in: Outfit Guide, Podcast, Style

• Last updated: September 28, 2021

Podcast #174: The Thinking Man’s Guide to Style

Since I started the site in 2008, I’ve read a lot of books about men’s style. And one of the most engaging, useful, and witty books on the topic I’ve come across is called Men’s Style: A Thinking Man’s Guide to Dress. It’s by a columnist and novelist named Russell Smith. Today on the show Russell and I discuss the philosophy of men’s style, the history of men’s clothing, why — contrary to popular belief — the great men of history were concerned about how they look, and why we should care today. We also get into practical tips on suits, shirts, shoes, etc.

Show Highlights

  • How Russell transitioned from being part of the 1980s punk scene to becoming a writer on men’s style
  • How punk rock has an underlying aesthetic and style philosophy
  • Why both conservatives and liberals are uneasy with the idea of men caring about how they dress
  • Why history’s manliest men were often flamboyant dressers
  • The military and sporting origins of the most common pieces of men’s clothing today
  • Why modern men should care about style
  • How the way you dress can be a gift to others
  • How you can look good without spending a lot of money
  • Why you need to spend the most on your shoes
  • How to start a basic wardrobe
  • The future of men’s style
  • And much more!

Book cover, style by Russell smith.

If I had to pick one book to recommend for learning the basics of men’s style, Russell’s book would be it. Not only does he manage to cram in a good amount of nuts and bolts information about clothing — what to buy, how to wear it, etc. — he makes the subject positively fun to read about. I often found myself chuckling out loud while reading it. And if you’re a fiction reader, check out Russell’s new collection of short stories called Confidence

Listen to the Podcast! (And don’t forget to leave us a review!)

Available on itunes.

Available on stitcher.

Soundcloud logo.

Pocketcasts logo.

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.


Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness podcast. Since I’ve started this site back in 2008, I’ve read a lot of books on men’s style. One of the most fun, engaging, witty books I’ve read on the topic, as well as just crammed with useful, practical information, is a book that was published a few years ago called, “Men’s Style: The Thinking Mans Guide to Dress.” It’s by a Canadian columnist and novelist by the name of Russell Smith. I’ve wanted to get him on the podcast to discuss all things men’s style.

Today on the show Russell and I discuss all aspects of style. The high level philosophical approach to men’s style. Why you should care about dressing. The history of men’s style. Why throughout history, most of human history, the most manliness of men were concerned about how they appeared and how they looked. It’s only recently where this whole aesthetic of, I don’t just care approach, and we are, why you should care, even today.

We discussed the future of men’s style, but we also get brass tacks and talk about the practice aspects of style. The type of suit you should buy if you’ve never bought a suit and you’re in the market for one. Why you should invest in a good pair of shoes. Shirts, things like that, really great information that you can take away and apply right away. Also some things for you to think about as well. Without further ado, Russell Smith and men’s style.

Russell Smith, welcome to the show.

Russell Smith: Thanks for having me.

Brett McKay: You wrote a book, it came out about three years ago called “Men’s Style: The Thinking Man’s Guide to Dress.” It’s one of the most information packed book on style, but also the most well written book. It’s just a lot of fun to read. I’m curious because you highlight this in your book, that growing up you were part of the punk rock scene. I imagine there was a lot of studded, denim jackets with sleeves ripped off, and Rancid patches sewn on and what not. Now you’re a writer so probably work from home. You don’t have to get dressed up technically.

Russell Smith: Exactly.

Brett McKay: … Could lounge around in your underwear. I’m curious. How did this interest in high men’s style and fashion get started?

Russell Smith: First of all, about punk rock. That was primarily a fashion interest. I think punk rock was primarily an aesthetic movement. It was really a movement about a new aesthetic. A movement in fashion. I don’t really think it was, particularly not in the UK, which is the movement that influenced me the most, not really a political or ideological movement. I came to punk rock through fashion really.

I’ll tell you my background. It’s interesting. My father is a university professor of English. My mother, they met at Oxford in the 1950’s, and she was a noted beauty. She always had an interest in clothes, to look good. I grew up with these two influences in my home. My house had a subscription to The Times Literary Supplement and Vogue. Those were the two biggest influences in my life.

