You know not to wear sneakers to a formal event. Some slip-ons are okay, if they look like fancy loafers. Lace-ups are good, too, unless they look too much like Dr. Martens.
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Men’s dress shoes sit somewhere between these extremes. Sometimes, an oxford is expected. Other times, you can get away with a derby or a Chelsea boot. On many of these footwear choices, brogue details have practically carved out their own niche: The embellished, intricate dress shoe.
To extinguish all the gentlemanly airs, this guide makes sense of these overly traditional terms:
What’s an Oxford?
Menswear purists who caught the first Kingsman movie noted Colin Firth’s “Oxfords, not brogues” line. Since then, think-pieces and fashion guides have attempted to make sense of it.
We're not going to go into that level of detail, or think this moment is worthy of debate. Instead, it all boils down to a traditionalist sentiment: Men’s dress shoes should be smooth and pure looking. Brogue details mar that.
So, to start, what is an oxford? Deceptively similar to the derby, which we’ll address further down, an oxford shoe has a closed lacing system. The eyelets are added under the vamp – not on top, as is the case with many shoes – and the laces “close” the front.
For reference, look at the area between the tongue and foot box: With derbies, you’ll notice an upside down “V,” and with oxfords, it’s a clean line. This precision makes it a given for black tie dressing.
As a note, British oxfords tend to have five pairs of eyelets, while American oxfords usually have six. As you break in your pair, regardless of origin, you might notice that “V” space, but with time and wear, the break closes and is no longer visible.
Origin wise, this shoe doesn’t have a clear place. Many attribute it to the Oxonian, worn by students at Oxford University in the nineteenth century. Others take it back to Scottish and Irish styles, while the cap toe Balmoral – from Balmoral Castle – is considered another possible source.
Within this template, the oxford is open to plenty of possibilities. You may encounter:
- Plain toe oxfords, featuring a smooth, rounded front.
- Cap toe oxfords, distinguished by a cap-like detail around the toe, which may appear a bit more angular.
- Brogue and wingtip oxfords, which stand out with different levels of detailing around the front and sides.
- Saddle oxfords, which feature an extra strip of leather resembling a saddle across the top of the shoe.
- Whole-cut oxfords, which appear similar to plain toe oxfords but are constructed from a single piece of leather. Certain designs, taking this concept to extremes, may even be totally seamless.
How Does a Derby Differ?
At a glance, a derby shoe doesn’t look all that different from an oxford. The demarcation, frankly, seems a bit nitpicky. Yet, if you’re abiding by formal dressing rules – and, let’s be honest, we all have to follow them at some point – derbies have always run a bit on the casual end.
This, as an asset, makes them a far more versatile shoe. In fact, in today’s smart-casual environment, a man could easily get away with a couple of derbies in his closet. An oxford, by contrast, starts to feel as limited as a solid black suit.
Still, to grow, you’ve got to understand the classics. So, in terms of decades-strong menswear rules, oxford shoes, without any style details, rank the highest on the formalwear pyramid. You can pair them with a tux or another black-tie appropriate suit, and you’ll always fit the dress code.
For the next level down – think client presentations, weddings, and networking events – the derby fills its duty. It’s dressy enough, without coming off as stuffy. These days, they’re a natural match for your chinos.
Unlike the oxford, the derby’s story is a bit clearer. They were first worn in the mid-19th century as a hunting and sporting boot. Early on in the 20th century, it transitioned into an urban gentleman style, as the open lacing offered a more comfortable, adaptable fit.
Getting Around Brogue Details
Although many men (and fashion blogs) casually refer to “brogues” as a style of shoe, they’re not a footwear category in the formal sense. Rather, all types of dress shoes – oxfords, derbies, and plenty of boots – can feature brogue details.
The perforations or holes, which vary in size, differentiate a brogue from a smooth, plain-toe pair, and for this reason, the addition’s seeming ostentatiousness pushes the usually formal-leaning oxford out of the black-tie dress category.
That’s not to say an oxford brogue isn’t a dress shoe. Instead, shifting style rules have turned it into a more adventurous formal item – the broguing, in this case, adds statement appeal, and shows a man’s not afraid to put himself out there, to a certain extent.
Outside of these strictly formal occasions, brogues have the same effect: They’re far from plain, but they’re not like you’re showing up in gold-colored snakeskin loafers. Rather, they’re a happy (and often workplace-appropriate) medium for flexing your style muscles. Generally, a “brogue” is built upon a derby silhouette.
Like the derby, the brogue has more rugged origins: Specifically, a workman’s shoe dating back to the 16th century in Scotland and Ireland. Initially, the perforations were functional: They allowed moisture to pass through as the wearer walked through wetlands.
They turned into a gentleman’s staple when the Duke of Windsor started wearing them casually in the 20th century. These styles tended to have a sleeker look and floral-patterned stitching.
Design wise, brogues fall into a couple of types:
- Semi-Brogue: Sometimes called a half- or quarter-brogue depending upon the detail level, these shoes sit along the line of formal and casual, and don’t go far into statement territory. You can easily wear them to work, weddings, and any occasion that doesn’t call for black-tie dressing.
- Wingtip Brogue Although the degree of detail varies, one feature distinguishes a wingtip from other types of brogues: the “M” or “W” design on top of a cap toe. At one point, they were a more flashy, upscale style. These days, wingtips have migrated into a more sophisticated casual shoe – essentially, smart-casual footwear with some panache.
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