What to Wear With Relaxed Fit Jeans

by Jamie Wilson
What to Wear With Relaxed Fit Jeans

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

Relaxed fit jeans are to ultimate in men’s casual and comfortable clothing and this style guide will show you how to style them this season.

What to Wear With Relaxed Fit Jeans
@Jayson Hinrichsen via Unsplash

Jeans shopping can go one of two ways; it can be a happy time or a not so happy time if the ones you want don’t fit right. It is never easy and can be pretty time consuming. If you get the wrong fit, your outfit just ends up looking below par. With all the different cuts and shapes it’s hard to know what to wear with a specific style, so we’ve got it covered.

Relaxed fit jeans are the roomiest of all the jeans with a fuller leg and seat (hence the name). Just be careful not to wear them too ‘saggy’, you don’t want to end up looking like a throwback to a cheesey 90’s boy band.

What to Wear With Relaxed Fit Jeans
@Masood Aslami via pexels

The Jeans

Edwin has a great pair of relaxed tapered fit jeans, with a classic mid-rise style they are great to keep for years. They’re a very casual fit so it’s best not to try and dress them up. Keep them solely for your casual days or, if your office dress code is pretty casual, you can probably get away with them if you have the right styling up top.

What to Wear With Relaxed Fit Jeans
@Kamil Rybarski via pexels

Styling Your Jeans

Relaxed fit jeans look great with most T-shirts, just make sure the style isn’t long in the body, as the jeans are loose fitting, a long line T-shirt will just make you look bigger. If you want to go for a more printed look then this tee by Y.O. is a big contender. Minimal print but the right impact.

If print isn’t your thing then go for a plainer option, the choice of sleeve length is yours, but for this coming season I’d suggest a long sleeved version to give you that little bit extra warmth.

Styling Your Jeans
@David Gomes via pexels

The Jacket

With loose fitting clothing, the general rule is – don’t wear relaxed fit trousers with a baggier top and jacket and vise versa. You might just end up looking like you’ve got dressed in the dark or like Kevin Federline back when he was with Britney, and no one wants to look like that!

So for the jacket, again stay clear of something long in the body like a parka, or anything oversized like a padded jacket (these look great with skinny fit, or slim fit jeans), go for something like a light bomber. For the winter months the leather flight jacket by Levi’s will look great with the jeans and will keep you warm.

The Jacket
@Marty O’Neill via Unsplash

To Cuff or Not to Cuff?

Cuffing jeans has come back into fashion; it’s more of an American work wear style that has now become acceptable in everyday wear. Cuffed jeans are different from rolled jeans, you usually just roll them once and they should stay the exact width of the leg, unlike rolling where you generally want them to be higher up the leg and a tighter fit at the bottom.

Cuff jeans look great with a less chunky shoe like a Superga or Converse plimsoll or for a smarter shoe a pair of desert boots which will sharpen up the look. Try and stay clear of any chunky boots with this fit as it can look too bulky.

Feature image from Pexels

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