Our latest slideshow of street style, WeTransferred straight from Tokyo Fashion Week, reads like a page out of legendary editrix Diana Vreeland’s “Why Don’t You” column in midcentury Harper’s Bazaar. A few examples of Vreeland’s suggestions for the uninitiated or the unrefreshed: Why don’t you tie tulle black bows on your wrists? Why don’t you twist [your child’s] pigtails around her ears like macaroons? Why don’t you travel with a little raspberry-colored cashmere blanket to throw over yourself in hotels and trains? Why don’t you wear violet velvet mittens with everything? Why don’t you order Schiaparelli’s cellophane belt with your name and telephone number on it?

While extravagant beyond relatability and decadent to the point of absurdity, Vreeland’s column functioned as an early attempt at the “productivity hack,” and that’s what has always gripped me most about these ideas she tested and provided: I liked the way her questions forced me to step outside my own routine, reexamine the methods of problem-solving I’d been implementing, and to approach my wardrobe or the art of getting dressed from a different vantage point. I had the same reaction, though kindled through visuals rather than through writing, when leafing through this delivery of photos from Japan.

For these stale, lingering days of March, when style ruts abound, it’s high time for a 2019 round of Why Don’t Yous, courtesy of the style on the streets of Tokyo:

Why don’t you:

Wear the asymmetrical top at the back of your closet as a vest (1)?
Reassess your popcorn shirt from the ’90s (3)?
Wear a neon turtleneck under your blazer under your trench coat (4)?
Scavenge for a floral fleece and wear it with khakis (5)?
Buy a skirt suit but make it maxi (9)?
Match your scarf to your bag (11), especially if your bag is canvas?
Wear smudged lipstick across your face, but only if your friend will do it with you (14)?
Wear orange eyeshadow if you have pink hair (24)?
Craft croakies beaded with the palette of Ugo Rondinone’s Seven Magic Mountains (26)?
Make it a personal mission to look for the biggest sequin you can find (31)?
Consider a pair of lavender pants (32)?
Keep your grazing skirt from getting dirty with a pair of platform sneakers (37)?
Wear shorts under a paisley robe (39) and proceed as usual?
Pair python print with pastel corduroy (46)?
Entertain the possibility that you could wear a pair of orange vinyl board shorts (47), or a pair of clementine-colored tights (73)?
Sub out your office sweater with arm warmers (56)?
Wear a cropped tuxedo jacket with sequin bike shorts (60)?
Let your gold hardware speak for itself (80)?
Secure your pants with a tassel belt and a square knot (83)?
Scour TheRealReal for a Pleats Please set (84)?
Exceed expectations at a job interview and wear not one tie, but two (97), or one tie at giraffe-scale (108)?

If you need me, I’ll be dreaming of that aquarium-adjacent skirt where a school of fish take residence in slide 73.

Photos by Matthew Sperzel @sperzphoto.

Man Repeller editors endorse products we genuinely love. If you end up buying something through our links, we may earn an affiliate commission. Learn more here.

Get more Fashion ?