What Most Guys Get Wrong About Comfortable Clothing

"You know I’d put more effort in, but I just love comfortable stuff."

Clients tell me this all the time when they get on a call with me.

Beyond being a guy myself, because we work exclusively with men, we have a unique perspective on what men actually want. It's this:

We want to be comfortable.

And most guys think because of that, they should just give up on style.

What most guys don’t understand is that style and comfort aren’t mutually exclusive.

They can, and do, coexist beautifully, especially these days.

I'll show you how in just a second.

More brands are realizing that if something feels good, men are far more likely to buy and actually wear it.

Hardcore menswear guys complain about stretch fabrics, calling them "unpure." I used to feel the same way. Now? I say, who the hell cares? If it looks good and feels great, I’m in.

I learned this the hard way with selvedge denim. I was obsessed—the craftsmanship, the look, the heritage. The problem? I never actually wore them. Every morning, I reached for a more comfortable pair of pants.

You have to actually want to wear your stuff. Part of the drive to do that is feeling comfortable in it.

Most guys don't realize certain stylish clothing can indeed be comfortable, so they don't even try.

Drop the idea that you have to choose between the two. You don’t.

The clients we work with get to prove this every day, and so does my own closet. The goal is to shoot for both.

Think of it like nutrition. A good nutritionist will fill your pantry with stuff that tastes good AND is healthy, and you’ll look good and actually eat the stuff.

We do the same - Fill your closet with stuff that looks good AND is comfortable, so you’ll look good and actually wear the stuff.

You CAN have both.

Merino Crewneck Sweater from Theory

Here’s some tips on how I do it, and what we do for clients when they want to prioritize comfort.

I wear wool blends a lot. And no, wool isn’t just for winter. There are plenty of lightweight wools and wool blends that work great in summer and spring.

For tops, merino wool, like this crewneck is made from,  is my go-to—it’s naturally stretchy, temperature-regulating, and works in almost any environment.

Modal and Tencel blends are also great because they’re soft, breathable, and have just the right amount of stretch. These are typically much more comfortable than the average cotton shirt you wear, such as this polo.

If I’m looking at something made from cotton, I always check the fabric details and try to find something with a little elastane or spandex. A small amount—just 2-5%—adds movement and flexibility without making it look like gym wear.

This one tweak makes a huge difference in how comfortable something feels. This, to me, is especially important in pants, as when you sit down, it allows the pants to give a little - which I like in wool trousers as well.

Another easy change is lace-less shoes. Lace-ups are just a bit less likely to be worn.

For example - Most of our clients love lace-up boots, myself included. The problem? I almost never wear them. When I'm getting ready, I forgo the small amount of effort to lace them up when I have easier options right next to them. Chelsea boots fix this—same look, but they slide right on.

For sneakers, I wear these several times a week - they're one of the most comfortable shoes I've worn and have been worth the cost.

In the summer and spring, we're opting for drivers or loafers that slide right on.

Driving Moccasins from Suit Supply

The soles of your shoes also matter more than you think. A lot of traditional dress shoes and boots come with stiff leather soles that feel terrible after a few hours.

If comfort is a high priority for a client, we always look for a subtle rubber-blend sole instead. It’s more flexible, absorbs impact better, and keeps things comfortable without looking too casual.

Finally, let's talk about fit. If one more guy asks me whether clothing should be tight or loose based on a trend, I might lose my mind.

Clothing shouldn’t be tight. It shouldn’t be loose. It should just fit.

Saying something is tight or loose implies that it doesn’t actually fit.

That’s like asking if your shoes should be too small or too big. Neither—your shoes should fit your feet, just like your clothes should fit your body.

When clothes are too tight, they feel restrictive and stiff. If they're too loose, they'll sag, shift around, and bunch up in uncomfortable places. Both issues cause you to be uncomfortable.

There are plenty of other small details that can make clothing more comfortable—stretch panels, seamless stitching, elastic waistbands, raglan sleeves, etc.—but if you start with the basics above, you’ll be in a much better place.

Like all the products I recommend in these emails, I'd recommend not going out randomly to buy the examples listed above.

The whole reason we exist is to help you get clothes that actually work for you, not just throw out generic suggestions.

You need to know what colors look best on you, what fits your body type, and what aligns with your personal style and lifestyle, including your job, climate, and hobbies. Style isn’t just about looking good. It’s about making smart choices that fit you.

If you want us to show you what actually works for you, build you a wardrobe that all pairs together, and make the process simple and stress-free, check out our in-person or online personal styling program, where we handle all of this for you.

Or just apply for a call with me personally. We’ll go over where you’re at, give you a strategy to look great, and see if we’re a good fit to help you.

Hope that helps.

x Patrick