Plaid shirts used to strike me as too tomboyish and style-less, but now I like them a great deal, and am—since I only have one—looking to expand my repertoire. I like how they look all oversized and slouchy, like here, and though they’re a natural with jeans, they get about a hundred times chicer when you pair them with trousers (I especially like how they look with leather pants).

The color really pops against the grey here.

And I adore black and yellow together wherever I find it.

The contrasting pockets and cuffs here are fun.

I like that this one is kind of faded out.

Blue on blue is always a winner in my book.

This silk option is nicely refined.

This is just pretty adorable.

Here is one I might go for: the blue and red together is so strong.

From Frank & Eileen, a shirt brand I really like: blue and white and nicely graphic.

I am mad for the poppy color combination here.

Here’s a sweet, feminine choice.

Red and black always looks great.

And finally: a classic scotch plaid from LL Bean.