Op-Ed: 5 Types of Jeans and When You Should Wear Them

Blue jeans are an essential part of any guy’s closet, and have likely been a feature in your own for as long as you can remember. But how well do you actually know your jeans? Odds are, probably not as well as you think, at least not when it comes to their specific style.

So, allow me to provide you with a little refresher. Below, I’m going to discuss all the major jean cuts, detailing when to wear them, what to wear with them, and who should avoid them at all costs.

skinny jeans


The Skinny Jean gets a bad rap, and it’s easy to see why: the hip-hugging fit isn’t going to be to everyone’s taste, and can be downright uncomfortable for some folks. However, this doesn’t mean you should shy away from skinnies altogether. When worn correctly — and in the right setting — this style of jean can be super becoming, and can actually elevate what would otherwise be a basic denim look into something fashion-forward. Plus, the cut shows off leg day gains in a cheeky way that could be fun for folks putting in those reps.

  • When to wear: Smart casual cocktail parties, art gallery openings, basically any event in which you need to stand (and look good!) for long stretches of time.
  • Wear with: Loose button-down tops, crisp T-shirts, fitted blazers, sleek leather boots.
  • Pitfalls: The major pitfall here is mobility, so if you’re going to an event that requires you to move a lot, I’d avoid.

slim jeans


If Goldilocks were to choose a style of jean, it would be the Slim cut.

Featuring a tapered cuff in the spirit of Skinny Jeans with the more relaxed waist of a Straight-leg jean, Slim denim pants look good on almost everyone and can transition from casual to dressy with ease. Though I wouldn’t necessarily recommend them for physical labor or intense outdoor play, they could make a great go-to for guys who want a relaxed fit, but also something that’ll show off the assets.

  • When to wear: Date night, dance parties, formal brunches, basically any “nice” event that’ll require a lot of moving around or shifting from standing to sitting. Also totally appropriate for a professional setting.
  • Wear with Truly, anything! T-shirts with a crisp french tuck or a relaxed fit button-down are always solid options.
  • Pitfalls: As with skinny jeans, there’s a slight mobility issue, but most folks should be okay. If you’re particularly muscular or more heavy set, you may want to consider one of the following styles.

straight jeans


As the name suggests, Straight cut jeans are straight from waist to cuff, creating a streamlined silhouette with very little hug. This is the most popular jean style, as it lends itself well to a variety of different body types and shapes. However, this comfort does mean the overall effect can be a tad lifeless, as it basically makes two denim cylinders of the legs. To edge up the look, keep an eye out for distressed jeans that feature stylish rips and tears.

  • When to wear: BBQs, outdoor adventures, basically any outing in which you’ll be around folks, but the emphasis is more on comfort than style.
  • Wear with: Keep the tops as casual as the bottoms and you’ll be good to go. Think button-downs, vintage T-shirts, and sweaters.
  • Pitfalls: Can make some guys look “boxy,” so try to opt for jeans that have a bit more shape at the waist.

bootcut jeans


Originally designed for cowboys (seriously!) the Boot Cut Jean flares slightly at the ankle in order to accommodate, well… boots. The cut isn’t so popular anymore, but does make for an excellent utilitarian option when you’ve gotta wear jeans for actual work. And though your projects probably aren’t of the steer-wrangling variety, I’d highly recommend whipping on these bad boys when doing household chores or gardening.

  • When to wear: Yard work, rodeos, basically any situation in which you need to be moving outdoors.
  • Wear with: Relaxed flannels, denim button-downs, worn-in boots, anything that’s rugged and a little roomy.
  • Pitfalls: Not the most flattering look on shorter guys, but works well if you’re loaded down with gear or need to wear a pair of bulky boots. They can also look a bit like flares, which is fine if you dig a retro style, but may be a dealbreaker if you don’t.

relaxed fit jeans

[Levi’s 550 Relaxed Fit Jeans]


Sold on the loose cut of the Bootcut, but want something a little more stylish? They you may want to consider the Relaxed Jean, a comfortable cut that looks as good as it feels. Thanks in part to the 90s nostalgia swirling in fashion circles these days, relaxed pants are having a moment, which could spell good things for guys who need a little wiggle room in their jeans. Pro tip: Look for relaxed jeans with a tapered cuff as this may be an ideal way to pull off a modern look if you’ve got larger thighs.

  • When to wear: Park outings, BBQs, basically any day outing in which you want to look good, but comfortable.
  • Wear with: Sweaters, T-shirts, flannels tied about the waist.
  • Pitfalls: Slim or naturally thin guys may want to avoid the relaxed look, but muscular or heavier set folks could find a lot to love in the roomy cut.

Well folks, that about does it for this denim rundown. If you have any questions, or want some more tips for snagging the perfect pair of jeans, leave a comment below!

Editor’s note: This article is an op-ed. The views expressed herein and in the video are the author’s and don’t necessarily reflect the views of Stridewise, LLC. Claims, assertions, opinions, and quotes have been sourced exclusively by the author.

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Cody Gohl is a New York-based writer with extensive experience covering men's fashion and health and wellness.

3 thoughts on “Op-Ed: 5 Types of Jeans and When You Should Wear Them”

  1. Yoo-hoo! Hey, guess what? I think this article would be very useful for my sister-in-law to help her make the right purchase anytime soon. I didn’t even realize that slim denim jeans are totally acceptable in formal environments too, provided we complement it with a suitable top. Recently, she just got a new job at a travel agency near her house and the place has a very casual dress code.


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