I recently did an “ask me anything” over on my Instagram stories. Someone asked me, “How many shirts are in a sensible wardrobe?” My answer was simple: “You’re asking the wrong person. There’s always another one. If it feels right and gets worn, that’s enough.”
Some people like cars, some like baking, some like guitars. I like button-downs. I love seeing how they age, washing them, breaking them in, and watching them turn into pieces I reach for again and again.
This time of year is the perfect excuse to keep wearing button-downs, but also to bring out their warm-weather cousin: the popover.
The popover can be divisive. It’s not a polo shirt, a T-shirt, or a full-placket button-down. It’s its own thing, a shirt that you pull on over your head, somewhere between casual and smart.
There’s something about the popover that really captures the spirit of mid-century Americana for me. I picture summers on campus, surfers on the West Coast, and NASA engineers working against the clock to get to the moon.
Earlier versions could be found in 1920s to 1940s sportswear and workwear, where the half-placket reduced bulk, lowered production costs, and gave a cleaner front for activities like tennis, golf, or just casual wear.
The style also turned up in military shirts, especially summer and tropical uniforms, where the pullover design created a neater look when worn without a tie.
That mix of practicality and style is exactly what makes the popover so appealing to me today. It’s a shirt with history, but also one that still feels fresh when you get the details right.
For my latest collaboration with Proper Cloth, I set out to create three shirts that nod to that mid-century era while still feeling at home in today’s wardrobe. Each one is made to measure, but with its own subtle differences, each referencing a different side of mid-century Americana.
The Campus Classic
I’m calling this first one the Campus Classic. It’s a straightforward Oxford cloth, just a touch wider than a traditional university stripe, but still firmly rooted in the spirit of classic ’60s menswear.
It features a perfectly soft, unstructured collar and a single flap pocket — details inspired by old J. Press and Brooks Brothers adverts from the era.
Every detail speaks to that era I’m drawn to: simple, functional, and worn without fuss, yet still unmistakably sharp.
Blue Collar Ivy
This next shirt I’m calling Blue Collar Ivy. It brings together a mix of Americana influences into one piece. It reflects my love for Ivy style, Western wear, and American workwear, all combined.
I was especially pleased with the shape of the pockets: two flat pockets with rounded edges, very much in the spirit of classic American workwear shirts, which typically came on full placket designs. But here, I wanted the Ivy influence to come through in the popover style of the shirt itself.
For the fabric, I chose a lightweight blue slub weave, a nod to the kind of material used in traditional workwear. Bringing that fabric into a popover shirt felt like the perfect way to capture the workwear aesthetic while staying true to Ivy.
Feelin’ Fatigue
The next shirt is cut from an American patina fatigue Oxford, a cloth with a subtle texture and depth of colour that nods to vintage military fatigues. It’s inspired by how jazz musicians not only embraced Ivy style but also brought a wider palette of colours into the mix.
I’ve kept the design minimal, letting the deep green colour do the talking. It pairs especially well with brown loafers or warm tones, like the red Shoes Like Pottery sneakers I’m wearing in this picture. This one features just a single patch pocket, keeping things classic and understated.
So, there are the three shirts I’ve created. Each one reflects a different aspect of Ivy style that I love—whether it’s the classic roots, the Americana influence, or the military heritage. I hope they show how Ivy has evolved over the years, with everyone who picks it up bringing their own unique take. That’s exactly what I wanted these shirts to do.
With Proper Cloth, you can create your own shirt from start to finish. If you’re not going for one of their original designs, you can customise everything from the fabric and buttons to the size, shape, and collar style. Literally everything. You can even have your name embroidered on the collar if you wish.
If you want to create your own shirt, simply follow the link here to view my curated gallery.
Don’t forget to use the discount code TOMHOY10 to get 10% off your first order.
One last thing..
Quite a few people have asked the easiest way to create their own shirt from scratch. Simply follow the guide here.
Designed, you say? I think this statement, attributed to Julia Child is relevant here “It’s not cooking, it’s just shopping”.