Chelsea Boots
For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).
Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).
Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.
For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).
If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Chelsea Boots

For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).

Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).

Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.

For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).

If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Q and Answer: Ten In-Between Shoes

Matt asks: I need a new pair of shoes!  What I have right now is either too casual (a sneaker) or too formal (a fancy dress shoe), but I’m trying to figure out something in between. Any suggestions?

This is a question we get a lot. For men who want to wear something a little more put-together than their beat-up Nikes, but aren’t yet ready for a full-on sportcoat-trousers-dress-shoes ensemble, is there anything in between?

The simple answer is: yes. Here are ten choices for casual footwear that will keep you a head above the dirty sneaker crowd. (It’s a little tougher in the summer, so I’ll start there - the pictures run left to right and top to bottom.)

  1. Refined sneakers. When choosing sneakers, look for simplicity. White’s a great color for spring and summer, black and brown will do you well in the cooler months. You want as few details as possible here, and if you’re going to try and dress them up, they should be clean and sharp. I’ve got some Common Projects, the gold standard for this kind of thing, pictured above, but if you can find similarly simple leather sneakers from a brand that doesn’t cost a bajillion dollars, go for it.
  2. Boat shoes. While their ubiquity the past few years or their inherent preppiness might be a turn-off, boat shoes remain the default casual summer shoe (non-sneaker category). Wear them without socks in pretty much any casual situation during the hot-weather months. Then put them away.
  3. Espadrilles. These are the classic European vacation shoe - what Cary Grant might wear to the French Riviera. They’re cheap, comfortable and refined. Just don’t try to wear them outside of summer vacation, and for goodness’ sake don’t wear those awful Toms.
  4. Crepe-soled Chukkas. Desert boots are a comfortable, good-looking mostly-casual shoe for nine months of the year. Like boat shoes, they’re starting to overwhelm with their ubiquity, but if you try an alternative style like the calf version above, you can get a little more refinement and a little less “been there, done that.” (I can’t believe I just typed “been there, done that.”)
  5. Leather-soled Chukkas. Chukkas with leather or dainite soles like the brown suede pair above are one of the most versatile shoes you can own. They’re great with jeans, and in a pinch they could even be worn with a suit (though maybe not in suede). 
  6. Camp Mocs. Camp mocs are the cool-weather equivalent of the boat shoe. Inexpensive, casual, preppy and a little more refined than sneakers. The LL Bean Blucher Moc is the standard here, though the quality isn’t as high on them as it once was. Works great with jeans or chinos, but not so much with a more formal look.
  7. Plain-Toe Bluchers. This is the classic casual shoe. My own pair is an old double-soled pair of Florsheims in shell cordovan. I wear them with everything short of a suit. Black looks like security guard shoes, so avoid it. Brown is a touch more casual than burgundy, and crepe soles a touch more casual than leather.
  8. Country Brogues. Grenson is the classic maker of real country brogues, so that’s what you see above. The leather in shoes was originally perforated by folks who lived in marshy, wet conditions and wanted shoes that shed water. It’s purely decorative now, but still casual relative to other oxfords. If you want to wear brogues casually, look for prominent broguing, a stout shape and heavy soles. These are too casual for most suits (save country suits like corduroy or tweed), but if they’re clunky enough, they can stand up to blue jeans well. The boot equivalent of these shoes is even more casual. Note, also, that crepe soles or (especially) suede can turn down the formality of most dress shoes.
  9. Work and Outdoor Boots. There are a broad range of work-style boots. I’ve pictured something in the middle, the Red Wing Gentleman Traveler. On the casual end are hunting and hiking boots (like Danners) and real work boots (like traditional Red Wings, with lug soles and moc toes). I love my Alden Indy Boots, which are moc-toed, but otherwise quite refined - I wear them with chinos or jeans and a casual blazer all the time. Also in this category are military-inspired boots, like Polo Rangers.
  10. The Chelsea Boot. I’ve pictured a pair by the Australian maker R.M. Williams. A hefty, chunky Chelsea like these is more casual. A more refined model can even be worn with a suit. In fact, the Chelsea is probably the shoe that most comfortably goes from casual to formal.

Remember: city is more formal than country. Leather soles more formal than rubber (and lug soles the least formal of all). Smooth leather is more formal than textured, which is more formal than suede, which in turn is more formal than unpolished. Shoes are more formal than boots. Shapely is more formal than clunky.

And always, always stay away from hybrids. Nothing good can come of two shoes mating.

Finding a level of formality that’s between slovenliness and traditional business dress is vital for anyone who isn’t a slob or a traditional businessman. Hopefully this will set you on your way.

