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5 Ways, 5 Days: Harling’s Pinstripe Shorts

There are few things more satisfying than buying a new article of clothing with the conviction that it will surely become a priceless closet staple. (“Staple” because it will go with everything in your closet and thus render the process of getting dressed easier than slurping down a buttery ramen noodle and “priceless” because it will be worn so many times that it will quickly pay itself back according to the cost-per-wear formula we frequently cite at Man Repeller.)

I was overcome with this exact breed of conviction when I scooped up a pair of pinstriped Totême shorts during Net-a-Porter’s summer sale a few weeks ago. I tried them on as soon as they arrived, and they fit like a g-dang dreamsicle. But as I admired myself in the mirror, I realized that for every classic wardrobe staple-esque attribute they had (perfect tailoring; suitable for any season; insanely cool menswear-inspired vibe), there was an opposing characteristic that rendered a contradictory effect (a length adjacent to but not quite in Bermuda; a dark color palette despite their summer-appropriate silhouette; pinstripes that would make Chuck Bass jealous).

So when Leandra asked if I would like to go next in MR’s 5 Days, 5 Ways series, I saw it as the perfect opportunity to light a fire under my pinstripe-wary backside. The shorts would finally fulfill their prolific outfit destiny…because I would finally have to figure out how to wear them.

Monday:

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Totême shorts — similar pinstripe shorts here, Stella Jean top — similar top hereRosantica earrings, Trademark bucket bag, Mykita sunglasses

To kick off the challenge, I paired the shorts with a top that makes me feel like the victim of a toilet paper prank gone so right. It’s an all-time favorite outfit addition and never fails to spice things up. But I was still in need of some extra seasoning: accessories. I proceeded to decorate the rest of my body with the fanatical precision of a kid with 15 minutes left at Dylan’s Candy Bar: pop rocks earrings, a green apple gum-ball of a bag and sour power strawberry banana slides. If you just started salivating, I’ll consider it a successful first day.

Tuesday:

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Dolce & Gabbana top — another black bustier here, Pucci scarf, Oscar de la Renta slippers, Roxanne Assoulin bracelets, Cutler and Gross sunglasses

I can’t believe it took me until Tuesday to realize that Carrie Bradshaw was also the proud owner of a pair of pinstripe shorts. I am, of course, referring to her outfit in the seventh episode of season four, in which she wears a pageboy hat and delightfully weird pinstripe knickers to clean up after Aidan’s annoying dog. I do not own a pageboy hat, but my tube top and head scarf were admittedly stolen straight from her aesthetic.

Wednesday:

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Chanel top, Rosantica earringsChloé sandals

I shepherded my shorts over the hump of Hump Day on a magic carpet ride of neon and feathers. Like a runny egg yolk or a funfetti grilled cheese, this outfit was made for Instagram. Recommended filter: Clarendon.

Thursday:

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Isabel Marant dress — another silk Hawaiian print dress here, Trademark slippers, Zan Zan sunglasses

On Thursday I realized it was almost Friday, which was exciting enough to render every shirt in my closet not exciting enough. It was time to shake things up. I dug through the back of my closet and pulled out an old Isabel Marant dress that I had purchased on sale from The Outnet right after graduating from college. I love this dress, but it’s one of those things that I don’t often have occasion to wear (because how often does one have the occasion to wear a glorified Hawaiian print handkerchief?) I put it on, unbuttoned the skirt portion, tucked it back and surveyed my handiwork. Day 4 was officially handled.

Friday:

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Flagpole Swim bikini top, Anna Sui kimono, Ancient Greek Sandals slides, Miu Miu sunglasses

I tossed all conventional rules out the window by the time Friday rolled around. Because why would I wear a shirt when I could wear a tiny sliver of water-ready fabric otherwise known as a bikini? That way, I could pretend I was at the beach squishing sand between my toes instead of at the office squishing tweets between my mouse clicks. To complete the look and protect my co-workers from the glare of my alabaster trapezoids, I covered up with a bohemian kimono for which Jessa from Girls would likely trade her painstakingly grown armpit hair. Vacation is a state of mind, you know? And so are wardrobe staples.

Photographed by Krista Anna Lewis.

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Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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