My dad was always fascinated by the minutiae of men’s clothing. Not so much fashion as convention. Convention in men’s fashion is so much more important than it is in women’s fashion. The convention of how to do things properly and as a gentleman should, are so riven with class convention, and military traditions. Those things are actually at odds with fashion, and they keep holding men’s clothing back against fashion.

My dad, he was from South Africa, which is where I was born. He went to Oxford as a Rhodes Scholar, so was slightly outside the privileged classes at Oxford. Had a different accent, had a colonial accent, and really had to learn these conventions of proper gentleman’s behavior in a place that was highly class conscious. He learned all these conventions of the right dinner jacket, the right way to lace your shoes, to button your jacket. The right kinds of suspenders. What to call the third piece of your suit, and how to pronounce it. He taught all those things to me as a child. I grew up fascinated by these things.

Brett McKay: Interesting. I guess the punk rock thing was, you’re going to rebel against that. Was that what that was?

Russell Smith: It wasn’t … No really, it was all part of that. For me, punk rock was rebelling against blandness. Punk rock was a way of being a peacock and standing out. It was really just another manifestation of fashion. After punk rock, as a very young man I went through all the different post punk new wave manifestations of different fashions. Rockabilly, and Ska, and Goth, and New Romantic. I had long hair and make up, and scarves. Those were all just different expressions of different forms of flamboyance really. Don’t worry, I don’t dress like that anymore.

Brett McKay: It’s interesting that you make a point about how even people in the punk rock scene are very fashion conscious because there’s the general idea out there for most public. It’s, “Oh they don’t care what they look like because look at them.”

Russell Smith: Oh god. In the 1970’s, it was very much about how you looked.

Brett McKay: Right, yeah. Even when I was in high school in the 90’s, and I sort of dabbled in the Punk Ska scene. I remember just seeing these kids. How much time they would spend studying their jacket, or getting the patches right. It looked like they didn’t care, but no they really cared a lot.

Russell Smith: Oh yeah. There’s a lot of work that goes into it, yeah.

Brett McKay: Right. In the book, you make the case that style and caring about dressing well, at least for men, gets attacked or is held in suspect by both people who would call themselves conservatives socially or liberal or progressive.

Russell Smith: Right.

Brett McKay: What are the respective criticisms and how do you counter those?

Russell Smith: It’s funny. It’s pretty much the same from the left and the right. The right says that it is uncool, unmanly to pay attention to your clothing. That it’s effeminate. That’s what a social conservative would think. A leftist thinks that it is frivolous. That it is not serious, that’s it’s evidence of a wastefulness, a wasteful kind of thinking. Again, evidence of a lack of seriousness.

We have this convention in our society, and this is pretty recent. It’s only really in 20th century society, that a man should be valued only on what he does, and not on how he appears, and that any kind of preening or flamboyance appearance makes him seem less serious and less powerful. That’s really a blip in the history of men’s clothing. Men, especially powerful men, have signaled their power through finery. Right through human history. Even the most macho of warriors, military men, have the most flamboyant uniforms. Think of plumed helmets and red uniforms and all the different gold braid that goes into military uniforms. Those are really the most flamboyant outfits of all, and those are the most macho men. Think of kings and nobles showing off their status with silk and lace and finery.

It really wasn’t until the rise of democracy in the 19th century that men begin to try to appear as if they were below their social station. It was something of a liability after the French Revolution in Europe, to go around proclaiming aristocratic status. It became more fashionable to appear to be a commoner. That’s when the rise of the uniform garment begin. The matching jacket and pants of a dark fabric that became the men’s suit. That began it’s rise in Europe in the early 19th century. From about the mid-19th century on, it hasn’t changed. It’s the standard garment. That is a manifestation of democracy. All men dress the same so that we cannot tell the class differences among them. That was how it arose.

Really it wasn’t until the mid-20th century, and really with the counter-culture of the 1960’s, that this idea began to arise that the natural man was the most manly man. That is a man who didn’t pay any attention to his grooming, who didn’t shave, who let his hair grow, and who didn’t care about his appearance. That came hand in hand with the valuing of nature, of back to the land.

Even before that, if you think of male icons of the 1930’s or even the 1950’s. If you think of Carey Grant, if you think of Sean Connery as James Bond, the masculine ideal there was not just a man who was competent and masculine, and also maybe violent like James Bond, but who was also sophisticated. Who wore a nicely fitted suit. Who shaved. Who knew something about opera and which wine to pair with fish. That was a masculine ideal. The idea that one could be elegant and sophisticated and manly at the same time. It kind of died in the 1960’s.

