How To Maximize Comfort While Wearing Classic Menswear

The weekend before last was Father’s Day.

I had a fantastic day. I slept in and woke up to eggs Benedict and champagne. I played with my sons. I got some writing done. Once the kids were in bed my wife made a fabulous dinner of French onion soup and steak with crème brulee for dessert.

On special occasions my wife and I like to get dressed up for dinner even if we are staying in. It helps a special day feel even more special.

My wife wore a lovely blue dress. I wore a double-breasted jacket, tie, French cuff shirt, and tartan, wool trousers.

Between dinner and dessert, she and I relaxed in the living room with some wine.

It may have been the booze, but I was so physically comfortable in that moment. It got me thinking about something I hear quite often in response to why people don’t dress in more traditional menswear these days.

“It’s too uncomfortable.”

Or some variation of that.

There seems to be this pervasive myth that classic menswear is somehow restrictive and uncomfortable.

My goal is to dispel that myth and to provide tips for ensuring you always feel comfortable in your tailored clothing.

Traditional, tailored menswear is not inherently more uncomfortable than casual clothes. Often, I find the opposite to be true.

For me, it comes down to two things, primarily: material and fit. Let’s unpack material first.

The other night, my jacket was a thick, soft worsted wool in a twill weave. Wrapped around me, it almost felt like a thick flannel shirt.

My French cuff shirt was a smooth, icy cotton poplin which kept me nice and cool.

The trousers were soft wool, like the jacket.

My tie was a silk grenadine.

So, wool, cotton, and silk. They all felt soft and even luxurious to the touch. Sure, I could have been in jeans and a t-shirt, but objectively speaking, would that make me feel markedly more comfortable?

The answer is no.

Now, perhaps if my jacket and shirt were cheap polyester… or if I was allergic to wool. Or maybe if the wool trousers were scratchy and unlined.

In those cases, yes, of course my clothes would be uncomfortable. But the same could happen with casual clothes.

Now, let’s talk about fit.

I normally purchase a size 42 regular jacket in a “classic” or “relaxed” fit, since I feel like there is more wiggle room when it comes to tailoring. One of the first things I do when I try on a new jacket is raise my arms up as if I am putting my elbows on a desk. If it feels too tight across my back and shoulders, I know the fit isn’t for me.

The jacket I wore the other night is roomy enough to feel comfortable no matter how I am moving (within reason of course). Could I comfortably throw a football or do a set of pull-ups in it? No. But you can’t do squats in a pair of jeans, can you? Would you say that jeans are uncomfortable because you can’t perform literally every single physical task you can think of while wearing them?

The shirt, like the jacket, is roomy enough to allow for ease of movement, but certainly not so roomy that it would look sloppy if worn by itself. They real key to a shirt’s comfort is room in the body so that the buttons don’t pull, and a properly fitting collar. If your collar is too tight, you’ll never feel comfortable.

Here is a good rule of thumb for getting the right collar size: You should almost forget that you’re wearing a tie. That’s how it should feel. You shouldn’t feel as though you have something wrapped around your neck. If you do, your shirt collar it too tight or you tied your tie too tight.

For the trousers, there is room in the waist and the seat. But, again, not sloppy at all.

So, if your fit is on point, there shouldn’t be anything pulling, pinching, or constricting.

At this point, it is clear that, when looking at material and fit, the assertion that casual clothes are inherently more comfortable than traditional, tailored menswear does not hold water.

Now that that’s out of the way, what steps can you take to ensure you feel maximally comfortable in your suit, sport coat, or what-have-you?

#1 – Pay attention to material and fabrics.

Unfortunately, this means ponying up a little more money to get high-quality clothing.

A higher-quality suit is going to feel softer and more comfortable than a cheapy, bargain basement version. This shouldn’t come as a surprise, since the same concept applies to your casual clothes, too.

#2 – Make sure your jacket fits your shoulders.

As you know, pretty much anything else on your jacket can be adjusted with the exception of the shoulders.

Put the jacket on and move around a bit. Does it feel too tight? If so, then it probably is. Size up and see how THAT feels. It’s the same thing you would do with a pair of jeans.

Once you find a jacket that feels comfortable, take it to a tailor, pay $50 and your jacket will fit like it was made for you.

#3 – Make sure your shirt collar fits.

This is probably the most important point to keep in mind. As I said earlier, if when you button up your shirt collar and put on your tie you feel like something is wrapped around your neck, your collar is too tight!

You should be able to close your eyes and imagine you aren’t wearing a tie at all. That’s how it should feel. Don’t cinch your tie like a tourniquet and you’ll be surprised at how comfortable a tie can be.

Now, don’t go too far in the other direction and start wearing collars with giant gaps. But you knew that already. My point is simply that a buttoned collar and tie is only uncomfortable if you make it that way.

Honestly, I feel more strangled when I am wearing a hoodie and have a giant puffy hood hanging off the back of my neck.

#4 – Go easy on the waist.

There’s no need for vanity here. Size up a little in the waist if you need to.

Proper trousers, especially if you wear suspenders, don’t fit like jeans. They are supposed to have a bit of room in them so that they are…say it with me… comfortable.

I wear a belt as much as the next guy, but once you try your dress pants with suspenders, you might never go back. They are supremely comfortable. All you need to do is, when you take your trousers in to get tailored, request to have suspender buttons added. It’s so simple.

It’s important to remember that the suit as we know it was originally called the “lounge suit” because it was a more comfortable, casual version of menswear of the time.

Sport coats and blazers were used for active pursuits.

These pieces were designed for comfort.

And they ARE quite comfortable. It’s just that men have been brainwashed into thinking they aren’t. In reality, men just aren’t used to wearing those items anymore.

So, it’s not that they feel uncomfortable, they just feel different. Different from what men have become used to.

I promise, once you get accustomed to wearing tailored clothing, you’ll feel totally at ease.