The transition of seasons, the drop in temperature, and the faint sounds of jingle bells in the distance are all indicators that now is probably a great time as ever to give your current shirt collection a refresh. Don’t worry; we are not talking about all your shirts, just ones you have been living in, on rotation for the last two years.
Casual shirts, or basics, as they’re often called, are essential for every man, no matter what your age or where you work, because just like the name alludes, you can literally wear and layer it with everything. However, there will come a time when you might have worn something so much; it’ll inevitably have to be demoted to your only-worn-at-home-or-on-errands pile.
So right on cue, just like a present being delivered straight into your wardrobe, we’ve compiled the best casual shirts to help bridge that flexible-working and semi-sociable gap.
Outerknown Blanket Shirt
BEST OVERALL
This may not be the OG blanket shirt, but the brand is known for saving the Earth a little bit every time it makes another garment, so it might as well be. This shirt is perfect for just about any activity that calls for ultimate casual comfort. Crafted from heavyweight organic cotton twill with buttons made from naturally fallen tagua palm nuts, the Outerknown Blanket Shirt is durable enough to be your go-to work shirt but soft enough to throw on and wear around a chilly house all day long.

Goodthreads Red Plaid Twill Shirt
BEST CLASSIC
Nothing says smart and casual like a red plaid shirt, and this 100% cotton pick from the Amazon fashion brand Goodthreads marries the two styles seamlessly. Cut in a slim-fit shape; this button-down could be paired with a number of your current favorites, thanks to its rounded hem and inoffensive buttons. Great for the WFH week or weekend walks.
Read more: Coolest Flannel Shirts

Amazon Essentials Standard Navy Shirt
BEST BASIC
For those days when you’ve overslept or moments when you are trying not to look like you’re trying too hard, this navy Amazon Essentials shirt should fit the bill. Made from 100% cotton, this long-sleeve top will ensure you look the part whenever and wherever in a slim-fit style.
Read more: Best Henley Shirts

J.Crew Garment-Dyed Harbor Shirt
BEST ORGANIC
The harbor shirt from J.Crew was made for flexible working, crafted from sustainable organic cotton with the comfort of a casual T-shirt. This button-up thrives by continuous wear, and thanks to the garment dye effect, it will subtly and softly fade over time.

Tommy Bahama Sea Glass Breezer Linen
BEST LINEN
Linen isn’t just for warm weather but can also be worn layered up during the colder months, making it an easy and lightweight transitional piece. This bubblegum pink option from Tommy Bahama is adorned with a single front pocket, contrast buttons and a curved hem that can be teamed with a thick sweater or a leather jacket.

UNTUCKit Brandford Vintage Wash Shirt
BEST PLAID
The Brandford offers a touch of maturity to your standard red, white and blue plaid shirt. Released within UNTUCKit’s fall collection, this vintage wash piece made with 100% cotton gives a fresh take on a classic while offering their same beloved softness. Pair it with a suede jacket and faux leather pants for a laid-back vibe.

Levi’s Barstow Western Shirt
BEST DENIM
There’s a reason denim doesn’t go out of style; because it goes with literally everything, from chinos to double (or even triple) denim. It can do no wrong. The Barstow Western pick from Levi’s is a prime example, designed in a standard fit with a point collar; this is an item that will live in your wardrobe indefinitely, so cut off the tags and shred the receipt.

Bonobos Knit Button-Down
BEST T-SHIRT REPLACEMENT
Bonobos takes comfort to another level with its knit button-up shirt. Imagine your favorite jersey T-shirt or better yet, those comfy cozy jersey sheets you don’t want to leave in the morning, and then make them into a fashionable, functional piece of clothing that can pass for office-appropriate even on the days that aren’t labeled “casual.” The cotton-polyester blend allows easy movement and is built to last a long time.

Mack Weldon Vesper Polo
BEST POLO
When in doubt, a neutral polo can help you out, and this particular style from Mack Weldon is ideal for weekday Zoom meetings or weekend trips into the office. Made in a combed cotton and modal blend, this soft knit short sleeve top gives sports-luxe a whole new meaning.

L.L.Bean Kennebunk Sport Shirt
BEST WRINKLE-FREE
After a long journey or a long week, the last thing you want to do is get the iron out, cue the L.L.Bean Kennebunk shirt, which comes in a range of colors, is made from 100% cotton poplin, and features a wrinkle-free fabric — yes you read correctly — that doesn’t wash out and keeps moisture away from your skin. This wrinkle-resistant option seems like a perfect OOO, a first date, or even a first-day-on-the-job kind of shirt.

Patagonia Sol Patrol Shirt
MOST SUSTAINABLE
Now bear with us; this might say it’s for fishing, but the Patagonia Sol Patrol made with fast-drying polyester fabric, and 50+ UPF sun protection is ideal for adventure and travel enthusiasts. Also, with 64% of the fabric using recycled materials, it’s like you are giving back to the planet with every wear.

The 20+ Most Comfortable Men’s T-Shirts on the Internet in 2021
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