The Perfect Way to Wear Khaki Shorts (and Other Instagram Lessons)

Despite my intense seasonal bias toward high summer, I’m the first to admit you can’t beat end-of-May weather in New York. It’s right in the sweet spot between the post-winter stage wherein any ray of sunshine feels like an unprecedented novelty and fry-an-egg-on-the-sidewalk hot. It’s pretty much perfect — if I may be so bold as to pronounce it such — and therefore makes for pretty much perfect corresponding outfit opportunities. Scroll down for five bits of inspiration I’ve saved in my Instagram bookmarks folder for this precise purpose.

As documented in my 500-word essay about how enamored I am with Jackie O.’s vacation style, I love a good silk headscarf. They remind me of my grandmother, who wears silk scarves around her hair with big sunglasses and red lipstick. It’s instantly glamorous in an old-fashioned kind of way. I like how Bettina injected some modern contrast by means of a colorful crop top, but one that maintains the outfit’s overall sophistication with its precise tailoring and boxy silhouette. Also, how good are these khakis? I’ve wished for a pair of khakis while getting dressed no fewer than three times this month, so I think I’m due for a purchase.

Doesn’t this outfit make you feel like you’re taking a nice, deep, yogic exhale? Or eating a spoonful of buttermilk sorbet? It’s so refreshing! And just the grounding perspective I need to take me into this warmer season, when my penchant is to dress myself like a fruit stand. Here’s proof that I can do the opposite and still say something exciting.

I have yet to master the knack of seamlessly pairing dresses with sneakers and making it look cool instead of childish, which is why I instantly saved this photo of Mecca to reference before my next attempt. I think the key, which she executes beautifully, is wearing a dress that errs on the side of sexy instead of cutesy. I also like how she layered a tie-dye top underneath. Need to copy immediately.

Oh how I love this Rejina Pyo dress, let me count the ways: 1) It looks comfortable enough to be a nightgown but fancy enough to wear to a cocktail party, 2) the subtle transparency reminds me of spun sugar, 3) it’s long-sleeved but not oppressive. I’m also very inspired by Naomi’s styling, which includes pink mules and a matching pink crossbody bag, leaning into the dress’ girl factor without going overly frilly or flowery.

Consider this my new favorite approach to wearing mid-thigh-length khaki shorts. There’s just enough skin showing through the shirt (which I’m obsessed with — PLEASE tell me if you know of a similar one lingering on the internet somewhere) that it counterbalances the dad-on-vacation connotations of the shorts.

What outfits have you saved recently? Drop some links below I’m eager for more.

Feature image via Naomi Shimada. 

Harling Ross

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

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