Without looking like a walking chessboard, of course.
You can’t possibly go wrong with a pair of the Vans Checkerboard Slip-Ons that goes pretty much the entirety of anyone’s closet (except for maybe those embarrassing class t-shirts of eras past). Throw on a pair of these slip-ons over some ripped jeans and call it a day. Or, take cues from Steve Ellis’ effortless style:
Check this (pun intended, of course) fit from Supreme’s Spring/Summer 2016 drop: the reversible checkered MA-1 jacket. As seen on The Weeknd, you can opt to keep it low-key by keeping the checkered layer on the inside. Wanna go all-out? Flip the switch and wear the jacket with its checkered side out. But make sure to keep the rest of your look simple with basic colors and most of all, put on a cheery smile – because the world doesn’t need to know that you’re weeping on the inside from blowing cash on the fit.
If you want to invest in statement pieces, bags are the way to go. Just look at Fabolous stunting with his checkered backpack from Louis Vuittion. Checkered prints also look sleek in black and gray. Another color option can be seen on Bieber below, who seems to be multi-purposing his bag as a shield against rabid paps.
Switch things up a little by going for tartan instead. The recent Supreme x Comme Des Garcon SHIRT collaboration includes the perfect fits featuring tartan-esque patterns to experiment with. If you’re worried about how you look, take a leaf out of Sarah Snyder’s book, i..e, make the look work for you.
If all else fails, pop on a cap and call it a day. Or try a checkered hat too, if you wish. Peep these options from Golf Wang and Stussy.