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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      7/21

      Eckhaus Latta "Cobra" shirt

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

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      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.

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      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.

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      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.

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      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.

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      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.

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      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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