5 Reasons You Don’t Yet Feel Comfortable In Your Style
I’ve been interested in menswear for a while now.
Once I switched over from “not caring at all” to “caring”, my sense of style, not surprisingly, shifted pretty dramatically.
In the years between then and now, however, my style hasn’t really changed all that much. Collared shirts, chinos, boots or boat shoes, sport coats, leather jackets, hats of all types. If I had to describe my style, I would probably just call it “classic”. I’m not sure “ivy” or “trad” really hit the mark, although I enjoy OCBDs and loafers as much as the next Northeasterner.
The point I am trying to make is that I don’t feel like my style has gone through massively different iterations as I progressed through the years in my sartorial journey. Yes, I have found pieces I wear all the time and have become part of my permanent rotation. And yes, I have jettisoned things that just didn’t work for me. But it was all some sort of variation of a similar theme.
Instead of the word “evolution”, I would say that my style has solidified or calcified. I wrote about this a bit a while back when I was analyzing how the pandemic helped shaped my style.
All the “pieces” were there already, they just needed to fall into place.
Even though my style hasn’t changed too much over the years, I remember not feeling entirely comfortable with my style until fairly recently.
I felt self-conscious a lot of the time. I felt that maybe this piece or that wasn’t really “me”. I felt like I was maybe trying too hard.
I was enjoying the journey, but there was always a little twinge of uncertainty. There was always the feeling that I was right on the cusp of feeling confident, if only I could find the right shirt/pants/jacket, or whatever.
Do any of you feel the same way? Maybe you have a pretty good handle on the type of clothes that make you feel good, but you feel you’re falling a bit short of that cool, easy comfort that defines truly stylish people. You feel, while definitely well-dressed, like you just aren’t quite there yet, style-wise.
Why is that?
If that sounds familiar then read on for the five reasons you don’t yet feel comfortable with your style.
#1 – You have/buy too much stuff.
Let me know if the following sounds familiar.
You have a decent wardrobe, but you keep seeing things that catch your eye. Maybe a new pair of boots. Or a different variation of a shirt you already have. Or a casual jacket that fills a slightly different niche than all the other casual jackets you already own.
There’s nothing wrong with being attracted to that stuff. That impulse you feel to pick up something new is what makes the whole economy go round.
The problem is that buying more stuff and always being on the hunt for something new will work against you if you’re trying to find comfort and ease with your own style.
Why is that?
Well, because the more stuff you have, the less you wear and appreciate the stuff you already own. There are only so many hours in the day and so many days in the year. If you are constantly adding to the pile of clothes you already own, nothing really feels special because you don’t spend enough time with any one thing to grow attached to it and have it become part of you.
Buying something new is not going to make you feel more confident in your style. Thinking, “Oh, well if I just had that then I would be truly stylish” is misguided. The wanting and the hunting for something new will leave you feeling dissatisfied with most of what you acquire. Sure, there will be a few things here and there that you will love and cherish and they will become part of your permanent style, but those things are few and far between. Mostly, all that stuff you buy will be forgotten.
So, try your best to tamp down the impulse to buy more stuff. It’s more difficult to feel comfortable in your style when you have a whole closet stuffed with different things to choose from than if you have a small, thoughtfully curated wardrobe.
#2 – You chase trends.
Off the top of my head, here are some menswear trends from the past few years…
Birkenstocks, tie-dye everything, Crocs, man-purses, cargo shorts, carpenter pants, bleach-blonde hair, joggers, pool slide sandals, tote bags, Gurkha trousers, and chore coats.
Let’s not forget the more “macro” trends like super skinny suits.
You can never keep up with trends. Trends sell products. You’re not supposed to follow every single one. If one comes along that speaks to you and works for your preferences, fine. But jumping from one to the other ensures you’ll never truly feel comfortable in what you’re wearing.
Instead, try to find clothes that defy trends. That means middle-of-the-road proportions and items that have stood the test of time.
#3 – You’re too focused on the clothes, themselves.
I know it seems odd to include this one, since this site is about clothes, but keep this in mind…
The clothes are not the point. The clothes are not the adventure. The clothes ACCOMPANY us on our adventures.
You’re not going to feel comfortable in your new fedora until you wear it in the pouring rain on your commute. Or through the driving snow on your way to the new restaurant for a date with your wife.
Those new boots will just be a regular pair of boots until you’ve hiked up a mountain to have a picnic with your family.
That tweed jacket will just take up space in your closet until you fold it up to serve as a pillow on your next flight.
The adventures on which we take our clothes are what make the clothes special. If you are too focused on the clothes, themselves, providing you with satisfaction, you are missing the point. And you’re depriving yourself of letting the clothes serve you as they are supposed to.
A nice suit is just a nice suit… until it lands you a coveted job. Or you wear it on your anniversary dinner.
Use clothes as tools to help you navigate life.
Once you start viewing clothes in that way, you will feel much more comfortable in them.
#4 – You’re trying too hard to please people.
In one of my previous jobs, I worked in menswear marketing and was delighted that I could wear a suit every day and not get weird looks from my coworkers.
Unfortunately, I used the suit as armor to cover up my own perceived short-comings. I was well-dressed, but I was rigid and fussy about it. I most certainly was NOT stylish. It turns out, I was desperately trying to please people. I felt like if I didn’t dress to the nines every day, then everyone would see through me.
What I didn’t realize at the time, was that certain people will never be pleased with you no matter how hard you try.
So, don’t waste your time.
Trying to please people means you’re never truly dressing for yourself. And if you’re not dressing for yourself, you’ll never feel comfortable in your own style.
#5 – You lack overall confidence.
This should be the most obvious.
You’re never going to feel comfortable and stylish if you have no confidence.
Do you eat like crap? Do you neglect physical fitness? Do you deprioritize sleep? Are your relationships running on autopilot?
If so, no wonder you can’t home in on your style. Clothes are not going to paste over your crappy self-image and magically make you feel good.
Clothes can definitely HELP you feel more confident, but you can’t just paint over rotten siding.
Try this simple experiment: Do a vigorous workout and then put a t-shirt and jeans. Don’t you feel more like Marlon Brando than you did before?
A boost in body-image will make you feel ten times more stylish in even the simplest, most casual clothes.
When I think about the items in my wardrobe that make me feel the most stylish, they often aren’t the newest, or the most expensive, or the highest quality.
They’re the things that stir up memories. Memories of reading to my sons at bedtime, or lounging by the fire on a cool summer night.
My advice to you, if you feel like you’re struggling to feel as good as possible in your clothes, is to slow down, stop searching for the next best/trendy thing, and create some awesome experiences with the people who matter most.
Whatever you’re wearing at the time will feel like “you”.
