The White 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.

The Light Blue Poplin/Pinpoint/Twill
Pretty much the same thing as the white dress shirt at #1, only in a very pale, light blue colour. Not royal blue, not kinda light blue with grey buttons, but light blue with standard off-white/bone coloured buttons. Slightly less formal than white, but still able to be dressed way up.

The White Oxford Cloth Button Down Collar
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 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 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. When it comes to the office, for patterns, Tic-Tac-Toe > Checkers. For the size of the squares, the ideal is between a pencil eraser and a quarter.

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.

The Micro Pattern
Whether it’s a tiny check, tattersall, micro-plaid, gingham, or houndstooth, these are shirts that have two (three max) colours going on with a very small pattern. No stripes, but something more geometric. From a distance they may even look solid, but up close they’re not. Lots of visual depth with these.

The Thick/Bengal Stripe
The stripes here are thick enough that from a distance, the shirt looks like it’s leaning towardsthe colour of the stripe, instead of the shirt’s white base. Blue stripes are the default, but other colors can work while packing some punch.

The Dressed up Chambray
In ten years we might look back and say “the hell were we thinking?” but for now, a shirt that looks like a denim, yet is much lighter weight with the crispness of a dress shirt, is a great way to dress down a suit. Look for these at more progressive retailers.

The Pink or Red Subtle Patterned Shirt
Just fine for most. Beware though. For those with a super pale skin tone, pink might look a little flushed up against their easily sunburned skin. Opt instead for red micro-check or white.

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.