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)

The Navy Sport Coat of Shoes
In my opinion, there’s no style of footwear more underrated or versatile than the dark brown derby. Derbys are shoes that have their eyelet tabs left on top of the vamp, which differs from oxfords, where the eyelet tabs are sewn underneath. This “open lacing” design makes derbys more casual than oxfords, and in dark brown, they’re formal enough for everything except the most formal occasions, and casual enough for everything but the most casual environments. For this reason, I would consider them the navy sport coat of shoes.
Unfortunately, their versatility and value isn’t often recognized. Men will often buy four or five oxfords before they even consider a derby. I assume this is because they get their shopping directions from magazines and photo-driven Tumblr sites, where men are often shown wearing oxfords and suits with some kind of vague sex appeal
“Give me ten of those!,” they’ll say. “In every shape and color!”
The problem is that these men fail to remember they rarely wear suits, and such a dressy shoe can look incongruent with what they typically have on. Jeans with waxed cotton jackets, khakis with just a button-up shirt, odd trousers with sport coats – with all these ensembles, a dark brown derby will almost always be a better choice than the more formal oxford. 
To be sure, this isn’t to say that oxfords should only be worn with suits and derbys with everything else. Many things determine the dressy-ness of shoes. Black is more formal than brown; calf is more formal than suede or shell; smooth leather is more formal than grained; plain is more formal than brogued; single soles are more formal than double (or Dainite); and yes, oxfords more formal than derbys. Add to these the consideration that certain casual styles (such as monkstraps) can be worn with suits, and certain suits should only be worn with casual shoes (such as linen suits), and things can get quite complicated indeed. 
But that’s an aside. The point here is that for almost everything you’re likely to wear, a dark brown derby is probably a better choice than the sleeker, more formal oxford. Above are three of mine, shown in increasing order of formality – Ralph Lauren shell cordovan shortwings; Edward Green Norwegian split toes in dark oak calf, and Meermin cap toes in dark brown Annonay Naturcalf. You don’t need three, but at least get one. 

The Navy Sport Coat of Shoes

In my opinion, there’s no style of footwear more underrated or versatile than the dark brown derby. Derbys are shoes that have their eyelet tabs left on top of the vamp, which differs from oxfords, where the eyelet tabs are sewn underneath. This “open lacing” design makes derbys more casual than oxfords, and in dark brown, they’re formal enough for everything except the most formal occasions, and casual enough for everything but the most casual environments. For this reason, I would consider them the navy sport coat of shoes.

Unfortunately, their versatility and value isn’t often recognized. Men will often buy four or five oxfords before they even consider a derby. I assume this is because they get their shopping directions from magazines and photo-driven Tumblr sites, where men are often shown wearing oxfords and suits with some kind of vague sex appeal

“Give me ten of those!,” they’ll say. “In every shape and color!”

The problem is that these men fail to remember they rarely wear suits, and such a dressy shoe can look incongruent with what they typically have on. Jeans with waxed cotton jackets, khakis with just a button-up shirt, odd trousers with sport coats – with all these ensembles, a dark brown derby will almost always be a better choice than the more formal oxford.

To be sure, this isn’t to say that oxfords should only be worn with suits and derbys with everything else. Many things determine the dressy-ness of shoes. Black is more formal than brown; calf is more formal than suede or shell; smooth leather is more formal than grained; plain is more formal than brogued; single soles are more formal than double (or Dainite); and yes, oxfords more formal than derbys. Add to these the consideration that certain casual styles (such as monkstraps) can be worn with suits, and certain suits should only be worn with casual shoes (such as linen suits), and things can get quite complicated indeed.

But that’s an aside. The point here is that for almost everything you’re likely to wear, a dark brown derby is probably a better choice than the sleeker, more formal oxford. Above are three of mine, shown in increasing order of formality – Ralph Lauren shell cordovan shortwings; Edward Green Norwegian split toes in dark oak calf, and Meermin cap toes in dark brown Annonay Naturcalf. You don’t need three, but at least get one.