You’re More Stylish Than You Think You Are

Everyone, at some point, feels like they have an “off day”, style-wise.

Or conversely, everyone feels like some days their style is really locked in. Maybe you have a few of those days a week, but the other days just aren’t infused with the same kind of effort so the results are, in your mind, a bit below your usual standard.

Maybe on those off days you just throw on any old thing since you need to head out the door to run errands or drive the kids to school, or whatever.

What I’m saying is that it’s normal to feel like not every day is your “best” day when it comes to dressing well.

If I need to go into the office, I’ll coordinate an outfit the night before. I’ll make sure my pocket square plays well with the patterns of my jacket and shirt. I’ll make sure the socks that work best with my trousers are clean. I’ll check the weather to see what kind of outerwear (if any) makes the most sense.

On those days, I feel like a million bucks. On those days, I KNOW I look good.

But there are other days where I don’t put in nearly the same amount of thought or effort. On those days, I grab whatever is clean and presentable and head out the door. Ok, maybe I think about it a little bit. But those are definitely not days when I would necessarily snap pictures of myself for use in my “Outfit Of The Week” articles.

I imagine many of you have days like those, too. And, sometimes, I imagine you lament not being able to show off your “best” self to the world.

On those days you probably don’t feel all that stylish. Those feelings are normal but the existence of those feelings might make you feel like a bit of a style fraud!

But I’ll let you in on a little secret…

You’re more stylish than you think you are.

That’s right! You are much more stylish than you probably think you are! How do I know that? Well, if you have even a slight inclination toward menswear or dressing well, you probably already have the bare minimum covered.

The other day, I had one of my “off” days. I had to leave the house early to get my son to school so I threw on a pair of khaki pants and boat shoes (it was warm that day) and a denim shirt.

For me, that outfit took zero thought whatsoever. The pants were my $30 chinos from Lands’ End and my shirt was the same denim shirt I wear all the time.

If I took a step outside myself and looked at my outfit, there wouldn’t be anything striking or noteworthy about it.

But for someone else, I probably looked pretty dialed-in, stylistically speaking. They might have looked at my worn denim shirt and thought, “Wow, that shirt is pretty cool. I wish I had a faded denim shirt like that. That guy looks good!”

And I imagine the same thing happens with you on your “off” days. The things you pull on in the morning when you aren’t thinking about it probably register on everyone else’s mind as pretty stylish simply because you probably already have a strong sartorial foundation on which you’re working. You probably have a pretty solid wardrobe of classic men’s staples. You have probably spent a little bit of time honing your style to the point where anything you put on “works” without you having to think much about it.

And that’s amazing! That’s what everyone should be shooting for.

But how did you get to that point? How did you get to the point where you can blindly reach into your closet, pull out a shirt and some pants, toss them on and look put-together (and yes, you DO look put-together, even if you might not feel like it)?

Well, I suspect you probably took your time and slowly built an interchangeable wardrobe based around staples that don’t go in and out of style.

You’ve also probably gotten used to wearing those staples in all sorts of scenarios. You have trained yourself, unwittingly and over time, to feel comfortable wearing things like chinos instead of sweatpants and collared shirts instead of t-shirts.

The people around you got used to it as well. Maybe years ago you received snarky comments about being too “dressed up”, but now your family and friends know how you dress so they don’t think anything of it anymore.

Once that started to happen, you might have culled things from your wardrobe that you no longer had use for, or at least relegated those pieces to only their intended functions (like wearing gym shorts only for exercise, for instance). That paring-down of your closet has removed the choice to wear that “un-stylish” stuff. Wearing sweatpants out of the house in a “non-working out” scenario simply isn’t an available option for you anymore.

At this point, you’re in a very GOOD place, style-wise. You’re probably viewed as pretty well-dressed by people who know you. But because it’s become habit or somewhat second-nature for you, your “no effort” days still register as pretty, darn stylish by all external observers!

Now, this article is NOT an instance of me trying to brag and say “Oh, I’m still SO stylish even when I’m not even trying!”

What I AM trying to say is that you should feel happy and confident even on the days when you feel like you didn’t really give it your all. For a lot of us, how we dress is intimately tied up with our personalities and our self-worth, so we might sometimes get down on ourselves when we feel like we don’t look our best.

It’s no different than an athlete feeling down because he could only do an hour workout instead of two hours. In those moments, he might not feel his best, however everyone else looking at that guy would still be like, “Wow, you’re so fit and healthy and a real fitness inspiration.”

The standard that that athlete has set for himself is higher than most other people’s. So, his “off days” are still pretty good in everyone else’s view. It’s the same for YOUR “off days” when it comes to your style.

You are more stylish than you think you are! So, remember that today and let it make you smile.