There’s No Shame in Being a Jeans & T-Shirt Guy: Here’s How to Do It Intentionally

For rebels with or without a cause, this isn’t just a look. It’s a way of life.

Sloppy. Childish. Underdressed. Slovenly. Those are just a few of the terms we’ve heard to describe how it looks to wear jeans and a t-shirt for all but the most casual occasions.

A lot of entry-level fashion advice shuns t-shirts and jeans. Nothing says, “poorly dressed” more, you'll read. And a lot of this advice makes men over-correct: Believing they have to wear suits everywhere they go.

This advice is well-meaning, but it's missing the point. Yes, many men who rely on t-shirts and jeans ARE poorly dressed. But it's not because they're wearing t-shirts and jeans. It's because they're not dressing intentionally.

Everyone’s favorite casual outfit is simple in theory, but difficult in execution. By paying attention to details like material, fit, and color (or rinse), you can make this minimalist outfit not a cop-out, but both stylish and intentional.

Basic is anything but boring.

Let’s break it down.

how to dress well with t-shirt and jeans

bootsgap henleygap henleyamazon bomberquilted bomberquilted bomberamazon henleylevi's 511Orientbest affordable dive watches

The Shirt

Henley: Gap, $15 / Alt: Amazon, $20

T-shirts are one of the most commonly made menswear items in the world, with a great history going back to the Spanish-American War. You can buy them in a 3-pack in the corner store. You can buy a $500 designer version, if you so desire. Whatever you choose, go for one that looks like that choice was conscious. Save your old, stretched-out tees with the strategic air conditioning (read: holes) for gym days and beach trips. In order to pull off a t-shirt, you want one that reads relaxed, yet with a hint of polish. This also means most shirts with quirky phrases and/or large illustrations are best saved for very casual occasions.

Here, we’ve swapped the garden variety long sleeve graphic t-shirt for a charcoal henley. The button placket and texture are details that draw the eye and add visual interest, which is important when you’re mixing basic pieces in neutral hues.

But more importantly, it fits. It's slim to the body, which is not the same thing as wearing a tight t-shirt. This means that there shouldn't be a ton of extra width and length. Official nationwide Primer studies performed by the finest universities confirm that 98.384% of men wear their t-shirts at least one full size too large. By wearing a t-shirt that actually fits, you automatically enter the 1% of better dressed men.

capitol records building bomber jacket henley gray jeans boots

Bomber (similar): Nordstrom, $105 / Alt: Amazon, $39
Henley: Gap, $15 / Alt: Amazon, $20
Slim Stretch Gray Denim: Levi's 511 in Chainlink color, $48
Gray boots: Amazon, $120

Read more: How Everyday Clothing Was Influenced by Military Style: A Visual Timeline

The Jeans

Slim Stretch Gray Denim: Levi's 511 in Chainlink color, $48

Although dark blue will always be a good choice, jeans are available in any number of colors and rinses. Try a slightly more faded style, or a gray or black wash denim. You’ll feel like you’re breaking out of your style rut, and there’s something about a pair of non-blue jeans that reads as more polished and purposeful.

man tshirt gray jeans quilted bomber

The fewer pieces your outfit has, the more work each piece has to do. So make sure your jeans are doing their share of the heavy lifting. Here, this lighter pair balances out the darker shirt and jacket. You can also try a lighter tee with a darker denim rinse. There’s nothing wrong with a monochromatic outfit, but the contrast adds an obvious intention to an otherwise simple uniform.

Read more: The Essentials: Gray Denim – 6 Complete Outfits That Prove It Will Change Your Wardrobe + 50 Image Inspiration Album

navy quilted bomber jacket

The Jacket

Bomber (similar): Nordstrom, $105 / Alt: Amazon, $39

There are a number of jackets that look great when paired with jeans and a t-shirt. A trucker jacket or leather jacket is classic, and some guys can pull off the denim-on-denim look of a Texas (or Canadian) tuxedo. But we like to mix it up just a bit with a bomber jacket. The lightweight shape of the jacket is still casual, so it doesn’t conflict with the other items, but the quilted texture makes it clear that you picked this piece on purpose. If you're shopping around for one, be mindful that many quilted jackets are for colder weather; so if you plan to wear it for spring, you'll want to ensure it's a lighter version.

Read more: 25 Spring Jackets for Every Personal Style

men casual style

Last But Not Least: The Goldilocks Rule

When you’re getting dressed, follow The Goldilocks Rule — not too big, not too small. Just right. If fit is important when choosing your collared shirts and dress pants, it’s important when it comes to your casual clothes, too. The best-fitting t-shirts and jeans will be neither too baggy nor too tight, but will skim your torso and limbs in a flattering way without being constricting.  Look for cuts that follow the shape of your body: a boxy tee automatically looks haphazard, as do jeans with several extra inches of material pooling around your ankles.

Jumping off point: How an Untucked Casual Shirt Should Fit – A Visual Guide

Get the Look

Bomber (similar): Nordstrom, $105 / Alt: Amazon, $39

Henley: Gap, $15 / Alt: Amazon, $20

Slim Stretch Gray Denim: Levi's 511 in Chainlink color, $48

Gray boots: Amazon, $120

If you like the minimalism of this outfit, you'll love Minimalist Style: Dress Better With Less Effort + 5 Complete Getups For Inspiration!

Like this post? Please share it!

Ali grew up in New York and currently lives in Philadelphia, where she works as a copywriter. She enjoys cooking, playing the guitar, and powerlifting, and has a brown belt in Krav Maga. You can find her collected articles on health, fitness, and other lifestyle topics at https://alibzagat.contently.com/ Instagram: @alibzagat

2 Comments

  • Reply April 25, 2019

    Joseph

    As my wife (and female colleagues) would say, “T-Shirts are fine – as long as they fit well and don’t have a lot of writing on them.”

    Somehow the old “Eat The Worm” Tequila t-shirt and ratty oversized “Bud’s Bait-N-Tackle” t-shirts didn’t make the cut.

  • Reply April 26, 2019

    Zac Silk

    Still got this exact bomber it’s a great investment. Lucky for me my work is relatively causal, and I can get away with jeans and a t shirt most days.

    Normally I default to something similar to this getup. A slim pair of jeans a well fitting crew neck t shirt and some desert boots.

    It’s definitely a good comfortable getup to go back to again and again.

Leave a Reply