In many ways, your accessories say more about you or who you want to be, than your actual clothes do.
This is especially so in formal and professional contexts since men’s fashion is pretty straightforward. Formal is either black tie or white tie, while professional wear is almost always a suit.
Accessories are a different story. A guy wearing a bedazzled Rolex wants you to notice him. A man in a solid dark tie is probably more traditional than one in a bright, patterned one.
Dress shoes are the best example since they’re required in every dress code.
Here’s what your pair say about you.
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No shoe says effortless elegance like loafers do. If you’re wearing loafers, you might be the kind of guy whose hair just falls into place beautifully. He’s the kind of guy who doesn’t look like he tries to look good but kind of just does.
And if you come off as caring at all about your appearance, you’re clearly not a show-off about it.
Since loafers come in so many different designs, each tells a slightly different story.
The penny loafer is understatedly elegant. They’re the cardigan of dress shoes. Meanwhile, the horsebit loafer has a jetsetter or resort chic vibe.
Either way, if you’re a loafer guy, you’re probably all about relaxed class.
Oxford guys are traditional and trend-resistant. He might be highly academic or just an old world gent, depending on what he’s wearing his oxfords with.
The cultural associations with this go-to dress shoe go back to the 1800s. It was popularized on the campuses of elite universities and boarding schools, which is how it got its current name.
Wear it with tweed, and those around you might think you’re a tenured professor. With cable-knit, perhaps you’re bookish and highly intelligent. And pair some sleek leather oxfords with a tailored suit; you might just be James Bond.
Overall, the oxford is always relevant whether it’s trending or not.
Derbys are often compared with oxfords. Like the oxford, the derby’s history gives it a certain cultural association. While the former is made for the office, ballrooms, and university campuses, the derby is a workhorse. It’s a gentleman workhorse, but utilitarian nonetheless.
If you’re wearing a derby, you’re as dashing as the oxford guy, but you might be a bit more sporty. You might like to get your hands a little dirty.
Plus, wearing a robust, round-toed, well-brogued derby with jeans and a t-shirt is almost like a dressy work boot.
The derby was either made for an earl’s wide feet, for soldiers of the Napoleonic wars, or for countryside sports. We’re not sure. Regardless, practicality is in its DNA.
4. Monk Strap
Are you wearing monk straps with your suit? Well, you may have a little bit of edge to you. But hey, you’re still a classy gent.
The buckles on a monk strap shoe give it a touch of a heavy metal aesthetic without compromising its formality. This is why monk straps are one of the best dress shoes to wear with jeans.
The more buckles there are, the more metal you look.
By the way, if you are looking for a nice pair of monk strap shoes, feel free to check out our round-up when you’re done here.
5. Wholecut Oxford
Remember, the more minimal a dress shoe is, generally, the more formal it looks. That being the case, the wholecut oxford makes you look like an incredibly dapper, especially formal gentleman.
If you’re wearing a wholecut oxford in a casual or smart casual situation, you’re probably a bit of a fashionista—if not a lot of one.
No one who wears shoes that you need to shoehorn on can pass as not caring about how they look. And hey, if that’s you, that’s a good thing.
The chelsea guy is probably artistic. He might be a painter or sculptor, a poet, a musician, or Bob Dylan (who was both a poet and a musician).
You see a lot of chelsea boots at gallery openings in Manhattan’s or London’s respective Chelsea neighborhoods.
Maybe you were always creative or a rebel at heart, but now you wear a suit to work. No judgment. You’re just being responsible. Still, you can marry both worlds since chelsea boots are equally as appropriate with dress trousers as they are with a leather moto jacket.
7. Opera Pump
The opera pump’s natural habitat is, of course, the opera house—or the grand ballroom. So, if you’re wearing an opera pump, you love life’s finer things and aren’t ashamed. Your nose stays firmly in the air if your standards aren’t met.
Unlike the more understated branch of upper-class mentality, you aren’t afraid of flashing some style. In fact, you might be a bit of a dandy. The opera pump is a lot like the bowtie, but even dandier.
Ever wonder why chukka boots look excellent with a full suit, chinos, and a safari jacket? It’s because it was made for the kind of man who has both of those in his closet: The gentleman adventurer.
He’s the guy with an all oak salon, complete with a vintage chess set, a giant spinning globe, and maybe even trophies on his wall.
If you’re wearing chukkas, you exude an outdoorsy, casual class.
You don’t need to wear a kilt with your brogue shoes but feel free to do so if you have one. The brogue is a celebratory shoe but also a work shoe. Keep in mind that the decorative perforations originated as a way to avoid water logging, originally worn by farmers on the British Isles.
Today, if you’re wearing brogues, you aren’t afraid of a bit of pizzazz. However, you still have comfort in mind, so you’re a little less uptight than those wholecut oxford guys.
10. Venetian Loafers
The Venetian loafer man is the opera pump man but off duty. He’s classy, he loves caviar and cigars, but he’s the weekend whereas the opera pump is the weekday. Though either gent has a hard time telling the difference between the weekend and the weekday, as he’s a man of leisure.
The Venetian loafer is classy but relaxed. It’s the kind of dress shoe that can be worn sockless, after all. It looks at home with a velvet shawl tuxedo while out and about, or with a silk smoking jacket when you’re sipping whiskey on your Chesterfield armchair.
11. Penny Loafers
The penny loafer man is the accessible, classy guy. He’s educated, he has taste, but he won’t rub it in your face. In fact, he sometimes forgets how elegant he is, and he goes out of his way to make you feel like you, and he, are on the same level.
Plus, he fits in at the most casual sports pubs and the fanciest black tie balls.
And just like the guy who wears it, the penny loafer itself just does that. You can wear a beefroll, moccasin-like brown suede penny loafer to the pub and wear a sleek, black penny loafer with a tuxedo.
The wingtip, like the brogue, is a celebratory shoe. If you’re wearing wingtips, it’s likely that you really like to party. You probably like to party in a zoot suit, and you might like jazz or swing music.
Okay, so this guy doesn’t really exist anymore. Well, he does, but he’s a throwback. So, if that’s you, you’re probably a lover of vintage.
Otherwise, you unabashedly love a louder style. Either way, the wingtip guy is here for a good time, and who doesn’t like that?
Which Dress Shoe Is for You?
Are you a traditional oxford guy or a party-loving wingtip man? An adventure-loving chukka wearer?
Personally, I can go from a loafer to an oxford and back again. I save my wholecuts for tuxedo-appropriate occasions.
Of course, this is all in good fun. At the end of the day, you should wear whatever dress shoe makes you happy.
It’s still fascinating to see that for so many designs, their origins and cultural associations still affect how people see them.