21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (2024)

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This season, push all the right buttons.

By Avidan Grossman and Michella Oré

21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (4)

    If you spent the better half of this morning haplessly googling “casual shirts for men”, it’s probably time to refine your search. In part, that’s because “casual” is a term of frustratingly imprecise nature. Casual relative to what, exactly—and according to whom? An Oxford-cloth shirt with a button-down collar might feel more casual than, say, a gingham dress shirt, but it’s the former we’ve been wearing most, often with our grooviest ties. (We don’t know who needs to hear this but...you’re better than the gingham dress shirt.)

    The exasperating nature of your search also has to do with the fact that the very meaning of casual, especially as it pertains to the way we dress, has never been more in flux. These days, wearing a shirt at all—y’know, one with a collar and buttons—constitutes its own form of rebellion. And when you’ve spent the last eight quarters fielding emails in a rotation of ratty, threadbare tees, the shirts you once considered the height of casual cool likely feel downright stuffy in comparison.

    Thankfully, we’ve been covering the button-up beat with the urgent attention it demands for years, making us uniquely positioned to answer all your hard-hitting questions about the best casual shirts for men. And answer ‘em we did, in the form of 23 pitch-perfect options you can get your hands on right this very minute.

    Eager to learn more? Check out the rest of our culture-shifting shirt coverage here.

    All products featured on GQ are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (5)

      1/21

      Alex Mill fine wale corduroy popover shirt

      Throw it over a turtleneck, and you've got your wine-night-poetry-set look down pat.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (6)

      2/21

      Todd Snyder long-sleeve merino polo shirt

      The worst-kept secret when it comes to staying warm and looking, like, 50% hotter in the process? It's this guy right here.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (7)

      3/21

      Our Legacy jassy hypnosis shirt

      Put them in a trance with a button-up that looks decidedly of-the-moment retro, not dated.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (8)

      4/21

      J.Crew medium weight denim shirt

      A denim shirt with a lil' extra weight so you can keep the Canadian tuxedo alive once winter hits.

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      5/21

      General Admission jacquard wool shirt

      That traditional Scottish tweed will add level of dimension and refinement to even the most chilled-out look.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (10)

      6/21

      Uniqlo extra fine cotton broadcloth long-sleeve shirt

      How do you straddle the line of casual office garb while still looking put together enough to nail an impromptu presentation? This shirt, right here.

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      7/21

      Eckhaus Latta "Cobra" shirt

      It's an eternal summer (at least in your head).

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (12)

      8/21

      Stüssy cord zip shirt

      Cold weather and buttons are a disastrous combination. Zip up this guy when it's freezing out and give your digits a break.

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      9/21

      ERL metallic checked-taffeta shirt

      You're the gift this season, so dress like one.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (14)

      10/21

      Commes des Garcons grosgrain-trimmed checked shirt

      The thick-trimmed pockets and hem take this shirt from pencil-pushing professional to plain old professionally cool.

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      11/21

      Corridor duck dye overshirt

      Exactly what you want in an overshirt, from a brand on the nexus of the nice, normal clothing movement.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (16)

      12/21

      Levi's "Barstow" Western denim shirt

      Yes, the goes-with-everything white whale of button-ups you’ve been chasing your whole life is out there, and its name is the denim shirt.

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      13/21

      L.L.Bean chamois flannel shirt

      On the eve of its 100th birthday, L.L.Bean’s legendary chamois shirt—the unofficial uniform of East Coast dads lugging the toolbox out of the garage to fix that leaky faucet, dammit—looks better than ever.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (18)

      14/21

      Sondér "Cooper" overshirt

      A thick wool overshirt is slickest way to stay comfortable this time of year, which is what casual is all about, right?

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      15/21

      Brooks Brothers classic fit original polo button-down shirt

      Brooks Brothers helped introduce the Platonic OCBD, originally designed to prevent shirt collars from flapping around on the polo pitch, to the American masses. After all this time, the centuries-old brand still sets the standard.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (20)

      16/21

      Drake's check wool two-pocket work shirt

      The London-based brand has been all about "relaxed elegance" since its inception in the late '70s, so you know you're in extremely good hands when it comes to any of its shirting selection.

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      17/21

      Everlane relaxed poplin shirt

      If your idea of casual skews more “rooftop drinks” and less “park hangs”, a crisp poplin shirt will always serve you well.

    • 21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (22)

      18/21

      Thom Browne tartan check shirt

      Thom Browne's signature stripes might drum up the most buzz, but this cozy tartan shirt is a stellar example of what you get when the cheeky prepster takes on workwear.

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      19/21

      Wax London "Beck" rudgy shirt

      Cut from organic cotton with the relaxed fit of your favorite striped button-up—and with the same inimitable polish.

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      20/21

      RRL indigo denim workshirt

      Slightly heftier than chambray but way more laid-back than regular ol’ cotton, denim in any form should be your foolproof ace in the hole when it comes to casual dressing.

