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Best untucked men's button-down shirts, according to style experts

Before your next Zoom call, consider trading in your favorite T-shirt for an equally comfy-yet-stylish men's button-down shirt. Here's how.
J.Crew; Peter Millar; Gap

With the line between working and working from home continuously blurring, untucked button-down shirts might be the new videoconferencing uniform. They’re comfortable and keep you from having to push shirt ends into your pants after reaching up or down, or otherwise stretching. And they achieve the traditional and professional look that’s become so typical of American working environments. Modern men’s shirts have been packing newer and ever more versatile materials, features and fabrics, giving you many options to consider and choices to make. For one, should you even consider going untucked with a button-down? One style expert certainly thinks so.

IN THIS ARTICLE How to shop for button-down shirts | Collars | Buttons and cuffs | Best button-down shirts

“Untucked is totally fine for work-related Zoom chats,” says Barron Cuadro, founding editor of Effortless Gent. “Nowadays, casual style is more and more acceptable. I think the problem arises when guys equate ‘casual’ with ‘sloppy.’ You can be dressed casually but still really sharp.” So how should you go about buying new button-down shirts? And what makes for the best button-down shirt to shop? Button-down shirts provide clues about when and how you’re supposed to wear them — you just have to know where to look. We consulted fashion experts and personal stylists about how to shop for button-downs and got their recommendations for shirts to match your style.

A good rule of thumb is that the hem of your shirt should hit right about halfway in the zipper of your pants. Nothing should completely cover the zipper or be too close to the button.

Will Noguchi, Visual Styling Manager, Bombfell

How to shop for button-down shirts

UNTUCKit boasts styles like the Wrinkle-Free Douro Shirt, which is designed to be worn untucked, but that’s not the case or norm for most button-down shirts on the market. Will Noguchi, the visual styling manager for Bombfell, a men’s clothing subscription service, has a quick test for whether or not a shirt has to be tucked in.

“A good rule of thumb is that the hem of your shirt should hit right about halfway in the zipper of your pants,” Noguchi says. “Nothing should completely cover the zipper or be too close to the button.”

Become a collar scholar

When it comes to picking a shirt, it’s best to start at the top. The collar is a good indicator of whether a shirt is formal or casual.

Spread collars, like that on the Proper Cloth Dress Shirt, give you a classic formal look, often paired with a wide tie. “If you have to dress up for a work video conference call, it doesn’t hurt to have a dress shirt on with a medium spread collar, even if you’re not tucking it in,” Cuadro says.

If you’re looking for a shirt that is a bit more casual, look to button-down collars. The shirt was popularized by Brooks Brothers, after John E. Brooks saw the style while watching an English polo match 1896. The original design, referred to as “polo,” turned the British uniform into a classic work shirt. “Long-sleeve shirts with button-down collars in a more Oxford type are good as an in-between,” Noguchi says.

When the Zoom conference call becomes a happy hour, that’s when you opt for a camp collar — the wide, distinct option that Vince Vaughn popularized in Swingers and that’s adorned bowling shirts for decades. “It’s got that mini folded lapel look. It’s extremely flattering on any guy,” says Isaac Hindin-Miller, a DJ and fashion writer in New York City. “These days, a bold camp collar short sleeve shirt is the best way to show personality.”

Hindin-Miller is partial to the “nostalgic-looking Hawaiian shirts,” like Tombolo’s ‘Hurricane Cove’ Cabana and “the beautiful prints” featured on Blue Blue Japan’s Sakura Tunnel & Mt. Fuji Vacation Shirt.

You should never button the cuffs on an untucked shirt. You’ll look like you forgot to tuck it in.

Patrick Kenger, Personal Stylist

On the button, off the cuff

When it comes to finding the right shirt, the style of the placket (the fabric where the buttons meet the buttonholes) matters. A standard placket shirt — Noguchi suggests 7 Diamond’s Saga Short Sleeve Shirt — has a strip of fabric down the center of the shirt. This is the most common button-down.

