Wear What Makes You Feel Good. But What Does “Good” Actually Mean?

“Wear what makes you feel good.”

Makes sense, right? We all want to feel good. And different kinds of clothes make different people feel good.

Some people feel good in classic tailoring. Some people feel good in streetwear. Some people feel good in workwear.

We all have our niches. We all have the kinds of clothes that feel like “armor”, as in: they feel so good and natural on us that we feel like we could take on the world. We feel like our best selves in them.

So wearing what makes you feel good is a really good piece of advice. Life is short, after all, and this isn’t a dress rehearsal!

The only problem is that it’s often hard for men to determine what “good” actually means.

But in order to get a really accurate handle on your style, I believe it’s important to define “good” for YOU.

Whenever I see or hear people ask “how do I start dressing better” I always start with telling them that they first need to decide what they want to “say” to the world. I wrote a whole article on this not too long ago.

In my case, when I first realized I needed to stop wearing hoodies and sneakers to work, I decided I wanted to say to the world that I was indeed an adult who could be trusted. I was mature. I was capable.

So, I began wearing clothes that conveyed those things. I wore khaki pants and sweaters and tweed jackets and stuff like that.

Dressing like that elicited positive feedback, which made me feel good about myself. I felt comfortable walking into corporate interviews and nice restaurants. I felt confident that I was always appropriately dressed. I liked the way people looked at me and treated me.

But another thing that I always liked about my particular style, which emphasized things like sport coats, boots, leather jackets, and rough sweaters, was its utility. In things like flannel shirts, wide brimmed hats, or trench coats, I always felt ready for action in whatever I had on. Yes, my style leaned classic, but there was always a sense of practicality in my style. I felt like I could tackle whatever the day threw my way.

Handsome yet tough. Respectful yet unafraid. Elegant yet unfussy.

Simple. Understated. Manly.

THAT’S what “good” means to me!

When I wrote an article a while back on the things women want to see you wearing, my wife told me that one of the things that women love so much about men in classic menswear is the “unmistakable manliness” of it. A twenty-year-old girl can wear a hoodie and sneakers, but she isn’t going to be wearing a tweed sport coat over an oxford shirt.

So, for me, feeling “good” in what I put on means feeling like man. Capable. Mature. Responsible. I feel like the clothes I choose make me come across in those ways.

But what does “good” mean to you?

Does “good” mean “responsible”? Maybe it means “edgy” or “tough”. Maybe it means “invisible” or “accepted”. Maybe it means “sensitive” or “approachable”.

There really isn’t a right or wrong answer here. But having a really clear definition of “good” will shine a light down your sartorial path.

How does defining GOOD help people find their style?

Well, we already examined how I use my definition of “good” to refine my own style. But let’s do another one.

Say feeling good to you means feeling “accepted” by your peers. If you work in midtown Manhattan, maybe that means wearing navy chinos, tan shoes, a gingham shirt, and a fleece vest. Would wearing that ensemble make ME feel good? No. But for someone who wants to adhere to a rigidly-defined corporate culture it might make them feel like a million bucks.

Maybe feeling good to you means feeling “youthful”. In that case, I could see things like vintage t-shirts and Chuck Taylors making you feel like your best self.

My point here is that once you realize that you should wear things that make you feel good, you need to actually drill down into what exactly that means for you, otherwise you won’t have any clear direction for yourself. Without that clarity, you’ll waste time trying things that you see other people wearing (the things that make THEM feel good) and wonder why they don’t quite work for you.

So, what does “good” mean to you?