Walk into any bar in Manhattan or a boardroom in Chicago and you’ll see the same thing. Sea of blue. Wave of white. It’s the uniform of the modern world. But here’s the thing: most of those guys look like they’re wearing their dad’s hand-me-downs or a stiff cardboard box. They don't understand that button up shirt styles aren't just about "looking professional." It’s actually about architecture for your torso. Honestly, if you get the collar wrong or pick the wrong fabric weight, you might as well be wearing a trash bag with buttons.
Choosing a shirt is a tactical decision. You’ve got to consider the weave, the spread of the collar, and whether that hem is meant to be tucked or left flapping in the wind. Most guys just grab whatever is on the rack at J.Crew and call it a day. That’s a mistake. A big one.
The Great Confusion: Button-Down vs. Button Up Shirt Styles
Let's clear this up immediately because it drives tailors crazy. Every button-down is a button up, but not every button up is a button-down. It's simple geometry. A "button-down" refers specifically to those tiny buttons on the tips of the collar that fasten it to the shirt body. It was originally a sport thing—polo players in the late 19th century didn't want their collars flapping in their faces while galloping. John Brooks (of Brooks Brothers fame) saw this in England, brought it to the US in 1896, and the "OCBD" (Oxford Cloth Button Down) was born.
If those collar buttons aren't there? It’s just a button up shirt. Or a dress shirt. Or a sport shirt.
Why does this matter? Because a button-down collar is inherently casual. Wearing one with a formal tuxedo is a cardinal sin in some circles. It’s like wearing hiking boots with a three-piece suit. It creates a visual clash that most people can't quite name, but they know something looks "off." You want a crisp, stiff collar for formal events. No buttons. Just internal stays—those little plastic or metal tabs—to keep things sharp.
The Oxford (OCBD) Is Your Best Friend
If you only own one type of shirt, make it a heavy-duty Oxford. The weave is a "basketweave," where multiple weft threads are crossed over an equal number of warp threads. It’s chunky. It’s durable. It breathes well but has enough weight to hide your undershirt. Brands like Drake's or Wythe have perfected this look lately, leaning into a slightly "shaggier" texture that looks better the more you wash it.
You can wear a white Oxford with a navy blazer. You can wear a striped one with beat-up chinos. You can even wear one over a t-shirt like a light jacket. It’s the Swiss Army knife of button up shirt styles. Just don't try to wear it to a black-tie wedding. The texture is too rugged; it’ll look like you’re wearing a canvas tent compared to the groom’s fine poplin.
Let’s Talk About Weaves Because They Change Everything
Most people buy shirts based on color. That’s amateur hour. You should buy based on the weave. The way the fabric is constructed dictates how it drapes, how much it wrinkles, and how hot you’re going to get during that 2:00 PM presentation.
Poplin is the standard "dress shirt" fabric. It’s a plain weave, meaning it’s smooth and thin. It looks very sharp when ironed, but look at it the wrong way and it wrinkles. If you’re traveling, poplin is your enemy. You’ll step off the plane looking like a crumpled piece of loose-leaf paper.
Twills are different. You can spot a twill by the diagonal ribbing in the fabric. Think of denim—that’s a type of twill. In button up shirt styles, a fine "royal twill" has a bit of a sheen and resists wrinkles much better than poplin. It’s heavier. It feels "expensive." If you want to look like the boss, buy twill.
Then there’s Broadcloth. It’s basically Poplin’s denser cousin. Very formal. Very traditional.
- Flannel: Not just for lumberjacks. A brushed cotton flannel is the ultimate winter button up. It traps heat. It feels like a hug.
- Linen: The summer king. It’s made from flax fibers. It wrinkles instantly, but that’s the point. It shows you’re relaxed. If you’re at a beach wedding, linen is the only correct answer.
- Chambray: Looks like denim but it’s a plain weave. It’s a workwear staple. It says, "I might be an architect, or I might be able to fix your sink."
The Collar Is the Frame for Your Face
The collar is the most important part of the shirt. Period. It frames your face and can either balance out your features or make you look like a bobblehead.
