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From Monks To Moccasins – 7 Shoe Styles To Know

No matter how good your outfit is, if you don’t finish it off with the right shoe, you might as well go out naked. And the first step to nailing that is understanding the different types of shoe options at your disposal. But for how much footwear-choice can make or break a look, people’s knowledge of shoes doesn’t really extend beyond “yeah that’s a dress shoe”. Is it a dress shoe though? I guess.

The same way your straight cut unsanforized 13 oz. raw selvedge denim are jeans or your Shinki suede cossack jacket is a leather jacket, right? The point is, you know the stitch count of the shirt you’re wearing, it’s about time you could seamlessly differentiate between the core 7 shoe styles to know.



Viberg Natural Chromexcel Derby, available for $682 from Lost & Found

First on the list is the Derby, a versatile semi-dress option that can work with denim and chinos up to more formal wear if necessary. The derby gained a following by the sporting and hunting crowd of the 1850s before being approved for town-wear by the 1900s. In the world of dress shoes, the derby’s defining combination is its open lacing system and quarter construction. Basically, this means the leather tabs where the eyelets are aren’t sewn down to the tongue but free to lift up at the bottom as well as the top, and the shoe is made from several larger pieces of leather.



Alden Plain Toe Blucher, available for $542 from Lost & Found

Similar to the derby, the blucher features an open lace construction but instead of quarters, its upper is one piece of leather resulting in a smoother look. Often labeled interchangeably with the derby, it too is semi-formal but with a look more suitable for dressing up than down.

For reference, my OIM professor in college wore what I now know are bluchers. The name of the blucher is credited to Gebhard Leberecht von Blücher, the 18th-century field marshal, who commissioned improved leather footwear for his soldiers. Confusingly, many makers will use the terms blucher and derby interchangeably as there is a contrasting belief that blucher is simply the german term for the aforementioned derby.



Shoe The Bear Nate Leather Oxford, available for $175 from Stag Provisions

If we are ramping up the fancy scale, at the top of the list is the oxford. No, not thee Oxford but also yes, kind of thee Oxford, of shoes that is. Although similar to the derby and blucher, the biggest distinction is its closed lacing system making it a more form-fitting, sleek option.

Its name is derived from the Oxonian, a half-boot with side slits that gained popularity at Oxford University in 1800. Definitely not for the faint of outfit, the more you dress up, the better they’ll complement your look.





Grant Stone Traveler Penny Loafer, available for $279 from Heddels Shop

Characterized by their lack of laces, loafers and slippers are highly versatile shoes that can elevate the laziest outfits, making them seem completely intentional. They can also polish off a suit and tie without going overboard.

Probably the most popular iteration of the loafer is the penny loafer which was inspired by the Norwegian Moccasin and popularized by prep school students of the 1950s before becoming full-fledged American in the 60s. They feature a strip of leather across the saddle with a diamond cut-out where it’s rumored that the younger crowd used to stuff pennies. It was their video games.



Yuketen Semi Handsewn Maine Guide available for $795 from Clutch Cafe

Traditionally, moccasins consist of a sole and sides made from one piece of leather that has been stitched together at the top and sometimes featuring a vamp. Its origins are with indigenous people of North America and depending on terrain either featured soft or hard soles.

Today, outdoor moccasins maintain their leather upper and stitched construction but feature studier soles made from rubber. They can also feature laces around the edge of the upper which are usually just an ornamental detail, but on some models can actually help tighten the mocassin if need be. Predominantly used for more casual adventures, the moccasin shines all year round.



Carmina Double Monk Straps 80544 available for $416 from Lost & Found

The monk is a slip-on dress shoe that features a multi belt strap style closure. Its name was inspired by the strapped sandals worn by monks centuries ago. An acquired taste, the Monk Strap is a striking look when pulled off correctly.

Deck/Boat Shoe


Paraboot Barth Deck Shoe, available for $225 from Dick’s

Originally created to provide grip for boating and sailing, this casual shoe has skyrocketed in popularity, likely because of its ability to balance style with ease. In many ways similar to the moccasin, the boat shoe is slightly more preppy or fratty — and as previously mentioned — the sole is more specialized.

Passable with just about anything besides a suit or athletic wear, the boat shoe rules the land and sea.

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