On long drives, I like to let my mind wander.

Sometimes I might sing along to some old Broadway CD I have kicking around, or listen to some strange feature on NPR, but a lot of the time, I’ll just revel in the silence and allow my thoughts free rein.

The other day, it occurred to me that clothes are kind of like windshield wipers.

Let me explain…

I own two vehicles. Our older one (our SUV) is from 2012. It has a grand total of four speeds for the wipers… off, low, medium, fast.

Our not-quite-as-old vehicle (our truck) has roughly ten wiper speeds. I say ten, but it could be eight or fifteen. Honestly, I have no idea how many settings it has. All I know is that it has way more than I need.

When I flip on the wipers in my truck, I have no clue what speed I am selecting. I have to click through half-a-dozen settings before I land on one that is appropriate for the level of precipitation.

And it’s kind of a pain in the ass!

I always think, “Do I really need all this choice?”

“Do I need my wipers to function at ten different split-second increments?”

“Is one wipe every second sufficient, or do I need one wipe every 1.1 seconds?!”

With my SUV, I don’t have that problem. If it’s raining hard, I choose the fast setting. If it’s not raining hard, I choose medium. I hardly ever use the low setting.

So, with my SUV, it’s basically “Is it raining? Yes? Then turn on the wipers.”

It’s very simple.

And that’s kind of how I feel about clothes.

I have written a lot before about how too much choice makes it so you don’t really ever WEAR the clothes you have. And it makes sense. If you have 50 shirts, and you wear them all, you can only really wear one particular shirt a couple times a year. In that scenario, you’ll never really develop any sort of real connection to any one shirt. You aren’t going to build memories with it or be “known” for it. You might even forget you own it until you dig it out of your closet every now and again.

I always marvel at guys who get excited about “patina” yet they buy new clothes every week. Patina, creases, fraying, fades, scuffs, and all the other markers of longevity and adventure only come when you actually WEAR things. If you have too much stuff (because you buy too much stuff) then you’ll never get there with anything.

Everything in your closet will always look crisp and new. You won’t have anything that’s truly special to you.

So, what are you to do if you’re like me and you have accumulated a lot of stuff over the years? For someone who loves (and writes about) clothes, I honestly don’t have THAT much stuff, but I have more than the average guy. And more and more stuff (even stuff you love) naturally piles up as time goes on.

I think the key is to be intentional with when you wear your different items. Take jackets, for example. I have a bunch of jackets and coats, and if I wasn’t careful, I wouldn’t be able to wear them all in one season. But I designate specific times in which I wear each item in order to make sure I wear everything in almost equal rotation.

I have my jacket for when it’s raining (Barbour). I have my jacket for when it’s a little warm out but I still need some protection (Harrington). I have my jacket for when I want to look cool (leather biker). I have my jacket for when I’m ferrying the kids around and it’s cold (leather flight). I have my jacket for when I’m chopping wood (barn coat). I have my coat for when I’m heading into the office in the fall (trench). I have my coat for when I’m going to the office in the winter (overcoat). I have my coat for when the temperature drops below freezing and I’m outside in a casual setting (wool hunting coat).

Many of those pieces could be worn in a lot of different circumstances. And that would be totally fine. But for someone like me who has a lot of fun stuff, I make sure I am intentional about when I wear each item. Not only does that make it so that I get a lot of use out of everything, but establishing specific scenarios in which I wear each piece reduces the amount of choice I face.

It’s raining? I wear the Barbour. Simple.

You get the idea.

But getting back to the wiper analogy… in my SUV, deciding whether I need medium or fast wiper speed is a simple decision. When I am in my truck and deciding between a dozen options, I get annoyed. I am constantly adjusting the speed because I CAN. I know I have the option of something different so I am very rarely satisfied with what I have.

I feel that that’s a pretty universal feeling. When you have a lot of options, you constantly second-guess whether or not you made the right decision. On the other hand, if you can only choose between two things, you relax knowing you probably made the best choice from what you were presented.

The shades of grey are where people get anxiety. And I think that contributes to some men feeling uncomfortable with clothing in general.

They have their jeans, t-shirts, and sneakers and pull on the same variation of one outfit every day of their lives. When they start thinking about branching out into improving their wardrobes, they’re then confronted with the unease of having to make CHOICES!

When they owned one pair of jeans and 3 t-shirts, the decision was easy and stress-free. Now they have more clothes and they need to decide how to combine them. There is much more room for the nagging “did I make the right choice”?

Add in that clothing is an experiment made in front of everyone you interact with during the day, and getting dressed all of a sudden becomes a pretty daunting task!

For someone like me, who has a lot of stuff but also is comfortable with and enjoys making different outfits, the aspect of choice is nice. But I get that most people aren’t internet clothing weirdos like me.

A good way to begin feeling comfortable with clothes, without getting overwhelmed with choice, is to start out slow with a handful of pieces you really like. Pieces that make you feel confident and handsome. Pieces that fit with your job and lifestyle.

Maybe it’s khaki pants, an oxford shirt, and a v-neck sweater. Maybe it’s a pair of well-fitting jeans, sturdy boots, and flannel shirt. Start there and then branch out a little when you’re ready.

Being stylish doesn’t mean “having a lot of clothes to choose from” or “wearing something different every day”. I’ve written before about how I love simplicity in clothing. I have also written about how I don’t really buy into the view that one needs to be “creative” in order to be stylish.

If you find yourself getting a little agita at the prospect of getting dressed for work or dinner or an event, it might mean you’re dealing with a bit too much choice. Pare down your options if needed until you feel like you’re in a space where the choice is fun instead of daunting.