The “Break It In” Lie

When you’re just starting out in menswear, or even if you’re an old hand, you might not know how some things are supposed to fit or feel.

A pair of well-made shoes at a higher price point are going to feel different than the squishy glued versions from DSW.

A proper brimmed fur felt hat is going to feel different than a baseball cap.

This is all normal. And if you’re in a shop struggling with whether or not you think something fits you, I hope you are aided by a patient and knowledgeable salesperson (like the incredible staff at JJ Hat Center in NYC who warmly guided me through my first hat-buying experience many years ago).

Unfortunately, there are times when a salesperson (often well-meaning, but sometimes not), or total randos on the internet, will spout an infamous line that has led to many wasted dollars and hours.

“Break it in.”

“Just give it a little time to break in and it will be fine”, they’ll crow. That tightness, or pinching, or slippage, or rubbing, or digging, will all go away once you “break it in”.

They’ll make it sound like there will be a magic moment when those uncomfortable shoes will miraculously feel like butter.

You also might feel as if you have to “earn” that comfort by breaking it in. As if the pain or discomfort is some sort of entry fee into an exclusive club of well-dressed, richly patina-ed gentlemen.

This is all nonsense. There are times when it makes sense to give an item a little bit of time to soften up before you can fully enjoy it. But that discomfort should be nothing more than a twinge to start with. Something that your mind can ignore after a couple minutes of wearing so that you can wear the thing over and over again without wanting to stab yourself in the eye.

I’ve written before about my Red Wing Iron Ranger boots I bought over a decade ago. When I purchased them they were by far the highest quality item I ever owned. I also knew that they were going to need a little breaking in before they were totally comfortable. Turns out they were never totally comfortable but it wasn’t because they didn’t break in sufficiently (they just weren’t the right boots for my particular foot).

The ”break in” process for those boots was actually kind of fine. Red Wings are notorious for having a terrible break in period but I didn’t feel that way with my boots. Yeah, they were stiff, but they’re leather and leather needs a little time to soften. I’ve owned enough baseball gloves in my life to know that.

My boots rubbed a little bit in the heel and at the top of the boot around my ankle. But I wouldn’t say anything was painful. Just a little stiff. And after I wore them a handful of times it was totally fine. I’d say probably a week of daily wear made them perfectly serviceable.

Not a big deal. That’s an example of an acceptable break in period.

Here are two examples of UNacceptable break in periods…

About two years ago I bought a pair of raw denim jeans. I’ve never been a “denim head” because I think jeans are disposable, casual work clothes, but these jeans were on a crazy discount so I pulled the trigger.

I had read all about how raw denim kind of sucks to wear at the start but then they soften up and become amazingly comfortable as they mold to your shape.

Well, two years in and whenever I wear them I want to rip them off and chuck them out the window. I’ve worn them a lot and they are not getting any softer. They are just as stiff and uncomfortable as they were when I bought them. I’ll wear them for a few days and think “maybe this isn’t so bad”, but then I switch over to a normal pair of pants and think “Wow, this is so much better. What was I thinking?”

At another point maybe five years ago or so, I pulled the trigger on a felt hat from a new hatmaker. It was a small company and I love hats so it felt good to throw some business their way.

The hat looked great in the pictures on the website. Kind of a blend between a city and country style the way the old Stetson Open Roads used to be. When the hat arrived though, I could tell this was more of an Instagram prop than an actual hat.

The thing was cardboard stiff and wore like I put a plastic tub on my head. I reached out to the company regarding a return label and the owner asked me why I was returning the item. I believe he genuinely wanted honest customer feedback. I told him about the stiffness and how the hat was uncomfortable. It was then he told me I just needed to break it in. And once I did that it would be fine.

No, thank you. I can buy a Stetson or Akubra for the same price and have something comfortable from day one.

My big question for everyone who says “break it in” is: Who has TIME for all of this?

When I buy my clothes, I want them to be comfortable from the start. That’s a normal expectation. If there is a little tickle here or there that will smooth out in the course of a few wears, fine. But I’m not spending years or even months doggedly wearing items that cause me grief hoping to attain some sort of elusive sartorial nirvana once things finally “break in”.

The bottom line is this: If you try something on and it doesn’t feel right then it isn’t right and you should move on. Don’t let a salesman, or your own mind, gaslight you into believing it will all be fine once you break it in. You’ll be throwing away money and time and as dads, we don’t have an unlimited supply of either.

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