Again, as you think of human history, that’s just a tiny little blip. Of course now we’re getting back to the idea that men can be elegant and sophisticated and manly at the same time. I think finally the all natural movement of the 60’s and 70’s is dying.

Brett McKay: Wearing itself out. It seems like, and you talk about this in the book, as far as men’s style go, and style in general, it goes in a pendulum, right?

Russell Smith: Yeah.

Brett McKay: One generation will rebel against the other, so I guess the baby boomers were rebelling against their Brooks Brothers suit wearing dads, right?

Russell Smith: The parents, yeah.

Brett McKay: I know a lot of men who still think that. They’re still in that natural man mode. They think, why bother? Why is it important to care how you dress? Why do you think a man should care how he dresses? You make a case that I think is interesting. You say that our clothes are a form of art and gift to others. How so?

Russell Smith: Right. I think that you dress out of respect to people around you. You dress not just for yourself, but to make the people around you feel valued. If I am dressing carelessly or slovishly in the presence of people around me, it gives them a subtle, perhaps unconscious idea that I don’t take them awfully seriously. If I dress up to be in the presence of others, and by dress up I don’t mean I’m always going to be wearing a bow tie. I just mean that I dress cleanly and elegantly, as if I’ve made a choice for them. Then they feel valued and they feel respected.

That goes for events that you go to as well. If you dress well to go to a certain place, it shows respect for that place. On a more practice level, for one’s own … On a more selfish level, it helps one immensely to dress well in life because people seem to treat you better. They treat you differently and you can do this experiment. You can go to a police station wearing a hoodie and ask for help, or you can go wearing a suit and tie and ask for help, and you’ll see what happens. People wearing a suit and tie are treated with more deference, they are treated with more respect. People come to them to take the lead in a crisis. You may deplore that. You may think it’s a bad thing, and maybe it is, but still we could use it to our advantage.

Brett McKay: You work from home I imagine. Do you get up and wear a coat and tie every day?

Russell Smith:     , I don’t. I’m wearing a hoodie as I talk to you right now in my study. It’s funny. I crave an excuse to wear nice clothes. I do. I have an opposite schedule from everybody else because I work at home. What happens is when I’ve finished my work day at 5 or 6:00, that’s when I shave and shower, and that’s when I put on a jacket and tie and I go out. It’s kind of the opposite of everyone who’s coming home at that time taking that off. I very much look forward to that moment.

There’s a great anecdote. It’s a scene in Heart of Darkness, by Joseph Conrad. When the narrator is first progressing down the river into the jungle in Africa, and the foliage starts getting dense, and the heat starts getting oppressive, and they start leaving civilization behind. They come to the last outpost of Belgian civilization. It’s a telegraph hut. A telegraph operator in the jungle, deep in the jungle employed by the Belgian colonists. He comes out to meet the boat. He lives alone in this hut in the jungle, and he’s wearing a dark suit and starched collar and tie, in this intolerable heat. The narrator wonders why would he do that all day long there sitting alone in the jungle? The narrator reflects that in the vast degeneration of the land, was character. That’s kind of a funny European belief that I think is deep in all of us, that when we dress ourselves up as armor to fight off the decay and entropy around us. I kind of like that idea.

Brett McKay: I like that idea too. I feel too, not only when I dress up well, do others treat me differently, but I think of myself differently. I take myself a little more serious than when I’m …

Russell Smith: Yes, exactly. I’m happier. I’m just happier when I’m well dressed. I just feel I can deal with anything. I do feel that it’s a kind of armor that protects me.

Brett McKay: Right. There’s days, I work from home too so I’m typically wearing T-shirts and jeans, but when I’m in that mode like I got to get stuff done, I’ll dress up.

Russell Smith: It helps. There’s a psychological boost that it gives you. I’ll tell you something else too that’s important for men as they age to remember. I’m middle-aged. I’m 52 years old. I am very nervous about looking silly trying to carry off casual or hipster clothes at this age. I think that one’s ability to dress in casual clothes declines as one gets older, because one doesn’t quite have the perfect body, and doesn’t have the youthful glow. A clever T-shirt and running shoes is not as sexy on a middle-aged man with grey hair. I think that it really helps one as one grows older, to start moving into finer and finer quality and slightly dressier clothes.

