How to Style Levi 505s (Relaxed Fit Pants)

Watch the Video Here**

Alright, just don't overthink it.

Levi's 550s are a casual, relaxed-fit pair of denim. They're literally as classic as they come.

These aren't Levi's 550s, but they're a similar fit. So I'm gonna kinda show you what I mean with these.

You're trying something new, and the first thought is, I need to change everything that I normally wear to fit this style. I get it, it's completely normal, I did the same thing. I'm just asking you, with these, just think of them as a very natural starting point.

I get that they're relaxed fit, but they're not baggy. They're not what you think. If you're like me and you're used to the slim fit, this may feel like it's completely different.

Whether you like slim, straight, or relaxed fit jeans, they're really all the same thing. It's just a really standard fit. They're not skinny and they're not overly baggy. It's just a classic silhouette. For that reason they don't require that much creativity.

When I first got these, I thought I needed to wear them with like a bulky tennis shoe like this.

And these look fine.

But what if you go really bulky with like something like these Eddie Bauer hiking boots?

And they're still fine.

So then you think I definitely can't wear them with a slimmer tennis shoe like this,

but they still look fine.

The silhouette is classic, so they go with just about anything.

Now as far as the rest of your outfit, I tend to think that with such a classic silhouette, the rest of your outfit should be classic also, and by that I just mean really easy and effortless. I really don't think you need to try too hard with this.

Like if I just throw on a button up,

this is something I would wear all the time and it's just really easy, just throw it on.

Crewneck sweatshirt,

relaxed, easy.

I mean if you want to go with a boxier t-shirt,

you can do that

or even just a classic menswear fit.

Now I'm probably not going to wear an oversized Kyle Kuzma pre-game sweater or a skin tight t-shirt because that's just not the vibe of these jeans. I'm not saying you can't do that, I'm just saying I wouldn't.

All of those shoes and all these shirts are well within my normal style. And that is something that I love so much about this kind of style denim.

Switching from a slim fit to these was actually a lot easier than I anticipated. You just have to get used to how the denim sits on your shoes because that took me a while.

I mean and from here, I throw on a jacket, put on some jewelry, put on a hat.

I mean it's really that simple.

You may not go out and get a bunch of compliments on this outfit, but it is effortless, it's easy, and I feel good wearing it, which is why I love this kind of style. Just don't overthink it. Classic silhouettes call for classic style, and to me, that just means nice and easy.

Hope this helps.