My Hunt for the Perfect Oversize White Button-Up

What jumped out at me immediately with the AYR Deep End — aStrategist favorite— was the color of both the shirt and the buttons. The shirt appeared extra white, and the buttons seemed to have an almost yellow tint to them, making the shirt as a whole feel more modern than classic. Though the fabric was supersoft, it wasn’t as thick and sturdy as I was hoping for. The oversize fit was fine, but the sharp edges and large size of the front pocket didn’t do it for me. I would be curious to try this shirt in another fabric, like the denim, as the fit overall worked. I took a medium and liked where the shoulders hit, and the bottom had a slight shirttail to it that I liked. But between the stark white and giant pocket, the Deep End didn’t make the cut.

I went to the Buck Mason store in Nolita to try on the Mainstay Cotton Shirt, which the sales staff tell me is a perennial favorite among them and their customers. Though it had potential, the fabric was too light for what I was looking for, as it was bordering on sheer. While the cut was nice, the medium I tried on was slimmer than some of the other shirts on this list, and, for me, an oversize fit is key.

I really wanted to love this shirt as I’ve historically been a big fan of Everlane, but it wasn’t oversize, which was my main criterion, and the fit overall felt too formal for my taste and needs. Though it would be a nice shirt if I were to wear it under a suit jacket for the office, it didn’t feel like something easy to throw on for everyday wear. The fabric was a nice, classic oxford, however, which I liked. I tried on the size six, which fit really well.

Online, the shirt looked as though it would check all my boxes — especially since Ralph Lauren is known for its button-ups — but in the end, it wasn’t as oversize as I was looking for. The thick oxford material was spot-on, however, and I did like that there wasn’t a pocket on the chest since it gave the shirt a cleaner look. Most shirts I tried on and tested didn’t have a logo, but this one did. In most cases, that would be something I’d avoid, but I was willing to make an exception for Ralph Lauren. I ordered and tried on a size small but do wonder if a medium might fit in the way I was hoping it would, based on how it’s cut on the model.

I revisited the shirt I bought last summer, wondering whether what I was looking for had been sitting in my closet all along. Though I do still like it, I found it to be too thin and flimsy. The lightweight material works really well on hot days, but it doesn’t have the heft or truly classic feel I was looking for. I wear a small, which was just the right amount of oversize.

I was pleasantly surprised by both the fit and quality of this shirt. I’ll admit I expected to not like it — it didn’t jump off the page at me when I was ordering it online. But the oxford cloth had a great hand, both soft and hefty, and the fit was generous but not in a way that made me feel as if I were drowning. The collar was my favorite part because it really held its shape and gave the top of the shirt some definition that I liked. What I didn’t love was the giant front pocket, which felt very similar to the AYR shirt and was a bit too pronounced for my liking. I ordered a medium, which was the right call.

This would have been a winner if it were in oxford cloth instead of poplin. I loved the fit — just oversize enough — and the striped detail at the bottom of each side was a fun touch. The dropped shoulder was pretty much perfect, and if I were in the market for a poplin version, this one would be nice: not too thin but still lightweight and breezy. It gets bonus points because Alex Mill cuts this in a bunch of different colors every season and will sometimes bring in new materials. I tried on the medium, which is what I will buy when I inevitably go back for it.

Perusing the racks at COS recently, my interest was piqued when I came across a pretty basic white shirt. I had to try it on despite it being poplin. Like the Jo Shirt from Alex Mill, this would have been a winner had it been in my desired fabric, but it will remain on my watch list as the weather warms. The fit was nice — I tried on a six — and I liked the size of the pocket and rise of the collar. It felt classic, just cooler owing to the relaxed fit. Petition for COS to make this in oxford cloth next season, please!

I ended up loving this shirt so much I bought it in three colors. The fact that it seems to always go on sale helps, but ultimately I ended up preferring the Étienne’s very oversize fit to nearly everything else I tried on. Though the material wasn’t that heavyweight oxford cotton I had my mind set on, the cotton is still substantial enough to hold its shape and not look too drapey and flimsy. I ended up with my normal size, small, though it’s oversize enough that I could have sized down. I even had the white one embroidered as an extra, personal touch. Because it’s so oversize, I have to be careful with what I wear it with. Anything too big on the bottom makes the bigness of the shirt feel frumpy, but paired with my uniform of straight jeans and loafers, it’s perfect. I especially like the classic men’s locker loop and front placket that’s slightly V-shaped, which add a more interesting touch. Because of the extra volume, the Étienne has a more casual feel than the Sézane Max (see below), and I tend to wear it more on the weekends.

My reaction when I first put this on was,Damn, this is good. The fabric was as traditional and thick as I was hoping for, and the oversize fit was generous but I didn’t feel as though I were drowning. I liked that the chest pocket wasn’t a basic square, and the cuffs stayed where they were when I rolled them. I took a size 38, which Sézane says equates to a medium or U.S. six. Though it’s oversize, it’s less so than the J.Crew Étienne and not so big that I wouldn’t wear it with wide-leg jeans. And with my regular denim and loafers (or heeled boots in the winter), it’s ideal for that easy-to-throw-on ensemble, especially on days when you want to feel put together but getting dressed is hard. I like wearing this shirt under a blazer and to the office.