“More tomboy please!” writes a commenter named Lisa, rather succinctly, and the pleasure is all mine: this is how I dress most days, and especially now that the whole world has gone casual. I’d say a striped tee is a perfect starting point, and this one from Kule is pretty ideal. Here’s another one I like that’s cheaper.
And here’s a good long-sleeved striped tee from Saint James that comes in several good colorways.
You can’t beat a classic white button down, and this one is nice and lightweight.
I really like their utility jumpsuit too, in this good slate-y gray.
A pair of jeans that isn’t too tight, but also isn’t so loose that it’s sloppy is a good way to go. I like this straight-legged pair from Madewell.
For some reason, I have convinced myself that hoodies are sexy, which may or may not be true. But they are the ultimate in easy tomboy style, and so good for layering. This cashmere specimen is a good weight for the weather we’re having right now in New York.
A navy blazer is just a little more gamine and French than a black one, and is also a super-easy way to incorporate at least a little color into your outfit.
And of course, a good chore jacket is a really simple way to channel tomboy style. I think the dusty rose hue of this one is kind of nicely unexpected.
As far as handbags go, the simpler the better. I like Clare V’s Sac Bretelle because it is perfectly unadorned and fits more than it looks like it will.
I like a flat mule for kicking around, and this one is currently marked down.
Of course, any good tomboy has at least one pair of well-worn sneakers, and I like these from Puma because of the nice big platform.
If you really want to do the look in a head-to-toe way—like, literally—you might want to consider a fisherman cap, which looks cute on pretty much everyone.
And finally: a delicate necklace adds just a touch of femininity. I lust for this antler pendant from James Colarusso.