I haven’t given up on social life. I still like going out to nightclubs where people are generally quite a bit younger than me. My god, I certainly still want to be attractive to young women, but I am not going to do it by dressing like a kid. If I’m going to go to a nightclub where people are largely going to be younger than me, I may well be the only person in a fitted navy suit and tie. That’s fine with me because then I am being exactly who I am. I’m not trying to pretend I’m someone else. People can say, “Oh, that’s the older guy.” That’s cool. I feel much more confident than if I’m simply trying to fit in with everybody else.

Brett McKay: Gotcha. Throughout the book, you mention sensuality as a quality that you should try to convey with your clothes. Which I think is interesting because whenever I dress, I don’t even think about, am I looking sensual? Why is that a quality men should be comfortable expressing?

Russell Smith: Yeah, it’s a tricky one because so much men’s fashion traditionally is against sensuality, right? The main goal of the standard men’s business suit is not sensuality, it’s to express sobriety. Which is a bit at odds. If you think of the dark colors that are standard in men’s suiting. Charcoal, navy, and black. These come from a long tradition of professions that are meant to express sobriety. If you think for example, of the priesthood. Priests from various religions around the world wear black as an expression of aestheticism and sobriety. A kind of distance from the pleasures of the world. In other words, an anti-sensuality.

Where in this uniform do we find a window in which to express sensuality? Well, in fabrics. The fabrics of a man’s suit are extremely soft and delicate and silk-like these days. In crisp cotton. In the little details, the tie in particular. The tie is such a weird thing. It’s such a useless, practically a completely useless garment, the tie. The tie has no practical role whatever. It is purely aesthetic. It actually evolved from a scarf.

In the 17th century, scarves were the simplest way for people to keep their shirts closed at the neck. Buttons were actually quite expensive. There were eyelets in the shirt, which you would pull over your head, the V-neck. Then you hold it closed with a scarf. People, particularly soldiers, started to develop more and more elaborate ways of tying these knots of their scarves so as to show off these knots. That’s where we get the origin of the tie. It gradually evolved.

Now we don’t need it to keep our shirts closed. We just need it because it’s the only bit of color, and a very feminine type of fabric, silk, in this otherwise closed off sober outfit. The tie is just this little window on your soul, because the rest of your body is completely covered up.

Brett McKay: What about … I guess pocket squares would be another way?

Russell Smith: Pocket squares would be another way. Socks. Cuff links. Of course, men’s shoes are so luxurious too. They’re extremely expensive and what you’re showing off when you’re wearing these shoes is a kind of hand crafted solidity. You want to show a little bit of luxury with your shoes, but in such a subtle way so people who don’t know anything about shoes don’t realize how expensive they are. They don’t realize what kind of labor that goes into them. That’s a very subtle expression of luxury.

Brett McKay: Speaking of shoes, you advocate spending a lot on shoes.

Russell Smith: Yeah, I don’t advocate spending a lot of money on clothes generally. I think one can get away with a very limited budget. I do, having lived as a free-lance writer for many years. Shoes is the one thing I don’t think you can skimp on, because shoes are really the fundament of your outfit. They’re like the root from which the whole outfit grows. Again, people who are class conscious, and that tends to be people who come from the privileged classes, although once you’ve noticed class differences it signifies, not people who don’t come from those classes. That’s the trick of it. They recognize certain symbols. They will note your shoes right away.

The other thing is, if you spend a lot of money on shoes they’ll last many years. They tend not to go in and out of fashion the way suit shapes do. It’s really worth your while.

Brett McKay: If a guy’s wanting to upgrade his wardrobe, what’s the go to dress shoe that he should probably make his first investment in?

Russell Smith: Okay, you need one pair of … Your very first shoe would be one pair of black leather lace up shoes. That’s an oxford style shoe. There are various variations on this style, but it should be as simple as possible. It could have a toe cap or not. My thing, and a lot of people think this is a bit too extravagant, but my thing is it must have a leather sole. The leather sole makes them expensive. That means they’re going to be probably over $250, maybe $300. The point about the leather sole is that people can recognize it. It looks good. You can put it on, take it to a cobbler and put a thin rubber layer over it, so that it never wears out. You can keep replacing that rubber layer. Those shoes will last you forever. That will be your first pair.

