When assembling your wardrobe, what styles of shirts are best to buy first? What shirts can you do without? That’s what this list is for. The shirts you’ll want to have on hand at all times (and maybe buy multiples of) will rank higher than the shirts you could probably do without. Also, keep those collars a substantial but not over-sized semi-spread. Button down, cutaway, and tiny-sized collars are great for certain situations, but you just can’t go wrong with a nicely sized semi spread. Specific examples for each are shown below. Pics are clickable.
#1. White, semi-spread, light to mid-weight Poplin/Pinpoint/Twill
Quick, think of a white dress shirt. Yahtzee. That’s the #1 shirt we should all have in our closet. The collar does not button down on these, and they’re made from a mid to lightweight fabric. Some call these “oxfords” even though that’s not quite right. It’s a shirt that’ll look just as good with a suit as it will under a v-neck with jeans. It’s crisp, it’s clean, and you want a collar with enough beef to look substantial. Melt your brain with the differences between poplin, pinpoint, & twill here, here, and here (scroll down a bit on that last one). Head here for a hierarchy of white dress shirt options, from cheap to splurge-worthy. A terrific mid-priced option is this one from Nordstrom. Will need a bit of tailoring, but expect it to go on sale this Friday (7/19) as part of the Nordstrom Anniversary Sale.
#2. Light Blue, semi-spread, light to mid-weight Poplin/Pinpoint/Twill
Pretty much the same thing as the white dress shirt at #1, only in a very pale, light blue color. Not royal blue, not kinda light blue with grey buttons, light blue with standard off-white/bone colored buttons. Slightly less formal than white, but still able to be dressed way up. It’s actually somewhat difficult to find a very pale blue dress shirt for a reasonable price. The Banana Republic option shown here doesn’t even come in Neck & Sleeve measurements.
#3. White, mid-weight to heavy-weight Oxford Cloth Button Down Collar
Honestly? Not a “dress” shirt. At least not most of them, especially if they’re cut in thicker, more rumpled cloth. But still needs to go on the list just because of its versatility. The OCBD (surprisingly, not a member of WuTang) stands for Oxford Cloth Button Down. And the “button down” part refers to the collar, not the fact that you button the shirt in front. A few lighter, pressed OCBDs can pull some duty at the office, but just make sure it’s not that much thicker than a standard poplin. The thicker the fabric, the less dressed up it can get. A workhorse for layering.
#4. White base, blue windowpane / tattersall
Lots of white and blue right? Well, yes. An orange and green check just won’t go with as much stuff in your closet. Meanwhile, a windowpane is just different enough from the usual striped shirts most guys default to. When under a jacket of some kind, they’ll give your look a bit of depth. And unlike gingham (we’re getting there) they’ve got plenty of white which is more business ready. When it comes to the office, for patterns, Tic-Tac-Toe > Checkers. And for the size of the squares, the ideal size is between a pencil eraser and a quarter. The perfect example: Ratio’s.
#5. The Bold Gingham
Color is up to you. Black and white obviously offers the most contrast, but deep blue, red, even purple can deliver. It’s a dressed up version of a dressed down pattern. Nordstrom’s house brand “Calibrate” is shown above, and those shirts are something else. Also part of the Anniversary Sale, coming up on Friday. How to wear it over here.
#6. White base, thin stripe
The stripes on these are razor thin. Not a double stripe of different colors (say, a light blue and dark blue next to each other), but just one color, real thin, evenly spaced. That white base is dominant, but the stripes add a bit of depth. Clean and mean. Thicker striped ties look just fine worn over these. Keep your stripes slim and you can even take some color risks like a pink or light green.
#7. The micro pattern
Whether it’s a tiny check, tattersall, micro-plaid, gingham, or houndstooth, these are shirts that have two (three max) colors going on with a very small pattern. Not stripes, but something more geometric. From a distance they look solid, but up close they’re not. Lots of visual depth with these, and they often look great when you wear a suit without a tie.
#8. Thick/Bengal stripe
The stripes here are much thicker than the pin-stripe at #6. Thick enough that from a distance, the shirt looks like it’s leaning more towards the color of the stripe, instead of the white base. Blue is a default, black stripes can work, as can red if you want a shirt with some punch.
#9. The Pink or Red Subtle Patterned Shirt
Pretty sure we’re all past the pink = YOU PLAY BALL LIKE A GIRL thing. Beware though. Some of us whiter dudes (y’know, us crackers) might not look so great wearing solid pink. Lil’ too close to the skin tone. So, harken back to #7, and maybe opt for a red micro-check on white. That’s not a bad option for a similar look. It helps make the pink look less like flushed flesh.
#10. The Grey
A grey shirt with collar stay slots (not a floppy collared chambray) is a good shirt to have on hand for under black sweaters or black sportcoats/blazers. Works surprisingly well with a navy suit as well. Not a bad getup to wear when grabbing a cocktail post sunset. It’s still put together, has an evening out feel to it, but it’s thankfully still very far from clubby when tucked in and layered over.
- 2 is the magic number: Less is more. Two is sort of the speed limit when it comes to dress shirts. Meaning: Anything more than two colors or two different thicknesses of lines in a pattern on a shirt and things can get weird. There are exceptions, but solids, and pattern shirts with just one color on a base are safest.
- Try and stick with all cotton: Prices are rising (evidence is up above…) but limiting the level of poly used in your dress shirts will keep you cooler. Sometimes synthetic just can’t be avoided, like in the shirts from Target.
- Neck and Sleeve = More dressed up: Sometimes a S/M/L/ neck will fit. Sometimes it won’t. Try it on.
- No-Iron is up to you: Some people love wrinkle free. Some hate it. Up to you.
- Collar Stays: Always. Unless it’s a button down collar. Wurkin Stiffs are even better.
Anything missed? What should have made the top 10 that wasn’t? A bit plain + boring? Maybe. But again, two is the magic number. Extra colors + thickness of stripes can make a nice shirt look cheap real fast. Plain isn’t necessarily a bad thing. Leave it all in the comments. Many thanks to Rietsh P. for sending in a request for a 2013 update to this list.