Six Things I Look For in a Good Dress Shirt

Yesterday I bought a good dress shirt. Yes, it’s purple, but you’re going to have to deal with that. It’s from Jones New York (amusingly, I can’t find any men’s clothes on their website), and I got it at the Bay. After wearing it last night, it occurred to me that it had pretty much everything I look for in a dress shirt.

Thick, opaque cotton

I see plenty of dress shirts that are made of this thin polyester/cotton blend that’s vaguely translucent, particular in light blue or white. I’m kind of a hairy dude. In a strong light, I don’t want to be able to see my chest hair through my shirt.

Removable collar stays

Collar Stay

Collar stays are one of the hallmarks of a well-made shirt. They say “I’m serious about keeping your collar straight”. Plus, it’s cool to have a shirt with removable parts. Just remember to take them out before you send the shirt to the dry-cleaners. I frequently forget this. The plastic collar stays come back as sad bent little things, good only for, I don’t know, shoveling cocaine, maybe?

Enough length

One way lousy shirts cheap out is by trimming the volume of cloth that you tuck into your trousers. Be wary of this, because the last thing you want is to have the shirt creeping out at your hips.

French cuffs

Cuff Links

Obviously these are more of a stylistic choice than a indicator of quality, and only a few of my shirts have this feature. That said, I don’t see many cheap and cheerful shirts with French cuffs. Cuff links can be fun for an otherwise accessory-free man like myself. They’re earrings for your shirt.

Seamless placket

Seamless Placket

This is another personal preference, but I think a shirt looks crisper and a little more formal without the extra stitching and fabric of placket. I’m no opposed to plackets per se, but if I’m looking for a shirt to wear to business functions, cleaner lines are better.

Horizontal button hole

Horizontal Button Hole

If there’s a litmus test for a good dress shirt, it’s the horizontal button hole. I’ve written about this before, but I’ve never had a bad shirt that had this feature. It’s a tiny detail, but it implies that someone cares enough about crafting the garment to make this effort. Bonus points if the thread used on the button hole is a different colour than the rest of the holes (not the case with this shirt).

There are other shirt-related topics. Obviously if the shirt has a lot of loose or unfinished threads on it, stay away. I’m not a fan of monograms anywhere–they just strike me as odd little coats-of-arms. Your shirt should be cut round at the bottom, called a ‘tail’, unless you’re planning on wearing it untucked. In that case, I think having it cut square usually looks better.


  1. Hear hear, though since I only own one pair of cufflinks (I think, maybe around here somewhere), I don’t go for the French cuffs. Nor do I have much occasion to wear dress shirts except, oddly enough, in some incarnations of my rock ‘n’ roll band — which is also the only place I wear my tuxedo anymore.

    You’d think a good dry cleaner would remove the collar stays and replace them after pressing, by the way. But I usually wash mine here at home and hang them (and iron, if needed), so running the stays through the wash is my problem.

    Here’s a good tip if you travel a lot, by the way: you can have your shirts laundered or simply pressed before you go or at a hotel, but ask for them to be pressed folded rather than on a hanger, so you can pack them right up in your suitcase or whatever. Or drop a few in a desk drawer, Don Draper-style.

    I’ve never done that, but I read it somewhere and it made a lot of sense.

    So, next topic: neckties?

    1. Ireland, from about 7 years ago. They’ve lasted, though sadly they’re not actually functional.

  2. There’s nothing like an array of finely appointed dress shirts & although it took me several over-a-hundred-bucks-trifiling-transactions (for a single shirt), I’m stoked to share with you my latest OCD fad….Charles Tyrwhitt; reasonable price point for a supremely crafted garment. I need to figure out however, how to STOP only-all-white buying…I need more therapy; I know. Peace.

    1. It’s actually the horizontal one that’s important. From the old blog post I linked to, which comes from Metafilter:

      “Because horizontal buttonholes take horizontal stress with less deformation of the buttonhole shape and offer much less likelihood of the button pulling out from such stress than do vertical ones.

      But this results in the button being pulled to the end of the hole rather than staying centered. Since a well fitted shirt shouldn’t naturally have any fitting stress across its width above the waist, the custom is to prefer vertical holes with centered buttons above the tuck-in level; they look better, especially on a vertically striped fabric. Below the belt or at the waist, where there might be more stress, you can revert to the stronger position…and demonstrate that you (the maker) are willing to take the time to shift the shirt to change the placement of the hole, further proof that your expensive shirt is worth the money.”

  3. A good roundup! A lot of the same applies to women’s dress shirts too.

    Have you ever tried Etro shirts or Thomas Pink shirts? They make some fabulous dress shirts for men 🙂

  4. why is one buttonhole vertical and the other horizontal or am I seeing things? Hold on to those cufflinks. They are keepers.

  5. Great review! I too like these dress shirts and wear them petty much exclusively. All the points you listed were exactly what I was thinking that makes these shirts great, but you were able to write it down very eloquently. Another great thing about them is they are nicley fitted and the second button from the top is not too high or too low to enble you to wear them without a tie in a dressy casual fashion. The sad thing is that I think they are exclusively sold at The Bay. Is that true? Do you know if they are sold in any othr stores? Thank you.

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