The Only 3 Shirts You Need For Fall

Like most internet weirdos who spend their free time writing about clothes, I love this time of year.

I naturally prefer colder weather to warmer weather, so I always look forward to when I can officially say goodbye to mosquitoes flying into my ear and not having to worry about my glasses sliding off my sweaty face.

With the changing weather, I get excited to wear different stuff. I get this feeling during the transition between any of the seasons, to be honest.

I realize, though, that most normal people find it to be a nuisance to have to start deciding to dress in a different way than they have been over the past few months to fit the oncoming weather shift. It’s just another thing on your plate. Also, having too many options causes our brains fatigue.

This is why I decided it would be helpful for me to lay out the only three shirts you need for fall. All three options straddle the line between “casual” and “nice”, meaning you will look like you put in some effort but won’t look out of place wherever you go.

A few notes: I excluded undergarments and “over”-garments, meaning I didn’t put t-shirts on this list because I presume you already own some t-shirts. I also excluded things like flannel shirts, “shirt-jac” style shirts, and sweaters because it’s not really cold enough yet for those. It’s this odd cold-hot-cold-hot weather that poses a challenge.

These are the only shirts you need to tackle 90% of your fall adventures.

#1 – Denim Shirt

Ah, the venerable denim shirt. Last year I wrote an article about my beloved denim shirt and how it’s pretty much the perfect shirt. My opinion has not changed. I find it to be perfect for almost any scenario that isn’t too formal. Some denim shirts are more western-leaning, meaning they may have pointed yokes or turquoise snap buttons. Those shirts are definitely awesome and you can more than likely swap in one of those to use as your “denim shirt”. But for my money, the most versatile style would be a button-down collar and single breast pocket without any other ornamentation or embellishment.

The reason for this is so you can throw a sport coat over the top if you need to. Some of those western shirts are a little too casual to look passable under a jacket (even a tweed jacket), but a simpler style looks quite dashing under a soft tweed. 

Because denim is such an inherently casual fabric, you can wear this shirt untucked literally anywhere you would a t-shirt. No one will bat an eye, but you WILL look better than the majority of other men.

It’s also very durable and hides stains well, which means you don’t have to be precious about it. You can go hiking with your kids and not worry about your son wiping dirt on you. You can cook those greasy burgers and not worry about splattering grease. It’s light enough so you won’t sweat like a beast during the day, but thick enough to keep you warm in the evening with your sleeves rolled down while you have a beer with your wife on the deck once the kids finally fall asleep.

My denim shirt is from J. Crew. They are currently selling it in a traditional fit, which is only slightly wider in the body than my slim fit.

Also, just FYI, I don’t get any commissions or kickbacks for adding links or recommending products.

#2 – Rugby Shirt

I have only fairly recently jumped on the Rugby Shirt Train. My wife got one for me about a year ago and I absolutely love it. It’s like if a long-sleeve polo shirt lifted weights and ate more red meat.

This isn’t a shirt you would wear under a jacket, which makes it slightly more limited than the denim shirt. But it looks masculine with jeans and its Ivy roots would cut the mustard at any business-casual office if paired with khakis and loafers.

My version is from J. Peterman and I think they really nailed it. The cotton is thick. The collar is a smaller spread style. The sleeves are a little long, which means I can extend my long arms without the cuffs riding up. I feel like I could actually play rugby in it.

Contrast that with a version Brooks Brothers did last year (which I believe they have wisely discontinued, as they are no longer on their website). Their version had their iconic oxford-cloth button-down collar. And while it looked kind of cool, who would want a button-down collar on a shirt ostensibly made for playing a contact sport? Those buttons would get ripped off in two seconds. It would be like if my Brazilian Jiu-Jitsu gi had a button-down collar. The Brooks Brothers version just screamed “inauthenticity”.

With that in mind, don’t be precious when you wear a rugby shirt. It’s made to get dirty. A perfectly clean and pressed rugby shirt just looks weird.

#3 – Oxford-Cloth Button-Down Shirt

Sorry guys, you can’t escape it. The OCBD is always there. It’s always following you, like a zombie or a Terminator.

I am sure every article you read about shirts talks about how amazing OCBDs are. And they’re right.

This is the slightly more formal version of the two other shirts on this list. This is the shirt you need for heading into the office. This is the shirt you need for your annual performance review over Zoom or Teams. This is the shirt you need for the parent/teacher conference. This is the shirt you need for church. This is the shirt you need for your dinner date.

This is the shirt you need for showing your kids how an adult man dresses. It’s a style that spans all income levels and social strata.

My maternal grandfather was an engineer who went to MIT. He always wore an OCBD.

My paternal grandfather was a guard at Rikers Island who bragged about never having read a book in his life. He always wore an OCBD.

An OCBD is for when you need to look put-together but not stuffy. It’s for when you need to have a glass of wine with your dinner guests but then roll up your sleeves and chuck a football around the yard with the kids.

It’s a shirt for being taken seriously.

In my opinion, an OCBD shouldn’t be expensive. I’ve written before about the things in your wardrobe you should and should not splurge on and the OCBD is one area where you can save your money. Even though this is a nicer looking shirt than the others on this list, it’s still a fairly rough-and-tumble style. So don’t go nuts spending crazy dough on the perfect fit or collar roll.

I have some OCBDs from Lands’ End, Brooks Brothers, and Charles Tyrwhitt. The Lands’ End Hyde Park versions are the best, but they now only use S/M/L sizing instead of the specific neck and sleeve sizing (which is a bummer). Brooks Brothers is doing this too, which is unfortunate.

I know there are tons of better shirts out there (Kamakura, Spier and Mackay, Proper Cloth) but that Hyde Park oxford is on sale right now for $12. If you’re looking to make OCBDs a part of your rotation, you can’t beat $12 (as long as the fit works ok for you).

The fabric of the Lands’ End OCBD is what sets it apart. After a while the thick cotton softens and almost feels like clay. The Brooks Brothers version is a bit thinner and feels more like a “dress” shirt (although it has a better roll to the collar and works better with a tie). The Charles Tyrwhitt version has a pretty small collar which doesn’t work at all with a tie and the fabric is a bit stiff. Still fine under a sweater or untucked with the sleeves rolled up, though.

As far as color goes, your best bet is either light blue or white. I wear both equally.

So that’s it! Three great shirts and they are all you need for fall. Keep them in your closet and rotate through them while the weather is figuring out what season it wants to be.

You’ll be the most stylish dad getting juice spilled on him at the playground.