Folks are always asking me about more affordable boot options for the cool-weather months. It makes sense - most of the good stuff starts in the $300-400 range and goes up from there. That’s a serious dent in anyone’s pocketbook. It’s tough to find something that’s both cheap and recommendable.
These look like they might be an exception: the Lands’ End Fulton. A Chelsea boot can be very versatile - it can be casual enough for jeans, and can even be pulled off with a suit in some circumstances. It also moves easily from day to night. They’re a classic utility player. These ones look like a bargain, too.
It can be tough to find shoes (to say nothing of boots) made of actual full-grain leather for less than $300, and these guys retail for $158. Add one of those 25 or 30% off coupons that Lands’ End is always passing around, and you’re barely over a hundey.
These aren’t RM Williams or Crockett & Jones. They’re “imported” (presumably made in China), they advertise a “full leather welt,” but don’t say whether the welt is functional or decorative, and I’m sure that full-grain leather falls short of ultra-premium. Still, this looks like a workhorse boot for an excellent price. The best part is that they’re Lands’ End, so if they don’t work out for any reason at all, you can return them, no questions asked.

Folks are always asking me about more affordable boot options for the cool-weather months. It makes sense - most of the good stuff starts in the $300-400 range and goes up from there. That’s a serious dent in anyone’s pocketbook. It’s tough to find something that’s both cheap and recommendable.

These look like they might be an exception: the Lands’ End Fulton. A Chelsea boot can be very versatile - it can be casual enough for jeans, and can even be pulled off with a suit in some circumstances. It also moves easily from day to night. They’re a classic utility player. These ones look like a bargain, too.

It can be tough to find shoes (to say nothing of boots) made of actual full-grain leather for less than $300, and these guys retail for $158. Add one of those 25 or 30% off coupons that Lands’ End is always passing around, and you’re barely over a hundey.

These aren’t RM Williams or Crockett & Jones. They’re “imported” (presumably made in China), they advertise a “full leather welt,” but don’t say whether the welt is functional or decorative, and I’m sure that full-grain leather falls short of ultra-premium. Still, this looks like a workhorse boot for an excellent price. The best part is that they’re Lands’ End, so if they don’t work out for any reason at all, you can return them, no questions asked.

It’s On Sale
Peal & Co. Chelsea Boots
The Chelsea boot can go from a casual suit all the way to dark jeans. Black Chelseas, in particular, are a great “going out” shoe for evening wear. Sharp, but not business-y.
$224 from $528 at Brooks Brothers (Use code SPG111X)

It’s On Sale

Peal & Co. Chelsea Boots

The Chelsea boot can go from a casual suit all the way to dark jeans. Black Chelseas, in particular, are a great “going out” shoe for evening wear. Sharp, but not business-y.

$224 from $528 at Brooks Brothers (Use code SPG111X)

Q and Answer
Eric writes:
My problem seems almost too basic. I am having a problem finding a good pair of shoes for my new black jeans & pants. I generally wear casual clothing and generally in fall shades. I don’t have the money to buy shoes in every color that might match shirts I wear. The navy blue topsiders and brown Clarks that I own look awful with black pants. The most common shoe that I see with black jeans is black Adidas (Sambas, I think) and black Chuck Taylors. I find Chuck Taylors way too uncomfortable and I would do Sambas, but I am hoping you might know of a shoe that is casual, but not sneakers like my other shoes that goes well with black jeans. All the shoes I am finding that I like are a more natural fit for blue jeans or are white and might quickly get too dirty.
Something you learn quickly about black clothes is how difficult they are to match to anything.  You buy them thinking they’re neutral, but they’re not.  You can wear grays and whites and vary texture, but all of a sudden, you realize you have a black, grey and white outfit, and you’re desperately looking for a red scarf or something so you don’t look like an undertaker.
That said, black is the traditional color of going out at night, and of artsiness, so it isn’t without value.  One shoe you can pair both with black jeans and trousers is a Chelsea boot.  It’s not the kind of thing you would wear in a business context, but it could certainly be paired in the evening with your good jeans or with a pair of black or gray trousers.

Q and Answer

Eric writes:

My problem seems almost too basic. I am having a problem finding a good pair of shoes for my new black jeans & pants. I generally wear casual clothing and generally in fall shades. I don’t have the money to buy shoes in every color that might match shirts I wear. The navy blue topsiders and brown Clarks that I own look awful with black pants. The most common shoe that I see with black jeans is black Adidas (Sambas, I think) and black Chuck Taylors. I find Chuck Taylors way too uncomfortable and I would do Sambas, but I am hoping you might know of a shoe that is casual, but not sneakers like my other shoes that goes well with black jeans. All the shoes I am finding that I like are a more natural fit for blue jeans or are white and might quickly get too dirty.

Something you learn quickly about black clothes is how difficult they are to match to anything.  You buy them thinking they’re neutral, but they’re not.  You can wear grays and whites and vary texture, but all of a sudden, you realize you have a black, grey and white outfit, and you’re desperately looking for a red scarf or something so you don’t look like an undertaker.

That said, black is the traditional color of going out at night, and of artsiness, so it isn’t without value.  One shoe you can pair both with black jeans and trousers is a Chelsea boot.  It’s not the kind of thing you would wear in a business context, but it could certainly be paired in the evening with your good jeans or with a pair of black or gray trousers.