Deep Dive

Sid's All-Time Favorite Dress Shoes

Shoes have always been a big deal for me. They're literally a foundational piece... they ground you and set you up for the day. And just like a tree, it's hard to look strong and bear fruit if your roots aren't right. In recent years, we've seen this continued casualization when it comes to dressing for work. But we like to look polished, and a great pair of shined-up dress shoes can get you there. Pretty much everything we do is a combination of Italian-English-American. And we're constantly going back and forth to get the best qualities out of all three of those. The Italian piece is a style thing... the Italians (and the Internet) call it 'sprezzatura', but it's really just a bit of your own personality. The English component is all about the construction — the Goodyear welting and the benchmade tradition — and then the American part comes in when you wear it with some ease, when you're comfortable in your own skin. Not too much flash, but not too wallflower, either. It should feel natural. And while I love every shoe we make, these are the five that strike that perfect balance.



The cap-toe is a super-classic shoe, and we make ours on a special, deep-from-the-archives last in England. The last is like the heart of your shoe — it's that foot-shaped wooden mold that gives the shoe its shape during construction. The last establishes the overall silhouette, the width, the arch, the swing where the throat comes around to the toe... it's a super-important piece. So our cap-toe has presence, but not too much, and the toe is great because it's not too flat or too round or too pointed. If you're starting out, your first pair should probably be the espresso color, which is a darker brown with a little allover burnishing on it, not just on the toe. It goes with every color except for black. Charcoal, mid-grey, pearl grey, navy, any shade of blue, olive... the brown is always good. You can wear it with any suit, with dress trousers and a sport coat, or take it down a notch with jeans and a collared shirt — though you probably wouldn't wear it with a polo — but with jeans and a sport coat, it can be pretty fantastic. The versatility is incredible... there's no season you can't wear it.

THE VIBE: classic elegance

THE SHOE FOR:the guy who wears a suit to work every day

THE NO-BRAINER LOOK:navy high-twist suit + striped shirt + foulard tie + alligator belt + navy socks

JUST DON'T:go sockless with these... it doesn't look quite right.

Double monks are a heck of a lot more versatile than you may think... and, no, they haven't been overplayed. This was the first shoe I worked on when we opened up shop back in 2007. Our riff on this very old-school English style, with that super-done-up Savile Row feel to it, and at the time, I only knew of one other company that was making these, and it was John Lobb. I had a pair of those years and years ago, and at first I thought "man, that is a lot of shoe. That is too much shoe. How can I even wear that?" But sure enough, you take the plunge and you realize, hey, maybe this shoe goes with everything. In a strange way, it's even more versatile than the cap-toe... it goes with suits, jeans, khakis, grey trousers... okay, not shorts, but everything else. And like I said, we opened the store with these in autumn brown calfskin, and a lot of guys had that same reaction. Just... "oh, that shoe is not for me." But once you got someone in a pair, anyone from a 17-year-old kid to an 85-year-old grandfather, he'd be off to the races. The heft of the buckles gives it almost a military feel. The best color, to me, is the espresso. You might say, "wait a minute, I just got the cap-toes in espresso." That's fine! It's a completely different shoe. The cap-toe is better for events that require a little more discretion, a little more subtlety. Like a boardroom meeting, you might not want to show up in these. It's a fantastic pair of shoes, though.

THE VIBE: cool, but not trying too hard

THE SHOE FOR: the guy who wears a tie because he wants to, not because he has to

THE NO-BRAINER LOOK:navy high-twist jacket + graph-check shirt + knit tie + grey trousers + bridle belt

JUST DON'T: wear these to something super-formal... you need something a little quieter for the boardroom


tassel loafers on the floor

I always love a tassel loafer. Alden really originated this style, as a way of amping up the classic penny loafer, giving it a little extra something. Our take on it has that equilibrium that we love, again, where it's a very English expression of an Italian loafer, so you get that personality, but also the construction and attention to detail: Goodyear welting, full-grain calfskin, nice burnish, made mostly by hand in Italy. But since it slips on and off so easily, it can take on the casual knockaround vibe of a classic American shoe. (That's also why we say that if you're traveling, it might be the best shoe to take.) I like that versatility. It can run the gamut. It's very elegant with a suit... and this pair, you actually could wear with a pair of shorts. I wouldn't, but you could. For me, I dig the dark brown calfskin, but if you like a little more color, or if you want to take things to a slightly more casual place, the autumn brown is the one. It's really the better sport coat shoe. And it parties well with other colors. Blue jeans are great, white jeans are great, but you can take it to another level with bright trousers, like a green or a pink. You throw on a polo shirt and a cool belt, and you're set.

THE VIBE: old-school traditional

THE SHOE FOR: the frequent flier

THE NO-BRAINER LOOK: navy leno jacket + blue end-on-end shirt + irish poplin tie + colorful sport trousers

JUST DON'T: impossible to imagine where and when you can't wear these... I practically sleep in mine

The Chelsea... whadda ya gotta know? It's great. It's an unusual boot. It's very, very English, kind of like a jodhpur boot. Worn with pants, it gives you a very elegant line. In the cooler months, you could honestly wear a pair of these every day. It's similar to the way a lot of Texans wear cowboy boots as a kind of default... but a little more elegant and not quite as opinionated. And that side gusset makes it easy to get in and out of. Not to mention the walking-around part... if you're on the move, or getting up and down all day, you wanna be in a pair of Chelsea boots. They hold up. I'd say the brown calfskin version is pretty fantastic, and again, very versatile. You can wear it with a suit, or a pair of jeans, corduroys, moleskins, whatever. And while it's very polished, it's got a bit of a rock-n-roll vibe... it's a second-look shoe. There's some attitude to it. And actually, the black calfskin Chelsea boot is my go-to formal shoe in the winter. Super bad... it gives a tux a little more edge without getting too rebellious. No one's going to side-eye you at the black-tie wedding, but they're a touch more interesting than a pair of lace-ups.

THE VIBE: English cowboy

THE SHOE FOR: the guy with a little edge

THE NO-BRAINER LOOK: your favorite sport coat + sky roxford shirt + grey trousers or jeans + dark brown dress belt

JUST DON'T: bust these out in the summertime... they're best from September to April



penny loafers on the floor

When it comes to casual men's loafers, this is the one. Sure, it's a penny loafer, but it's a really elegant penny loafer. The profile of this pair is especially strong. There's a nice sidewall that runs from the ball of your foot all the way around to the vamp, and that gives it a more formal presence. Actually, one of the clinchers here is the half-rubber studded sole, similar to Dainite, that works hard without calling attention to itself. Because you can't see it unless you flip the shoe over. So you get some extra comfort without looking like you're wearing "comfort soles" from the side. It kinda does double-work... and in that regard, it's very, very cool. The chocolate suede is hands-down the most versatile... just make sure to hit it with a suede brush — do it lightly, don't grind on it — every couple of weeks to keep it from picking up too much dirt. And I know I'm a broken record on this, but the versatility piece is huge. So it's fantastic with a suit that's not too dressy, like a hopsack or a high-twist, but can also go with trousers, a pair of jeans, socks or no socks... again, everything except black!

THE VIBE: casual elegance

THE SHOE FOR: the weekender... and the Friday meeting he's got to get through first

THE NO-BRAINER LOOK: your favorite sport coat + non-pattern-pattern sport shirt + natural jeans + sharkskin belt

JUST DON'T: wear 'em with black


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