I'm Long Overdue for a Vacation, so I'm Planning These Chic Looks to Cope

Sponsor Content Created With Guess


(Image credit: GUESS)

I can't tell you the last time I was on island time, sipping cocktails in the tropics surrounded by views so pretty they could be mistaken for a green screen. Based on those visuals, it's obvious that I'm desperately craving a vacation. This winter, I caught myself daydreaming about booking a one-way ticket from New York to anywhere with a beach and palm trees more times than I would like to admit. And clearly, I'm not the only one. Vacation dressing has been trending hard on Instagram lately, with celebs, influencers, and my fellow editors leaning in. As an optimist and shopping enthusiast, I'm dutifully using fashion as my manifestation tool by planning endless vacation-ready looks. Do I have a trip booked right now? No. But if my friends are reading this, consider this your sign to drop some flight links in the group chat.

As of late, I've had my eye on all things floral, maxi, and colorful, and Guess's spring collection has all of the above and more. The pieces are light and airy, easy to style, and feel 100% vacation-ready. I'm already envisioning myself arriving at the resort with a bag (or two) filled with all of these shoes, accessories, and clothing items. Luckily, this coping mechanism benefits us all. I spent some time deep-diving into the Guess site and curating three full looks for your next trip. Even if you're not jet-setting anywhere soon, these looks are perfect for brunch, boat days, happy hours, and (quite literally) every other event under the sun. If you think you'll be able to contain your excitement and scroll through all of these chic finds, the ultimate warm-weather looks are ahead.

Hello, Happy Hour


(Image credit: GUESS)

When it comes to planning an outfit for happy hour, I always opt for pieces that spark joy. I mean, it's only right. If I'm stepping into a lively environment where the night may lead to dancing, a maxi dress is always my go-to, and this one has a subtle yet eye-catching print that spices up the look while maintaining that effortless vibe. I would elevate this casual number with dangly gold earrings and a straw hat to keep the look fun. The braided heels are the perfect day-to-night transitional shoe. Bonus points for the padding that makes them easy to walk and dance in.

Beachside Brunch


(Image credit: GUESS)

On the long list of things that I love, brunch has easily earned a top-five spot. I come for the food and stay for the impromptu photoshoot that ensues at the table while we wait for our order. An outfit like this one will have you feeling camera-ready and comfortable, and for that reason alone, it earns an A+ from me. The belted detail paired with the balloon sleeve feels ultra feminine, and the bucket bag adds the perfect spring-summer touch. You can't go wrong with a gold hoop earring and a classic pair of strappy sandals to tie the look together.

Set Sail


(Image credit: GUESS)

I can already feel the wind blowing through my hair and smell the salt water as I cruise through the ocean in this look. The pops of blue just scream boat day. When traveling, I love packing a matching set for easy dressing, and it would be a real shame if I didn't include some florals this time of year. The nude heels bring out the pink in the set and coordinate pretty perfectly with the shades, if I do say so myself. Pro tip: I'm a big fan of styling my matching sets as separates if I want to take my look from day to night without spending too much time getting ready.

Aniyah Morinia
Associate Branded Content Editor
Aniyah Morinia is an NYC-based associate beauty and fashion editor at Who What Wear. She has worked in fashion media since 2018 and joined WWW's branded content team, where she not only writes for some of her favorite brands but also creates content for them. Aniyah will find any excuse to get a photo of her outfit and absolutely loves taking photos. She graduated from the University of Florida in 2020 with a bachlor's degree in public relations and started post-grad life freelancing for EveryStylishGirl, Riot Swim, and Baby Tress. Since starting at Who What Wear, Aniyah has developed a passion for hosting livestreams, working red carpets, and creating TikToks in addition to writing fashion and beauty stories. When Aniyah's not writing or creating content, you can find her exploring Brooklyn and eating her way through the city. She'll never pass up the opportunity to uncover an NYC hidden gem or mix and mingle with her friends (all while swapping holy-grail products, of course).