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How To Dress For An Entire Day Outside, From Park Hangs To Outdoor Dining

Chelsea Peng
·5 min read

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ICYMI, more of life is being lived outside than ever before. Six-feet-apart park hangs, tailgating out the back of your friend’s fuel-saving sedan, and long walks with a Boulevardier in a paper coffee cup — now that what’s left of our existences as social beings exists mainly through these sorts of activities, burning precious daylight (and pre-curfew hours, in some parts of the country) to make an outfit change mid-day just doesn’t seem worth it.

An all-day outfit therefore calls for an all-occasion — and all-weather — shoe, of which Converse has many, equipped with features such as chunky platform heels, insulated faux-fur linings, and premium leather. With these utilitarian-chic styles as a jumping-off point, we recruited three stylish R29ers to demonstrate the art of the 12-hour (or more) look, that can go from outdoor dining to impromptu bike ride to heat-lamp-ed patio with ease.

Ahead, we offer our best advice for dressing in an age when returning home to get ready — or even making a loafer-to-heel swap at your desk before heading out for the evening — has become largely obsolete. Because when the contexts and the time we can spend with others has been limited, clothes should never get in the way of us making the most of it while we still can.

Do You Even Layer, Bruh?

We have faith that you have your own personal order of operations when it comes to moisture-wicking tank top >> temperature-regulating base layer >> Display Shirt, but in recent months, we’ve reconsidered our own patented method, given that stopping to make an ensemble edit is less of an option when the sun sets basically right after lunch.

Here, associate social content strategist Venesa Coger avoids the midday outfit slump by layering a mixed-print turtleneck under a knit dress, with a rugby-inspired cardigan that can be removed and tied around her waist in warmer environs. And with a sock that subtly echoes the sweater and the pleats in her skirt (add lined tights for even more warmth) you have a cleverly thought-out ‘fit that’s as strong as the Chuck Taylor All Star GR82 she’s wearing. Bonus: the shoe has a durable, boot-like design and eye-catching straps for stomping around (securely).

Watch Your Tone

Building off our last point, when the fashion brief calls for wearing a larger quantity of clothes to keep your core temperature between a healthy 97 and 99 degrees, you want to build cohesion and intention in other visual ways. For software engineer Karina Carmona’s look, that tool is color: A Chuck Taylor Storm Boot paired with co-ords and a quilted jacket, all in a complementary beige, keep a texture-filled combination clean. And with the possibility of adding even more layers here — we’re thinking a second knit and leggings, for starters — just remember to keep it all in the (same color) family.

Game, Set, Match

In times of trouble, we turn to matching sets, mostly made out of fleece. And it makes sense: 1) There’s hardly any thought involved beyond locating the trousers; 2) There’s a certain level of put-together-ness in the obvious “these clothes were made to go together” way; and 3) They feel damn good to wear — anywhere. However, may we suggest a slight variation for 2020-going-on-“please let this be a better year?” As shown here on yours truly, a tracksuit in floral windbreaker fabric adds a heightened quotient of weather-proofing, especially when you throw in an extra-warm turtleneck, glorified long johns, and a wooly sock. Just supply your own outerwear should this winter not be balmy as it’s suggesting itself to be, and don’t forget the Run Star Hike, whose chunky platform and jagged rubber sole can traverse leafy sidewalks and artificial grass and curbside dining-room floors in high style.

Like what you see? How about some more R29 goodness, right here?