfords you can add to your collection, like Saddle, Wholecut, and Cap-Toe, but the most formal is a pair of Plain Oxfords. However, a Cap-Toe Oxford is the most versatile, and will be the perfect option to start off your collection. Opt for a black or dark color, as lighter colors should be reserved exclusively for less formal wear. The Cap-Toe can be worn to formal events and business casual settings. Any broguing, which are patterns created by punching small holes into leather, would make the Oxford more casual, so keep that in mind.

Shop Anatoly's Black Oxford
Shop Anatoly's Medium Brown Oxford

#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 Derby

#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.

The loafer has a preppy and elegant look that comes in several variations. One popular choice is the Penny Loafer, which has a leather strip sewn across the vamp of the shoe with a cut out pattern. Back when pay phones were common, a penny could be stored in the pocket of the cut out, hence, the name. Additional versions of the loafer include Gucci Loafers, Tassel Loafers, Belgian Loafers, and others. Whether suede or leather, the loafer is great in summer. Pair them with chinos, jeans, and light colored trousers for a tasteful look that will turn heads.

#4 The Monk Strap

double 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 Medium Brown Suede Chelsea Boot


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.

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