KahnJunction: Sunday Shoes

A Shoe Guide for the Well Dressed Young Man

There comes a time in every young man’s life when he must don formal shoewear for the first time. Sure, he has worn formal shoes before, but only after they had been thrown his direction after mom has gotten him something nice to wear for his random cousin’s wedding. 

At this point in his life, he’s more than likely still comfortably sitting in fashion purgatory. However, his sense of style is beginning to mean something to him. He realizes that his shoes are an integral part of his style, especially at formal events. 

For that young man, (even if it’s you, the reader) I have written a guide that should help him begin this journey.

Oxfords,  Derbys, and  Brogues

Oxford, Derby, and Brogues as seen on Amazon.com

The bread and butter of your formal shoewear, these three shoes are approachable, laced, and formal. 

The primary distinction between the three of these are the laces: Oxford laces are “closed,” meaning that the gap between either side of the laces is quite short. Derby laces are “opened,” meaning there is a more significant gap between either side of the laces. Brogues on the other hand are not defined by their lacing, however. The calling card for the brogue lies in its stylized perforations, usually featured on the toe cap and around the seams of the fabric (though they sometimes appear elsewhere). 

Keep in mind that a brogue shoe can still be  an Oxford or a Derby, it simply depends on the positioning of the laces.   


Loafers as seen on Amazon.com

It’s Saturday and your friend, Niles, invites you for an afternoon polo match. You arrive in your BMW (or other German vehicle that you think is the epitome of your social class). You barely win the match and return to your car to see  Niles revs his engine as he backs out of his parking spot, and zips onto the street (no turn signal, as is customary). For a brief moment you think about racing Niles, but you remember Father saying he wouldn’t bail you out again–you are on probation after all. You hang your head. 

Despondent, you look down at your feet, resting on the pedals. What kind of shoes are you wearing? Probably loafers. 

Loafers straddle the line between smart casual and semi-formal wear with grace; Loafers occupy the classier niche within the broader category of slip-on shoes. In fact, they are one of the few items on this list that makes socks completely optional, though I would at least recommend some  no-shows. While loafers may feature a buckle or some form of laces (docksiders), these are often purely cosmetic, and many will forgo them in favor of a lighter, simpler, shoe. Loafers may also feature tassels or an interesting leather fringe along the topside of the shoe. These are often referred to simply as “tassels” and “kilties,” respectively. 

Chukkas & Desert Boots

Chukka/Desert boots as seen on Amazon.com

Chukkas represent a man’s first tentative step into the transitional world between shoes and boots. 

After all, what is a chukka? Some people will tell you it is a boot, some people will tell you it is a shoe. I’m here to tell you that it really doesn’t matter–it has qualities of both. Unlike the lower cuts on the previous two items on the list, the chukka boot/shoe raises the quarter and topline to around the center of the medial malleolus. Traditionally, chukkas are made from suede, though leather chukkas are becoming more popular. Leather chukkas with a raised, rubber sole are simply referred to as desert boots. Desert boots also typically raise the topline and quarter to the midline or top of your ankle. Chukkas, like Chelsea boots and desert boots, are a mainstay in men’s rugged casual fashion. 

If you choose to get yourself a pair of suede chukkas, as with any nice shoe, make sure you research and figure out how to take care of the material–in this case suede. Not doing so could result in an expensive mistake. It is often better not to learn the hard way. 

Chelsea Boots

Chelsea boots as seen on Amazon.com

I’m just gonna say it–I think Chelsea boots are weird–and I love them. This boot rocks its way to the top of our list in terms of how high its cut is, as the topline usually ends right around the top of your ankle. The iconic feature of this boot is the elastic fiber gussets that run along either side of the quarter. This gusset allows for the boot to stretch in order for the wearer to get it on, but then allows the boot to return to its original shape. This simple design allows the boot to completely abandon the conventional need for laces and buckles. Chelsea boots nestle themselves nicely into the rugged casual niche, but their versatility can also find them as part of a streetwear or grunge ensemble; a more affordable substitute to a pair of Doc Martens.

These are the basic shoes with some basic rules. But remember, there are myriad styles within each category, and rules are made to be broken. Even though Oxfords are typically accompanied by dress socks and slacks, if you’re feeling a little experimental, why not pair them with shorts and some no-shows? If you’re tired of how your dark wash jeans look with your desert boots, why not pinroll the bottom hem for some lighter color? You should begin to view your shoes as another opportunity to accessorize and express yourself and not an obstacle that you have to get around. 

The most important thing is that, no matter what you decide to wear, you are confident in your look. Though this may not come easily at first, if you’re confident in your stylistic decisions, you’ll look sharp regardless of what you’re wearing on your feet.

Benjamin Kahn is a staff writer for the UB Post. He writes a weekly column, KahnJunction.

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