The French placket, like Banana Republic’s Slim-Fit Hi-Dri Dress Shirt, is where the fold is underneath the front of the shirt. It’s a bit more formal than the standard placket and is often worn with a jacket or tucked in.

Where the buttons fall on a shirt also matter if you’re going to wear a shirt untucked. If you’re trying to walk the line between casual and formal, Noguchi recommends Johnnie-O’s Hangin’ Out collection, which features a unique “Tweener” button. “It’s an additional button between the second and third button on a shirt. It’s perfect for wearing it untucked,” Noguchi says. “The second button is too buttoned up. The third shows too much.”

Another clue for how to wear a shirt can be found at the end of the sleeve.

  • The most formal cuff is the French Cuff, where the sleeve is folded back on itself and should be worn with cufflinks.
  • Barrel cuffs (more rectangular in shape) or rounded cuffs are more casual.

Cuffs can also provide a guide for how to wear your shirt. “A shirt that’s meant to be worn untucked will be right on the same line as a sleeve cuff,” Noguchi says.

Patrick Kenger, a personal stylist in Scottsdale, Arizona, suggests if you’re going to wear a shirt untucked, it’s important to lean in to the casual style. “You should never button the cuffs on an untucked shirt,” says Kenger “You’ll look like you forgot to tuck it in. Keep those sleeves rolled up two to three cuff lengths.”

Best button-down shirts

The right button-down for you to wear untucked comes down to how it fits. “Don’t wear anything too relaxed or fitted untucked,” Noguchi says. “You want to keep your shape. A super skinny skinny fit might give you a weird bulk. And with relaxed shirts, you don’t want to poncho it.” Here are some highly-rated button-downs in various styles and at various price points to give you an idea of your many options and how to make the most of them.

Everlane’s The Air Oxford Short-Sleeve Shirt (limited availability)

Looking for something that works in the summer? This short-sleeve shirt is made from light-weight cotton. It’s casual thanks to a button-down collar, without being too dressed down.

UNTUCKit’s Wrinkle-Free Performance Short Sleeve

This button-down shirt has a bit of stretch from spandex and is designed to be worn untucked. It’s meant to be washed at home and has slim, tall and relaxed options that fit a variety of different body shapes.

Peter Millar’s Capri Slim-Fit Button-Down Collar Checked Cotton Shirt

“A slim-fit, untucked shirt made of high quality material,” Kenger says about this option from Peter Millar. “Try the slim fit first and work up from there. You’ll likely surprise yourself with what you can fit in.”

Hill City’s Hybrid Denim Shirt

The look of a jean shirt without being boxy. The cotton-polyester blend gives this shirt lightness and the oversized pocket is sturdy enough to hold a few pens.

W.R.K’s Dot Performance Dress Shirt

“It’s a professional look with the comfort of a T-shirt,” says Noguchi about this WRK option. “The shorter hemline means they work both untucked and tucked.”

Buttercloth’s Firestone in Navy/Orange

Buttercloth’s name tells you why people like the shirt. The button-down, which counts Shark Tank’s Robert Herjavec as an investor, is soft and light. A subtle twist of the pattern on the cuff and spread collar help make this shirt more interesting, too.

Gap Stretch Poplin Shirt in Untucked Fit (limited availability)

Gap’s cotton shirt sports a bit of spandex for give and the curved hem makes sure it doesn’t hang too far down when untucked. A chest pocket breaks up the front and can hold a pair of glasses in a pinch.

Bonobos Brushed Button-Down Shirt

This cotton button-down shirt is a bit heavier — good for fall and spring — or if you work in an office where the air conditioner is always on blast (and if you’re in your office at all). This shirt could work jeans, too, both in casual work settings or out and about.

J. Crew Untucked Cotton Chambray Shirt

J.Crew’s take gives you the look of denim without the weight of denim. The chambray un-tucked shirt is made with organic cotton and has sleeves that were meant to be rolled up.

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