Vintage-Inspired Casual Style That Feels Right Now · Primer

An easygoing mix of broken-in essentials that feels familiar, rugged, and effortlessly put together.

A denim shirt over a t-shirt, jeans, and sneakers isn’t a complicated formula, but the way these elements come together determines how and where the outfit fits into your life. 

On the surface, it’s simple, but the specific choices in fit, color, and material push it in a certain direction. The result is a look that’s casual but cohesive, easy to wear without feeling basic.

Last year, we featured a similar outfit, following the same framework but landing quite differently: a dark denim shirt, gray chinos, and chunky dark gray suede boots meant for a casual office. Same basic concept, but the effect noticeably shifts. 

One leaned toward a polished casual office vibe, while this version is more relaxed, rugged, and even has a touch of vintage inspiration in the brown jeans and canvas high-tops, calling back to classic style cues from the ‘70s and ‘80s, but in a way that feels modern rather than like a costume.

The choices in fabric, color, and footwear might seem subtle, but they completely change how and where you’d wear each version.

The Denim Shirt: An Open Layer That Sets the Tone

Denim shirts sit in a space between a jacket and a button-up, making them a solid option when you want something structured but not stiff. Here, it’s worn open over a pocket t-shirt, which keeps the outfit relaxed.

The small changes in denim tone and details matter. A darker, crisper denim shirt works when you want a cleaner, slightly more polished look. A more washed-in, broken-in denim shirt leans into casual ease. 

Both work—the question is what effect you want. And in a men’s personal style rooted in enduring basics and subdued colors this question is the primary driver in figuring out what to wear.

The Brown Jeans: A Small Shift That Changes the Feel

Brown jeans stand out but they’re not loud. They work like blue denim but bring in warmth, which subtly changes the outfit’s overall tone. This creates a contrast with the cooler tone of the denim shirt, making the outfit feel a little more natural and laid-back.

The previous outfit used gray chinos, which kept everything neutral and structured. Gray works well when you don’t want your pants to be the focus, allowing the denim shirt to take center stage. Brown, on the other hand, adds depth and holds its own against the denim shirt as an eye focus.

Beyond just color, these pants change where you’d wear this outfit. The previous version with chinos and suede boots was a great option for a casual office setting—polished enough to look intentional, but not too formal. The brown jeans and sneakers in this outfit push it further into the realm of off-duty wear—something comfortable, practical, and relaxed. 

It’s still put-together, but it’s meant for weekends, coffee runs, and everyday errands rather than a professional setting.

Neither choice is better, just different.

For someone who typically defaults to blue jeans, brown is an easy way to add variety without stepping too far outside the comfort zone.

The Sneakers: What Grounds the Outfit

The off-white Converse 70s play a key role here. The warm, neutral color keeps the outfit balanced by playing on a lighter tone of the jeans. The enduring nature of a simple, minimalist canvas high top contributes to the overall style in a way a modern athletic sneaker never could.

Previously, the dark gray suede boots made a big difference in the lower half of the outfit. Boots automatically add weight and a more grounded presence, which worked well with the dark denim shirt and gray chinos. Canvas sneakers, on the other hand, keep the whole outfit light and relaxed.

If you liked the look of the previous outfit but want something a little more laid-back, swapping boots for sneakers immediately shifts the feel.

The T-Shirt: A Base That Doesn’t Compete

A solid, dark t-shirt holds the look together without drawing attention. It creates just enough contrast with the denim shirt, preventing the outfit from looking flat and departs from the tan-hued jeans and sneakers. This could easily be swapped for a graphic tee, which would shift the focus, or a lighter neutral like heather gray, which would brighten the contrast.

The main takeaway? If you want to keep an outfit looking effortless, a dark solid tee is an easy choice. If you want more personality for this outfit, the t-shirt is the easiest place to experiment.