If you have a narrow, thin face, you want a spread collar. The points are wider apart. This adds visual width to your head. If you have a rounder, wider face, you want a point collar. The points are closer together, creating a vertical line that elongates your neck and face.
The "Mid-Spread" is the safest bet for 90% of men. It works with or without a tie. It’s the "Goldilocks" of button up shirt styles.
Lately, we’ve seen a massive resurgence of the Camp Collar. This is that flat, notch-lapel style collar you see on Hawaiian shirts or "bowling" shirts. It’s meant to be worn open. No tie. Ever. It’s the ultimate vacation shirt. Brands like Todd Snyder and Percival have made these cool again by using high-end fabrics like Tencel or silk blends instead of cheap polyester.
🔗 Read more: Why Mens Medium Weight Jackets Are Actually The Only Outerwear You Need
Fit Is Where It All Goes Wrong
You can spend $500 on a hand-sewn Italian shirt, but if the shoulder seams are hanging two inches down your arm, you look like a clown.
"Slim fit" is a trap for some. "Classic fit" is a tent for others. The truth is usually in the "Contemporary" or "Athletic" fit. You want the shoulder seam to sit exactly where your arm meets your torso. Not before, not after.
The sleeves should end right at the base of your thumb. When you wear a suit jacket, about half an inch of shirt cuff should peek out. This isn't just an old-school rule; it’s a functional one. The shirt cuff protects the expensive wool of your jacket from the oils and dirt on your skin.
Also, please check the length. If the shirt has a curved "tail" (a "scoop" at the bottom), it’s meant to be tucked in. If the bottom is straight across, it’s meant to be worn untucked. Wearing a long-tailed dress shirt untucked makes you look like you’re wearing a nightgown. Stop doing it.
Real-World Examples: Who Is Doing It Right?
Look at someone like Jeremy Strong or Jeff Goldblum. They understand the nuance of button up shirt styles. Goldblum often leans into the "Grandad collar" (also known as a band collar). It has no collar leaf at all—just a band of fabric. It’s modern. It’s edgy. It says you know the rules well enough to break them.
On the flip side, the "Power Shirt" of the 1980s—think Gordon Gekko with the contrasting white collar and blue body—is making a niche comeback. It’s a bold move. It’s aggressive. It’s definitely not for the faint of heart or the entry-level intern.
The Rise of the "Shacket" or Over-shirt
We can’t talk about shirt styles without mentioning the hybrid. The over-shirt is a button up made of heavy wool, corduroy, or moleskin. It’s cut slightly larger so it can fit over a sweater or a tee. In the "lifestyle" category of fashion, this is currently the MVP. It bridges the gap between a jacket and a shirt. It’s perfect for those weird spring and autumn days where the weather can't make up its mind.
Actionable Steps to Fix Your Closet
Don't go out and buy ten new shirts today. That's a waste of money. Instead, do a quick audit of what you have and fill the gaps.
- Identify your "Core Four": You need one crisp white Poplin (for weddings/interviews), one light blue Oxford (for daily wear), one Navy Chambray (for weekends), and one Flannel or Linen depending on your climate.
- Check the Collars: Throw away any shirt where the collar has "collapsed" or lost its shape. A limp collar makes you look tired and unprofessional.
- Visit a Tailor: Most guys don't realize that for $15–$20, a tailor can add "darts" to the back of a baggy shirt to make it fit perfectly. It’s the cheapest way to look like a million bucks.
- Feel the Fabric: Stop buying 100% synthetic shirts. They don't breathe. They trap sweat. Look for "100% Cotton" or "Linen-Cotton blends." Your skin will thank you.
- Learn the Iron: Or get a steamer. A wrinkled shirt is a sign of a cluttered mind. If you're going to wear a button up, own the maintenance that comes with it.
The reality is that button up shirt styles are a language. You’re telling the world how much you care about the details. Whether you're going for the rugged workwear vibe of a Filson scout shirt or the sharp, minimalist lines of a Theory dress shirt, make sure the "language" you’re speaking matches the room you’re standing in. Most people won't notice your shirt if it fits perfectly—they'll just notice that you look "good." And that's exactly the point.