The Upgrade Shirt — Bruce Layman

If you’re looking to make some style changes or start “dressing better” (an idea worth unpacking in its own right) it can be daunting to figure out where to start. This is the first in a series I’m calling The Upgrade. Each article will focus on one area of your closet. The goal is to pick one piece you work in, wear out, and use to refine your personal style.

The first piece we will tackle is one that will likely get the most wear: The Shirt.

Well, more specifically the dress shirt. I’ll cover to t-shirts and polos some other time.

Right now you probably have at least a few “dress shirts” in your closet.

There’s that shirt that came with the suit you bought that you only wear once every two years. It’s white, has a spread, or maybe point, collar, and while it’s a decent shirt, it’s stuffy and you don’t want to wear that every week.

There’s probably a shirt or three that you wear but they fit you a little funny. Maybe they’re juuuuuust a bit big or small in the shoulders, or there’s too much room in the chest, or the sleeves do that weird balloon thing when you try to wear a jacket in the fall.

Maybe you’ve an Oxford cloth button down (OCBDs going forward) in blue—maybe pink?—kicking around from the menswear 2.0 days—save that, it’s a classic and will always be worth having.

Unless you’re a lifeguard, you’ve gotta wear a shirt every day. But, instead of adding a handful of shirts you might wear, or have to figure out how to wear, I’ve got a shirt that you’ll want to wear on Monday and wash so you can wear it Thursday, and maybe even toss it on casually on Saturday.

The Shirt

**I recommend a blue striped cotton *poplin* button down.**

This one from Drake’s might be my favorite.

This is an incredibly versatile shirt and that makes it valuable, and worth spending a bit more on. Maybe more than you’ve ever spent on a shirt before.

Let’s break this shirt down into its components.

The fabric: cotton poplin

Without getting into the intricacies of weaving, poplin is a plain weave fabric with a smoother, silkier surface and feel, while still being strong and crisp. It looks great pressed under a suit, but equally good a little rumpled at the hotel bar with jeans after a long day of travel. It’s a lighter weight fabric than Oxford so it wears cooler, and its smooth texture makes it a bit dressier—great for elevating an outfit, or providing a bit of contrast.

Though thin, the fabric is strong and you don’t have to dry clean it. You can wash it cold and hang dry it. I even throw my poplins in the dryer on air dry with my heartier oxfords in a pinch. They iron to a beautiful crisp, but if you don’t have the time, they will still look good with a few shakes in a steamy bathroom.

The pattern: a stripe

Preferably a bengal, or if you’re feeling particularly bold—maybe you should be—an awning stripe. At the very least, a university stripe (but you might already have this size in an OCBD, in which case, go for something a bit louder. A broader striped shirt lends some visual interest to a simple navy blazer sans tie, fall sweater, or winter jacket.

The difference in stripes is a matter of fractions of an inch—if you must know university stripes are roughly ⅛”, bengal ¼”, and awning ⅜” or wider—but it makes a difference as the bolder the stripe, the generally less versatile.

The color: blue

Even though you probably have a decent amount of blue in your closet already, I think it is worth adding one more. You can pick any blue you like, but keep in mind that a more intense blue will be a bolder statement, and potentially a bit less formal unless you’re used to making some more advanced moves (you can totally do this, I believe in you).

My recommendation is something in the sky blue or light blue family if you’re going for versatility.

The collar: button down

The final piece of the shirt is what makes it so special, and that is the collar. Normally, if you come across a blue striped poplin shirt, it’s spread collar, and while that’s a great shirt to have in your closet, I think going for a button down on a poplin shirt gives you the maximum wearability.

While not exactly a high/low combination, mixing the more formal poplin with the slightly less formal button down lets you wear perfectly no matter what the week brings.

Versatility equates to value

Put all these elements together and you end up with an incredibly versatile shirt. You can wear it to the office with trousers or chinos, or pair it nicely with jeans and a blazer for date night. And, assuming you didn’t sweat too much in it, you can roll up the sleeves and wear it a little wrinkly on the weekend.

This versatility makes this shirt a great value. I wore this shirt three times last week—yes I did wash it between wears one and two because it coincided with laundry day—but it’s also because I love this shirt, and I think you might too.

And I know what you’re thinking, “Bruce, you’re suggesting a nearly $300 shirt, you’re out of your goddamn mind.” And you might be right, but that’s a different thing entirely. Maybe you’ve never spent this much money on a shirt before. That’s okay. If it’s outside your budget, or you just don’t want to spend that much, there are other options. I didn’t pay full retail for mine either. I was very patient and managed to snag one on Grailed for a song.

A shirt like this is designed to flex across many of the sartorial situations you might find yourself in. It gets packed or worn almost any time I travel for work or pleasure, and I wear it no less than once a week. It’s worth paying a little extra for the best fabric you can get—and then being careful with your laundry, say it with me “hang dry”—to have a shirt that will last you for many years to come.

Now the part you’ve really been scrolling for:

What to buy

We will start at the high priced end of the recommendations with Drake’s. These are expensive, and if you go made to measure (something I highly encourage) they cost even more, but dammit if they’re not worth it. I love every Drake’s shirt in my closet. Their fabric and finishing touches are divine. [$275+]

Another great—and slightly less expensive—option, is made to measure from Sid Mashburn. I like the Blue Bold Awning Stripe, and you can definitely pull that off, I believe in you. If you can find one of their excellent stores or catch them on the road, they’ll measure you for a shirt and any time you want to add another one to your closet you can call or fill out the form online and have one shipped to you in a matter of weeks. [$200 ish]

In the $100-$200 range there are some great choices. Anglo-Italian has a beautiful shirt for $182, and Todd Snyder has one for $148. If you are feeling a bit more adventurous—and have someone who can help you take your measurements—you can build a Stanton 120s shirt from Proper Cloth.

And if budget is a concern, Land’s End has you covered at forty bucks. My first dress shirts were from Land’s End almost 15 years ago and I still have one or two of their oxford’s in my closet.