Which—as anyone who's ever fought the urge to shove the contents of her closet into her duffle can attest—is a taller order than it seems, especially when you need versatile attire that won't scream "tourist!"
Yes, it's possible to create a city-proof packing list that still fits in your weekender bag.
So, we put Instagram star (and road warrior) Kassala Holdsclaw to the test: Can you actually create a city-proof packing list that holds up for multi-block treks as well as late-night missions for turmeric-spiked cocktails—and still fit everything in your weekender bag?
With a genius assist from J.Crew, the answer is a resounding yes. Holdsclaw hit up the mega-brand's classic vacay wear with a twist (plus her own private collection) to curate a mic-drop travel wardrobe. Plus, she's sharing her best all-around travel tips—to pave the way for your next getaway.
Scroll down for a selection of gotta-have-it summer looks, plus a downloadable packing list of everything you need for a city retreat.
"I'm all for the spontaneous trips! Planning either the night before or morning of, finding somewhere not too far away by train or car," the Brooklyn-based blogger says of her usual city explorations, noting that she's recently hit up under-the-radar cool spots like Portland, Maine.
"The high-rise denim are my favorite kind of shorts for summer," she says of this weekend-trip essential. "They are so versatile and can be paired wth any color top—I would pair these with a colorful body suit and some slip-ons shoes, or even a cute small heel."
Speaking of colorful bodysuits, this fits-like-a-glove spaghetti strap version will legit go with everything in your closet, and takes up hardly any space in a suitcase. "I’m all for bodysuits that give you a comfy, easy look," Holdsclaw says. #Same.
"Stripes are all the rage this summer," Holdsclaw shares. "I have countless striped shirts in my closet. The best thing about this off-the-shoulder top is it can be paired with anything, and instantly make your outfit look classy." Her rec? Wear it with white denim skinny jeans for a dinner-ready look.
Shimmy into this fiery eye-turner, and you're basically an IRL version of the emoji Flamenco dancer—AKA ready to take on whatever the day or night brings your way.
"The best way I can fully feel immersed in a trip is turning off my phone," Holdsclaw says. "Even if it's sitting in the car or on a train, listen to music as loud as you can, have good conversation, look at your surroundings. Say yes to most things, lay in the grass, eat something new. Do things you wouldn't normally do!"
The one-and-done jeans, $125
Holdsclaw is a die-hard for cropped jeans—and this boot-cut pair is versatile enough to go with everything in your carry-on, so you're set for whatever adventure comes your way.
"Traveling helps me focus on experiences, the journey to new places, the beauty that surrounds me, including people," Holdsclaw says. "A lot of the time I tend to lose sight of things that actually matter to me on a day-to-day basis. [When traveling,] I can look back at the experience, the journey, the company I had and just smile."
Sensing a theme here? In Holdsclaw's book, only two solid denim pieces are necessary in the pants-department—the key is loading up on it-factor tops. "My closet is full of this french blue color," she says. "I love how this top can look dressy, but is still comfortable."
Holdsclaw manages to fit everything in a tote for the weekend, and rolls her clothes to take up less space. "Even though most of my trips are spontaneous, I make sure to make a list on my phone of everything I think I would need and then narrow it down while I'm actually packing."
Definitely on her list? This metallic linen tee, which does double duty as a daytime neutral and nighttime stunner—plus, it acts as a layering piece on chilly nights.
The catch-all clutch, $88
Need a finishing touch to your outfit that also doubles as storage for your keys and matcha packets? This summery gem delivers, and won't take up mega space in your luggage. So basically, you can focus on the experience instead.
You always need one bona fide secret weapon in your bag, in case the laid-back weekend you were imagining ends up calling for rooftop rosé. "You really can’t go wrong with an off-the-shoulder top this summer," Holdsclaw declares—and this jade green gem (which she advises pairing with boyfriend chinos) is a guaranteed route to all the festive vibes.
Now that you've got a primer on city-summer dressing at its best, click to download this complete, hyperlinked list (curated by Holdsclaw) for your next weekend away—it's a life-saver for last-minute packing.
Top photo: Keith Williams/@mountainbikekeith
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