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      21/21

      Gitman Vintage cotton/linen shirt

      With a shirt this dynamic, your outfit will practically take care of itself (but if you're looking for a styling recommendation, tucking it into a loose pair of denim or some sturdy chinos is a great place to start).

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    21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (2024)

    FAQs

    How many times should you be able to wear a shirt? ›

    T-shirts, tank tops and camisoles should be washed after each wearing. Outer clothes like dress shirts and khakis can be worn a few times before washing unless it is hot out and you are sweating or they are visibly dirty or stained.

    How many T-shirts should a man own as a minimalist? ›

    When it comes to shirts in a minimalist wardrobe men need to understand that quality triumphs over quantity. Aim for a collection of around 5-7 shirts, including both casual and dress shirts. Opt for neutral colors like black, white, light blue, and gray – they're easy to mix and match.

    Is it OK to wear the same shirt 3 days in a row? ›

    There's no hard and fast rule for how many times you can wear clothing again, but experts say there are a few types that should be washed after every use: underwear, socks, tights, leggings and activewear. This advice also applies to any other clothes with stains, sweat, odor or visible dirt, Mohammed said.

    Why do we need to wear proper clothes in every occasion? ›

    Dressing appropriately can make you feel comfortable, confident and professional. It can also help you fit in with the social norms and expectations of different events. The color, fabric, style and accessories of your outfit can also affect how you look and feel.

    Can you wear t shirt twice? ›

    Button up shirts are usually good for 3-5 days of use before they need to be washed. T-shirts can only be worn once or twice because they lose their form. Socks and underwear generally get washed after each use, but sometimes a pair of socks will be good for a second day if I only wore them for part of a day.

    What is the 30 wears rule? ›

    What is the 30 Wear challenge? The 30 wear challenge is a commitment to wearing a new item of clothing at least 30 times. It forces you to pause before clicking buy and ask yourself, 'will I actually wear this 30 times?” If the answer is not 100% yes, then you don't make the purchase.

    How many t-shirts for men? ›

    A dozen of t-shirt is enough for a guy! No matter how many T-shirt you own, you always wear 3/4 of them.

    How long should a t-shirt be on a man? ›

    Shoulders: seams should sit on shoulder-bone. Sleeves: they should be mid-length on biceps and not too loose. Length: a T-Shirt should end middle of fly. Width: ideal when you leave 2.5-5cm loose fabric on each side of the torso.

    How many shirts does the average guy have? ›

    It is difficult to give an exact figure of how many dress shirts the average guy has in his wardrobe. Typically, if we exclude all other types of shirts and only focus on proper dress shirts, then the number of dress shirts the average man owns is probably around 10 shirts, give or take.

    How often should I change my T-shirt? ›

    T-shirts: after every wear

    T-shirts grab onto our skin's oils, sweat, and any outside dirt we come into contact with each day. This makes them a hotbed for bacteria and odors, so it's best to throw them in the laundry basket after a single use.

    How many times can you wear pajamas before washing them? ›

    The Experts Weigh In

    The American Cleaning Institute, however, is a little more lenient with its suggestions, recommending that pajamas are washed after three or four wears. Good Housekeeping magazine says once a week is the longest you should go.

    How many times can you wear the same jeans? ›

    A good rule of thumb is to wash your jeans after every 3-10 wears, or when they start to smell. If you're regularly active in your jeans (think: manual work, anything where you work up a sweat), wash them every 3 wears, but if you're working at a desk, you can probably go through multiple wears without washing.

    What do we wear on special occasions? ›

    Types of clothes for different occasions,

    You must dress elegantly for formal events such as weddings, gala dinners, or award ceremonies. Women can choose from options like floor-length gowns and co*cktail dresses with heels, while men should wear suits with ties or bow ties.

    How many times in a row can you wear a shirt? ›

    In the U.S., it's expected that you wear a different shirt every day of the week, but, in other some countries, it's common to wear one shirt for a few days before changing it. If you wash the shirt and wear different pants or skirt and accessories, you could wear it two days in a row or a couple of days later.

    How many times can you wear the same Tshirt? ›

    T-shirts and tops: after one wear

    You should treat your t-shirts like underwear because they are in a very close contact with your skin and absorb the biggest portion of sweat. Wash them each and every time after wearing them. The only exception is if you were wearing it for one hour or less.

    How many times can you wear a shirt in a week? ›

    In most cases, you can wear the likes of work clothes up to five times before they need to be washed. Things like a suit can be worn multiple times, button-down shirts can usually be worn up to four times and pants can last for up to five wears as well before washing is necessary.

    How many times can you wear the same shirt in a week? ›

    Shirts typically 1 day. Jeans 2 or 3 days unless they get too dirty and if you look it up it is recommended to do so. Shorts also 2 or 3 days depending. Laundry: How many times do you wear an article of clothing before washing it?

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