Oxfords, Monk Straps, and Brogues – oh my!

Navigating your way through the diverse men’s shoe market.

By: Derek Nelson

Photos by: Allie Little

You’ve worn them your whole life. When you were little, you called them “dress shoes”, and your mother made you put them on for special occasions. Other days you were allowed to wear your comfortable Nikes, but at those stuffy adult events— family reunions, anniversary dinners — you’d have to put on an uncomfortable gold-buttoned blazer, starched khakis, and stiff leather shoes that didn’t allow you to run and play like you usually did.

A young man’s natural repugnance towards “dress shoes” can likely be traced to this origin; they remind him of sloppy cheek kisses from great aunts and forced interactions with lousy second cousins. But wearing these shoes regularly is a part of growing up. It’s not admissible to wear sneakers to a client meeting or to an interview on K Street. Even outside of the office, different shoes are needed for a night out or a date exploring brunch menus in Adams Morgan. This might seem daunting at first, but once the men’s shoe market becomes navigable, it becomes fun to explore.

Shoes give you a way to express yourself, and can be an easy way to add flair to your personal style. Gone are the days of leather shoes worn exclusively with khakis and a blazer – here’s a guide to all things “dress shoes” out there, and how to wear them without looking or feeling foolish.


The Basics

Unless you’re trying to look like you walked out of a nineties music video, your clothes are typically going to be fitted on the slimmer side. Therefore, It’s important that your shoes also reflect this style. This means no chunky, square-toed, rubber-soled shoes – you don’t want to be notorious for wearing the equivalent of the Crocs of dress shoes. As a rule, stick to shoes with a slim profile, and a rounded toe. There are of course exceptions to every rule, and rules are meant to be broken, but you have to know them to break them.



Oxfords are the OG leather lace-ups. If you only have one pair of shoes in your closet, this is the style to own. Named for University of Oxford, and identifiable by closed lacing on the vamp (shoelaces fed through eyelet holes hidden underneath the outside of the shoe), these shoes are meant to be simple. Your pair can be cap toed or plain toed, and can come in either brown or black leather. While a suit is perhaps the most appropriate attire for your oxfords, a simple pair can look as good with your tie and briefcase as with a pair of jeans on your way to Malmaison. We recommend investing in a dark brown shade, as they cover nearly the whole spectrum of outfits appropriate with black shoes (save a black suit), but have much more versatility in pairing with blues and lighter gray tones.



Derby shoes are similar in many ways to oxfords; the only technical difference is in the derby’s open lacing on the vamp (shoelaces fed through eyelet holes exposed on top of the shoe). While many styles of derby shoes come in leather, their more casual look lends itself to construction with other materials. For this reason, you’ll often see them in suede, either uniform in color, or in the form of a saddle shoe. When in suede, derby shoes are usually called “bucks”, and they’re finished with a soft rubber sole. This style adds another layer of depth to your wardrobe. Bucks look really good when paired with spring or summer clothing, and are excellent for bridging the gap between formal and casual. When the flowers start to bloom on Healy lawn, put them on with a pair of brightly colored slim-fit chinos and go sockless to really make an impression in these bad boys.

Monk straps


Monk straps are technically the dressiest shoes that you can add to your wardrobe, and look exactly how you would expect them to, with buckled straps replacing laces on the outsides of the shoes. They can come in either single or double-monk varieties, and look truly beautiful when worn with a well-tailored suit. Recently, however, monk straps have reemerged on the fashion scene, worn less frequently with the classic formal attire, and more with dressed-down outfits. It’s a bold move, but you can pair monks with your favorite pair of joggers to stunt on everyone studying at the Lau 2 tables. If you’re seeking safer options, try them with a pair of thick wool trousers, hemmed without a break, and expose a pair of bright socks underneath to show you’re willing to have fun.



Brogues are not technically their own category of shoe, as there are versions that would classify as either oxfords, derbys or monks, depending on the closure. They are separated from their more conservative counterparts by the perforations that decorate the edges (and often toe) of the shoe. The wonderful thing about them is that they allow you to bring some personality into a dressed up outfit without sacrificing taste, and often look more at-home with light-wash jeans than your dark and pristine oxfords. Pay attention to the different kinds, as quarter, semi, full, and longwing brogues are all available in increasing decoration, respectively. Full brogues are usually labeled as “wingtips”, and this is probably the most common version. Grab a pair of light brown wingtips in full-grain pebble leather, throw them on with some jeans, a button-down, and a very slightly undone tie, and you’ll be ready to impress any date you meet for a bite on M Street.



Loafers aren’t just your dad’s dinner shoes anymore. They come in an infinite number of varieties, in all kinds of different suede and leather finishes. Whether you’re looking at penny loafers, buckled loafers, driving moccasins, kiltie loafers, or ultra bold slippers, there are a few considerations to keep in mind when picking your pair. Make sure the vamp is high. This is the region that goes over the top of your foot, and if it doesn’t come up far enough, it means the loafer can’t be worn with suits, and will make your foot look smaller (plus it eliminates the possibility of odor-saving no-show socks). Most of the time, a simple leather pair such as penny loafers will look better with more formal clothing, and slippers are really the only acceptable loafer for tuxedo wear. In all situations, they can be worn with or without socks, just remove your socks if you’re rolling up your pants, and remember driving mocs usually look better when worn sock-free. Loafers allow you to get away with trendier colors and styles than your other shoes, so keep this in mind when picking them out. Some dark penny loafers might be timeless, but this doesn’t mean a green pair should have no place in your shoe rotation.



Chelsea boots are arguably the classiest boot on the men’s shoe market, and have been re-popularized recently with style icons like Kanye West stepping out in them. They’re by no means a new shoe, and have been around since the Victorian era in England. Their elastic sides mean that pulling them on is a breeze, but don’t buy a pair that has too much going on (ultra high heels or a glossy finish), as they take away from the elegant simplicity and versatility Chelseas are known for. If Bottega Veneta boots like Kanye wears don’t fit into your budget of Wisey’s and Wingos dinners, there are many companies that make them. Just make sure to get a clean leather pair if you’re looking to wear your boots with both a slim-fitting suit and distressed black jeans. Suede and leather are both acceptable and popular, with a battered brown suede pair adding another echelon to your causal shoe collection and a shiny black leather combo allowing you to give a 60s rock-and-roll vibe. The Chelsea is a classic go-to for those just entering the dress boot game.




This is a move for experts only, but a pair of fresh tennis sneakers can replace their formal leather counterparts on occasions when you’re trying to liven up your evening attire. Stick to white if it’s your first time experimenting with this look, and never go with a technical looking sneaker, as this is too busy a replacement. Wearing Adidas Stan Smiths or Converse Jack Purcells (or if you’re not afraid to break the bank, Common Project Achilles Lows) with a suit tells the world that you know how to be a responsible young adult, but the kid is still inside. Just be ready to field any jibes and return them with a smile that shows you have the confidence to pull them off.

Posted by:Thirty Seventh

Georgetown's premier fashion and lifestyle blog.

Leave a Reply

Please log in using one of these methods to post your comment:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s