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3 Genuinely Useful Transitional Outfit Hacks
05.28.19

In partnership with THE OUTNET.

At the boarding school I attended from ninth through twelfth grade, the term “dirty dinner” was commonly deployed to describe the act of going straight from after-school athletic endeavors to dinner in the dining hall without showering in between (in other words, still wearing the same clothes you wore during sports practice). I was a frequent practitioner of dirty dinners, partially because I was a hungry teen and too lazy to change, but also because I had yet to master the art of transitional dressing.

Transitional dressing, a.k.a. dressing in a way that lends itself to modification depending on the situation at hand, was a skill I didn’t master until adulthood. It’s inherently tricky, because it requires thinking multiple steps ahead. I personally find it hard enough to come up with one aesthetically-pleasing outfit in the morning, let alone two that also take into account the practical concerns of a day that starts out one way and ends another. However, there are a few tricks that have proven useful time and time again. Scroll down to see how I tackle three common transitional dressing scenarios using clothes and accessories from THE OUTNET.

From Ticking To-Dos to Twirling Pasta

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I often tick through my weekend to-do list on Saturday afternoons, which means I’m running around doing everything from grocery shopping to picking up dry-cleaning to returning the too-small shirt I bought online, and by the time I’m finished it’s already 6:00 p.m. I used to decline social invitations that cropped up at this hour because I thought I needed to go home and do a full outfit change out of my comfy, easy-to-move-in errand clothes and into my thoughtful, night-on-the-town weekend dinner clothes, but I’ve learned to take a more creative approach.

That approach starts with a tailored pair of shorts, an obvious daywear item that is significantly underrated when it comes to eveningwear. Shorts are the rare lower-body garment that look good with both sneakers and high heels, which makes them perfect for running errands that bleed into dinner. For daytime, I like to pair them with a colorful button-down with rolled-up sleeves worn over a plain white T-shirt. At night, I’ll remove the T-shirt and roll down the sleeves for a more polished look. Fortunately for us all, satin mini bags are appropriate 24/7.

From Sweats to Shivers

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Whether grappling with the prospect of a hot day turning into a chilly evening or a steamy commute turning into an AC-blasted office, temperature oscillation can be one of the most challenging obstacles in getting dressed. My go-to hack for this is the ’ol pants-over-dress maneuver, with the addition of a blazer for arm goosebump prevention. A silk scarf can work wonders in this scenario as well, transitioning from a headscarf that keeps your hair off your neck in the heat to a neck scarf that keeps your throat toasty in the cold. Office AC really overdoing it? Add a pair of socks for extra foot insulation.

From Goodnight Moon to Good Morning Croissant

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When I was little, I would frequently sleep over at my best friend’s house because she lived a mere two blocks away. I would wear my favorite pajamas when I walked over there at night, as 12-year-olds are wont to do, and throw a fleece or sweater over them when we went out to grab bagels the next morning.

My suggested approach to adult sleepovers, whether at a friend’s or partner’s, is not entirely dissimilar. I recommend wearing glorified pajamas, whether that’s silk pants and a camisole or a slip, and then bringing along something to layer over it for a more morning-appropriate look the next day. A big, cozy sweater or light jacket are great options. As for shoes, why not lean in and wear a pair that could moonlight as slippers? Sunglasses optional but encouraged if you want to look like a cool celebrity leaving the home of a secret paramour.

What transitional dressing hacks do you have up your own sleeves? Tell me in the comments.

Photos by Edith Young. Makeup by Celica Sea.

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