Now unfortunately black shoes are kind of going out of fashion, as you’ve probably noticed. More and more people with suits are wearing brown shoes. This has really been the style for the last 10 years. Your second pair of shoes should be brown or burgundy. They should also be plain. Although with brown shoes, the most ornate thing you could do is go to a brogue. A brogue is the shoe with the patterns made of punched holes in it. That’s called brogueing, or tooling. That’s called tooled leather. That would be probably your second pair.

Basically you need black and brown, leather soles, lace up. Your third pair would be a pair of slip on ankle boots, I would say. Like Chelsea boots, which are very useful for casual clothing.

Brett McKay: Okay, very good. What about suits? You lay out a suit ladder. A lot of guys when they’re thinking, “Okay, I got to get …” Most guys don’t have a suit. I’m surprised by this. A suit’s so useful because you can wear it to job interviews, or a funeral or a wedding. For an all purpose suit, for a guy who’s buying his first suit, what color should he go for?

Russell Smith: Right. There’s only two you can choose from. I’m giving you a choice of navy or charcoal. Charcoal is a very dark gray, not quite black. Either of those are appropriate for your first suit. You choose whichever you think matches your coloring best. Those suits are both very, very versatile. They could be worn in the day or in the evening. The reason I wouldn’t choose black is that black tends to look a little bit cheap. I don’t know why that is. It’s just not a very respectable suit color.

Brett McKay: It looks like Reservoir Dogs. Like the guys, right.

Russell Smith: Yeah, exactly. It looks a bit gangstery. It shows lint very badly, and if it’s shiny, and there’s just something wrong about it. I can’t quite put my finger on what it is. You need something that’s dark, but not quite black. Now it’s very important that your first suit be dark. Even if you live in a warm place like Los Angeles. I think that a light suit is not at all versatile and is going to look silly and casual in certain situations. A dark suit is much more versatile. Once you have two suits, once you have a navy and a charcoal, then you can move on to buying a summer suit in a lighter color. Don’t get light gray until you’ve really got a bunch of suits.

The navy and the charcoal can be paired with an almost infinite variety of shirts and ties. Again, black or brown shoes depending on how dressy you want to be. Traditionally, a black shoe is the most formal. Although even that is changing. Do you know recently here in Canada, we just had an election and a new prime minister was elected. He is a very young prime minister. He’s in his 40’s. He shocked everyone by going to his inauguration ceremony in a navy suit and brown shoes. I think this was the first time that it had ever been done. A lot of people complained that it seemed disrespectful and informal, but that’s the way things are going. It was a bit for us like the moment when John Kennedy showed up at his inauguration in 1961 without a hat. That was quite a daring step.

Brett McKay: It’s interesting, you talk about this in the book. This is going off the point of the history of men’s style, usually the changes in style are made by political leaders.

Russell Smith: Yeah.

Brett McKay: There’s a way you’re supposed to do things. I guess Windsor, he was the guy who propagated the Windsor knot. I forget, but one of the kings in England, he started wearing things a little more casually, and people were stunned that he did it. Then a year later, that’s what everyone was doing.

Russell Smith: Yeah. Probably the most famous example of that would be Prince Albert, Queen Victoria’s son, who became Edward VII. He was a daring guy and he behaved like a bit of a playboy. He went to race tracks and he hung around with actresses and Americans. People were interested in his lifestyle because he was something of a celebrity. People started following his clothing. Their house in Scotland, Balmoral, he loved to go spend a lot of time there because he liked to shoot and hunt. He started wearing plaid, which was a Scottish influence. Plaid became all the rage in Victorian England. Really because of Prince Albert. That’s why we have so much plaid in our wardrobes now. It comes from his adventures in Scotland.

He also had a little bit of a weight problem. He liked to eat a lot. He would wear a waistcoat, a vest as part of his suit, with many buttons. Apparently, at the end of his meals he would be so stuffed, he’d unbutton the last button on his vest. On his waistcoat. This became a fashion. To this day, we never do up the bottom button of our waistcoat. The same way we don’t do up the bottom button of our suit jacket. This is all Prince Albert’s influence.

