Floppy Shoes
I love floppy shoes, particularly for wearing on warm weather days. By floppy, I mean what’s usually referred to as unlined - a term that’s kind of a misnomer since few shoes are truly made without any lining. Like with neckties, when a company describes their shoes as unlined, what they usually mean is that they’re partially or lightly lined, as some lining is often still used to give the shoes some structure. 
To explain, a well-made pair of leather shoes will usually have a full leather sock liner built in. That means two pieces of leather are joined together to form the upper. There’s the leather that faces the outside world, and the leather that touches your feet. By joining these two pieces together, you get something that has a bit more structure and will holds its shape better. Without the lining, however, you get a softer, more comfortable shoe. Whereas most leather shoes need a break-in period, unlined shoes will feel like slippers on first wear. 
My own floppy unlined shoes are by Alden. I have two pairs of their suede chukkas – one in snuff suede and the other in tan. The bottom is built on Alden’s flex welt sole, which is a thin, water-locked, oiled leather. It’s exceptionally flexible and complements the shoes’ unlined construction well. The combination of the two makes for a lightweight, comfortable boot that looks as great with jeans and chinos as they do with grey wool trousers.
They’re expensive at full retail, but sometimes you can find them for about half off on eBay. Allen Edmonds has a similar model called the Amok. The shape is slightly sleeker, and it comes in at $250. Nordstorm describes it as having a leather lining, but you can see this isn’t true when you zoom in on the photos.
Alden also makes unlined derbys and loafers, which you can find through Harrison, Unionmade, Leffot, and Shoemart. The unlined loafers also come in shell cordovan (most notably in the well-beloved Horween #8, which has a beautiful reddish-brown color). That one is sold exclusively through Brooks Brothers, who has them on discount today as part of their Corporate Card event (30% off for anyone who holds a Brooks corporate card). For something a bit more affordable – but no less well made – consider Rancourt. They have a made-to-order system that can allow you to order any of their shoes unlined. I’m personally thinking of getting some snuff suede unlined penny loafers from them in the next month or so. 
(Photo credit: Unionmade)

Floppy Shoes

I love floppy shoes, particularly for wearing on warm weather days. By floppy, I mean what’s usually referred to as unlined - a term that’s kind of a misnomer since few shoes are truly made without any lining. Like with neckties, when a company describes their shoes as unlined, what they usually mean is that they’re partially or lightly lined, as some lining is often still used to give the shoes some structure. 

To explain, a well-made pair of leather shoes will usually have a full leather sock liner built in. That means two pieces of leather are joined together to form the upper. There’s the leather that faces the outside world, and the leather that touches your feet. By joining these two pieces together, you get something that has a bit more structure and will holds its shape better. Without the lining, however, you get a softer, more comfortable shoe. Whereas most leather shoes need a break-in period, unlined shoes will feel like slippers on first wear. 

My own floppy unlined shoes are by Alden. I have two pairs of their suede chukkas – one in snuff suede and the other in tan. The bottom is built on Alden’s flex welt sole, which is a thin, water-locked, oiled leather. It’s exceptionally flexible and complements the shoes’ unlined construction well. The combination of the two makes for a lightweight, comfortable boot that looks as great with jeans and chinos as they do with grey wool trousers.

They’re expensive at full retail, but sometimes you can find them for about half off on eBay. Allen Edmonds has a similar model called the Amok. The shape is slightly sleeker, and it comes in at $250. Nordstorm describes it as having a leather lining, but you can see this isn’t true when you zoom in on the photos.

Alden also makes unlined derbys and loafers, which you can find through Harrison, Unionmade, Leffot, and Shoemart. The unlined loafers also come in shell cordovan (most notably in the well-beloved Horween #8, which has a beautiful reddish-brown color). That one is sold exclusively through Brooks Brothers, who has them on discount today as part of their Corporate Card event (30% off for anyone who holds a Brooks corporate card). For something a bit more affordable – but no less well made – consider Rancourt. They have a made-to-order system that can allow you to order any of their shoes unlined. I’m personally thinking of getting some snuff suede unlined penny loafers from them in the next month or so. 

(Photo credit: Unionmade)

Camp Mocs

In the last 100 years or so, Americans have invented some of the most classic slip-on shoe styles for men, but they usually start with an idea borrowed from somewhere else. G.H. Bass, for example, invented the classic American penny loafer, but they came up with the idea after having seen moccasin style shoes made and worn by farmers in Norway. Alden, similarly, came up with the tassel loafer when actor Paul Lukas asked if they could make something similar to a pair of tasseled oxfords he picked up in Europe.

Yet another example is the camp moc, which was invented by LL Bean’s founder, Leon Leonwood Bean, in 1936. He came up with a slip on shoe that could be worn out in the wilderness by taking some ideas from Native American moccasins. Like many of his company’s clothes in the mid-century, LL Bean’s camp mocs eventually made their way to college campuses. At that time, many students liked to repurpose outdoor clothes such as parkas, trail mocs, and camp mocs for everyday use. 

LL Bean still makes their camp moc, but I’m afraid it’s not what it used to be. It’s a decent shoe, to be sure, and probably the most affordable one out there at $79. However, the leather quality leaves a lot to be desired.

If you can afford them, you can find better camp mocs from Oak Street Bootmakers, Rancourt, and Quoddy. Rancourt’s has the advantage in being fully made-to-order, so you can customize them however you’d like. Alden also makes a model through their Cape Cod Collection. It’s typically built on a less than ideal driving sole, but Harrison seems to have it available on a leather sole with a stacked heel (less traditional, but nice looking). I also like the ones from Russell Moccasin (Sid Mashburn has better photos) and Eastland’s Made in Maine. Eastland’s Made in Maine collection is significantly better than their mainline (which also has a camp moc), but to be honest, I find them a bit overpriced for their quality. On the upside, they’ve somehow escaped internet hype, so it’s easier to find them on sale and (occasionally) eBay at heavily discounted prices. Their camp moc is a pretty good value if you can find them half off or so, but note that they’re a bit low on the instep.

Two other good makers are Arrow Moccasins and Town View Leather. They’re both small, family-owned operations that make fully handsewn moccasin style shoes. I like them a lot, especially at their modest price point. They give you the option of making your moccasins with a crepe or double leather sole. I have a pair of double leather sole moccasins from Arrow, and like them for short walks and use around the house. Jesse has also taken his for longer walks. The leathers these guys use is thick and supple, and nicely conform to your feet after a few months worth of use. 

At their core, however, camp mocs are meant to be abused and worn down to the ground. Many of the aforementioned brands make camp mocs from higher-quality leathers, which means they’ll last a bit longer and look better with age. However, even the LL Bean ones have a certain charm as they’re falling apart. Buy ones that are right for your budget and feel free to put some hard use into them.

(Photos via Reddit)