I have been watching and loving your stand up and TV series for years so I was shocked, shocked when you came on stage during your new Netflix special wearing a suit. This is a big deal for me because it reminded me of my own transition, years ago, to dressing like a grown up. I’ve read how you recently made this decision and I seriously applaud you for it. But this is also a big deal for people who couldn’t care less about classic men’s style. Some wondered if you were going to be more conservative or boring because you had suited up, like it had somehow poisoned your blood. It’s amazing the vestigial feelings a suit can conjure up; I think that’s one reason why a lot of guys are afraid of wearing suits or “dressing up.” But what you’ve proven is that anything we wear is a uniform and suits are no less individualistic than black tshirts and jeans.
But, and you knew there would be a but, the suit you wear in the show suffers from many of the issues I also encountered when I started trying to dress well. I know you didn’t ask for this, and I hope you don’t mind, but I want to offer my advice on how to wear a suit better, so you not only look good but feel great. And I’m doing this in a public way because this is stuff a lot of guys need to know more about.
First off, I think you fell into the same trap so many do, that all you need to dress well is a suit, any suit. Jacket, trousers, shirt, tie, shoes. But what happened to me is that I couldn’t see the trees for the forest; I couldn’t see that the details weren’t working as well as they should because I was overwhelmed, in a good way, with seeing myself in a suit.
To cut to the chase, the suit you are wearing doesn’t fit well. The sleeves are too long, the shoulders are too wide and the trousers are too long. Did you notice, just minutes into the show, that big gap where your jacket is hanging off your shirt collar, a la Sean Spicer? Or the way your shoulders buckle slightly and the ends droop over your arms? Your sleeves could lose half an inch or more, which would allow people to see your shirt cuff (which frames your hands nicely) and not make the jacket look like an overcoat. And if your trousers were hemmed, they wouldn’t pool all over your shoes and instead would fall smoothly, therefor not drawing people’s eyes to your feet.
But I’m not going to avoid one of the issues with guys like you and me wearing suits: we are middle aged and a bit larger. And typically the solution some suit salesmen have is to give us big suits, to try to hide our size. It doesn’t work. In fact it has the opposite effect. At the other end of the spectrum is the trendy “slim” suit. While that might be flattering on a 20-year-old, it doesn’t work for us. I’d also warn about another current trend that your suit is suffering from, low-rise pants; they force your belly out, making it look bigger than it is, and making you want to unbutton your jacket, which only brings your mid-section into better view (and you want people looking at your face, not your belly). By getting pants with a higher-rise (no, not up to your nipples) you smooth out the middle section while making it look like your legs are longer. I’d go so far as adding suspenders instead of a belt: belts cut into your midsection uncomfortably and draw the eye to your belly. If you do go for suspenders, just keep them out of sight behind your jacket, you don’t want to look like Mork from Ork.
So if I’m saying your current suit is too big but you shouldn’t go for slim suits, what option is left? You need to go somewhere in the middle, with a suit that actually fits you. Since you have the means (I assume) I’d strongly suggest you go custom if not bespoke. I know it’s hard to find top quality in North America, and the process can be daunting, not knowing exactly what to ask for, but the tailors are out there. And when you find one, you can have a suit cut to your body, not have to force your body into someone else’s suit. The best thing is, you can make sure a custom tailor cuts a suit made to be moved in – in fact, do part of your act in the measuring room and that way the tailor can make sure the suit doesn’t lose its shape as you move around and gesticulate wildly about… well… you know.
Sadly, some people are saying mean things about your suit – that it makes you look like a funeral home director, for example – but I want you to understand that that has to do with the details of your suit, not wearing a suit in general. As much as the contrasting stripes add a touch of flair, the overall dark colour is more formal and sombre, things that you are not. Now, I’m not saying start wearing green suits, but lighter shades (like the mid-blue one you wore on Fallon) make you look stylish and more relaxed.
I’m also going to stray a bit from just your suit. I would recommend getting a well-made, custom shirt that fits comfortably at the neck so that you don’t have to unbutton it. Sadly, an unbuttoned collar/loosened tie can make a person look like an overworked businessman. Trust me, a custom shirt can change your life – and make you look one hundred times better. The tie is also a bit too business for my taste. There are so, so many options out there but perhaps start by looking for texture, like a grenadine tie (don’t worry, they’re not weird, Bond wears them.) I’d also encourage you to get some dark brown shoes. Black is ok but it can look a bit formal and again business-y. And you’re not a businessman. As the men’s style writer Alan Flusser says, lay anything on a Mahogany table and it looks good; brown shoes finish off almost any colour of suit nicely.
I really hope this helps. The last thing I want is for you and other guys who aspire to dress well to be discouraged by all these details. But trust me, once you invest a bit of time getting to know how things should fit and how to judge quality, then you can get on with your life just looking great and feeling confident. What I really want to avoid is people having a few bad experiences with suits – not looking as good as they thought – and assuming they just don’t look good in suits. You do look good in a suit, I just think you can look better.
And finally, thank you for showing the world that someone can still be profane, hilarious, insightful and challenging even if they aren’t wearing a tshirt and jeans.
All my best,
p.s. And hey, it’s not all about suits either; a great sport jacket and open-collared shirt can look pretty damn grown up too.