The next would be King was Edward VIII who abdicated and became the Duke of Windsor, was a very, very popular fashion plate. The popular papers were always photographing his style. Of course, this was just the time when photographic magazines were first becoming popular. He was photographed everywhere, always wearing elegant, natty suits.

Both of those guys did a lot to casualize men’s clothing. They started toning down some of the more formal wear. For example Prince Albert, then someone would wear a white tie to dinner in the evening, and his long tail coat, and a white tie and a white waistcoat. The most formal outfit there is. At Balmoral he started having more casual dinners where he would wear a shorter jacket, and a black tie, which was very dressing down. That became the modern tuxedo. It was all going less formal.

Brett McKay: If royalty was the group that dictated style changes or fashion styles for men, what’s our royalty today? Who are the men that drive the changes in men’s style?

Russell Smith: Obviously, it’s celebrities. It’s popular entertainers. It’s singers, it’s actors, and it’s singers more than anything. There’s been a great revolution against convention and tradition, that’s really democratized fashion. The influences are coming from everywhere. I don’t think you can say there’s any one source that one looks to on how to dress. That’s better for the world generally in that it makes it a more democratic place with fewer class barriers. At the same time, it means it makes it a little bit more confusing for men who are trying to decide how to dress.

There are various movements going on that could only be described as conservatism that are dandy movements, that are encouraging men. African-American men, in particular in the United States, to espouse fine and conventional clothing, suits and ties and pocket squares in a very colorful and flamboyant manner. There’s an interesting movement in Africa going on right now that you’ve probably heard of called The Sapeurs. The Sapeurs were a group of very under-privileged men from the Congo who’d spent all of their money on hand tailored suits and ties in very bright colors, and leather shoes and all kinds of accouterments, like canes and hats. They look like very old fashioned dandy’s. It’s a form of social rebellion for them. It’s a form of kind of trying to move themselves out of the sense of lack of privilege that they have, to be noticed in the world. Those guys have presences in other European capitols like Paris in particular. There are all kinds of strange explosions going on right now. A kind of defiant interest in a luxurious and flamboyant way, of men’s dressing.

Brett McKay: You wrote this book a couple of years ago. Are you surprised by some of these changes that are happening, or did you see? It was like the writing on the wall?

Russell Smith: No, I’m not. I did say we’re emerging out of this period in which we value the all natural. We have started to embrace artistry and the art of this again. Yeah, I could kind of see this coming. I didn’t see coming, counter-movements like Normcore. There will always be a counter wave to anything like this.

Brett McKay: For our listeners who don’t … Normcore is when people dress like Jerry Seinfeld basically, right?

Russell Smith: Normcore. It may be a purely fictitious movement invented by the media. The idea of the metro-sexual was largely invented by the media actually as well. The actual metro-sexual was rarely seen in the wild. More in the pages of newspapers and magazines. I think the same goes for Normcore. The idea is that the most fashionable and cool of hipsters in the urban centers of North America, and particularly in Brooklyn, decided to reject fashion so completely that they begin to embrace a kind of anti-fashion, which involved deliberately ugly and bland clothes. To look not like a hipster, but like a tourist from the Midwest. With running shoes and plain jeans, maybe acid washed jeans and a T-shirt with a logo on it, and maybe a windbreaker. The idea of the blandest and most unnoticeable of all, that would be the highest fashion of all, and that’s called Normcore.

Brett McKay: Yeah, irony.

Russell Smith: Yeah.

Brett McKay: It just makes my brain hurt.

Russell Smith: Deep levels of cool. Yeah.

Brett McKay: I’m curious. What do you think the future is of men’s style? It seems like it’s been stuck. Sort of the same thing for the past 100 odd years. A little 100 plus years where it’s a suit, white shirt, tie. Are we ever going to move beyond that, or have we reached the apex?

Russell Smith: Isn’t that fascinating? I really don’t know.

Brett McKay: It’s really weird. You look at it, just like in the revolutionary times. They were wearing breeches and frock coats, and these very flamboyant things, wigs, and we’re done. I don’t know what, it’s gone decadence. I don’t know, we’ve reached the apex, and we’re just going to stick there.

