Casual Style: Mixing Tailored Pants and Tees

An effortless(?) mix of casual and dressy.

I’ve always enjoyed the idea of tailored pants with t-shirts. There’s something about it that balances on the fine line between dressy and dressed down that appeals to me. It’s a great relaxed look for summer.

Having tried it and missed the mark previously (no I’m not sharing photos…), but still finding the concept appealing I decided recently to give it another go.

I’ll share what makes it work in my opinion, and what can make it not work. A couple of examples of other people nailing it – both vintage and recent – will be included too for a primer on how to rock it.

Let’s jump in!

People Who Nailed It

A Classic Example:

For a vintage example we look no further than star actor Marlon Brando in the film ‘A Streetcar Called Desire’ (1951).

This photo exemplifies the louche appeal of the tee and tailored pants look. It also busts the myth that you can’t wear sneakers with an ensemble like this, though tread carefully if trying it; stick to plainer, cleaner trainers like Adidas’ Stan Smith model or a plimsoll style shoe.

A Contemporary Example:

For this one, I’m going to reference the man who I think is the king of the tailored pants and tee look on Instagram: Zane Lim (@thezanification).

There are a few recognisable details in both Marlon’s and Zane’s looks that showcase how you too can pull off this look. Let’s delve right in…

What I Think Makes It Work

There are two key components to get right; the first is the fit of the tee. You want to make sure it’s fitted, as a loose or oversized tee will just look sloppy. As such, you’ll find this look works better for you if you have a toned physical shape to your upper body.

The second concern is the trousers in general; fabric and fit.

It’s important to select a fabric that will look good in a more casual setting. This means you should avoid a super formal fabric like worsted wool. If you’re trying this look in summer, something like linen would be a perfect selection. You could also go for a seersucker, lightweight cotton or even a summer weight wool like fresco. The summer trouser fabric article on Permanent Style is a good source of further reading on this topic.

Lastly, consider the fit and details of the trousers. In my experience the look seems to work best with high rise trousers such as Zane’s pictured above, but natural rise trousers should work fine also. You’ll want to avoid tightly fitting trousers as you want to showcase some drape.

Given the simplicity of the tailored pants and tee look, having some standout details on your trousers is a good idea. Pleats, small flap pockets and other sartorial flourishes get a chance to really shine in these looks.

My Most Recent Tailored Pants and Tee Look:

I paired a Uniqlo U tee in orange with some high waisted navy blue Brooks Brothers linen trousers. I added a small necklace for some extra detail on the top half and let the details of the trousers speak for themselves.

How Not To Do It

In my experiments with this look, here are some things I’ve found to make it a miss (or potential miss).

Definite Miss

  • Wearing worsted wool trousers. They’re too far on the formal side of the scale.
  • Using a baggy tee.
  • Wearing the tee untucked.

Possible Miss

  • Wearing a graphic tee*. This will limit your options for trouser fabrics that work with the look to only the most casual.
  • Attempting the look with low rise trousers. Unless a low rise is definitely what you need, stick with a regular or high rise.

*This isn’t to say you can’t do it. I recently did it with a graphic tee and some flat front seersucker pants with a casual belt. I liked it, but I’ll let you decide if it’s a look that works for you:


Pairing a tee with some tailored pants is a great way to show some sartorial flair on ultra casual days. With the heat we’ve recently been having in Australia, I’m sure to be rocking a few more of these looks.

And, as far as I’ve defined some components within this look that don’t work for me, that doesn’t mean you shouldn’t try it for yourself if you want to. After all, your style is yours.

What’s your favourite casual tailoring look?

Continue reading…

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With content features ranging from appearances on popular menswear hubs (The Rake, StyleForum, Put This On) to French perfume newsletters and university course readings, Sam is a writer, designer and enthusiast in the fields of menswear and fragrance.

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