Russell Smith: It’s very strange how long this has stayed without any change at all. That western standard, the western standard suit has spread to the rest of the world as well. It’s incredibly powerful and fixed. Fashion itself has been trying to fight against it for decades. You get high end fashion designers, runway fashion, every year doing shows in which outrageous and groundbreaking outfits are thrown down the runway. Men in completely crocheted outfits. Men in skirts. For how many years have you been hearing there’s about to be a revival of men wearing skirts? I’ve been hearing this since the 1980’s. I remember going to fashion shows. I lived in Paris as a student in 1985, and seeing men in skirts walk down the runway, and thinking, aha, finally men are going to wear skits.

Every 5 years, we see someone say it’s coming back, and it never, ever, ever does because fashion is always at odds with this very powerful force of convention, in the sense that a man must look a certain way in order to play a certain role. I don’t see that changing any time soon. I think that certainly our ideas of gender are slowly changing. Our ideas that gender is fixed and has to be defined in a certain way is slowly changing. Maybe we’ll see some more androgyny in men’s fashion in future years. I think that’s gradually happening, but not nearly as fast as anyone would have expected.

I don’t know the answer to that, and I can’t give it. I think you should go and buy suits now, they’ll be good for the next twenty years, I can tell you that.

Brett McKay: There you go. You talk about going back through the practicalities of style. You mentioned that you don’t advocate spending a lot on clothing. Should guys invest in a custom made suit or made to measure? If they’re buying clothes, should they not feel bad going to a good department store that has good brand suits there, and buying that and getting it tailored to fit, or should they go custom made?

Russell Smith: That’s a good question. Both are good. Nowadays in most cities, there are brand new businesses developing as we speak, and proliferating. Specializing in custom suits. What they’re doing is you’ll go and they will take your measurements. They will send those measurements off to Asia somewhere. It will either be China or Pakistan or Vietnam, where there are tailors working. They will cut a certain pattern, but to your size. It’s not all that different really from buying a suit off the rack. You’re not actually getting a suit that’s cut to fit you. You’re getting a slight modification on an existing pattern. It’s still a very, very good deal. Those suits are hardly more than suits off the rack from a good department store. I would say yes, that probably will fit you a bit better. It’s not a whole lot more expensive, so I would get yourself a made to measure suit.

The top end tailors tend to distinguish … They all have a different vocabulary, but here they tend to distinguish between made to measure and the bespokes. Made to measure means what I’ve just described. They’re giving to you a slightly different size of an existing pattern. The bespoke suit is something much higher end, and it’s where they’re going to start from scratch and draw you a suit and cut it for you. I know here in Toronto, a suit like that will start at about $5,000. That’s not what I’m talking about.

I would also say that there’s nothing wrong with buying cheap, quick fashion from trendy chains. Like Zara, or H&M, because it makes one feel good to have a natty suit that’s in fashion. It’s not going to last you forever. It’s not going to be the best quality, but that’s okay because the style is not going to last forever. I’m talking about suits that are going to cost you, say $300, $400. I think that if you’re strapped for cash, it’s really worth it to have one of those. Buy a new one every couple of years. Spend a lot of money on your shoes, on your shirt, and on your tie, and nobody will notice that you have a cheap suit on.

Brett McKay: Gotcha. Great advice there. Russell, besides writing about style, you also write short stories. Can you tell us a little bit about your latest collection of short stories and where the listeners can find out more about your work?

Russell Smith: Yeah. I am a novelist, and I’ve written several novels. My last novel was a book called Girl Crazy. My most most recent collection is a book of short stories, and it’s called “Confidence.” It’s about urban people who live in cities and have affairs and do terrible things to each other. It’s a funny and sad book. You can get it on Amazon. You can also check my website, which is

Brett McKay: Fantastic. Well Russell Smith, thank you so much for your time. It’s been a pleasure.

Russell Smith: It’s been a pleasure talking to you. Thank you.

Brett McKay: My guest today was Russell Smith. He’s the author of the book, “Men’s Style, The Thinking Man’s Guide to Dress.” It’s available on amazon. Com. You can find more information about Russell’s work at

That wraps up another edition of The Art of Manliness podcast. For more manly tips and advice, make sure to check out The Art of Manliness website at If you enjoyed this podcast, I’d really appreciate it if you’d give us a review on iTunes or Stitcher. As always, appreciate the support. Until next time, this is Brett McKay telling you to stay manly.

Related Posts