I’ve Been Window-Shopping for a Nonexistent Fall Vacay—Here’s What I’d Pack

Now inching closer to the tail end of summer, I’m sad to report that I’ve gone vacation-less all season. At the start of April, I had envisioned running off to a tropical getaway, but like most things, it’s easier said than done. Instead, I’ve been watching others bask at the sunny beaches of Tulum and swim near the picturesque coastlines of Portofino via my IG feed. It may seem a bit glum, but watching others’ glorious vacations has inspired me to finally actively plan for my own. And of course, a major element to the fun of running off to an exotic destination is the preparations; it’s one of the few times where being extra is essentially a requirement (so you can think about leaving your most practical basics at home). In addition to bookmarking all of the places geotagged in my favorite tastemaker’s vacation snaps, the market editor in me has also been keeping tabs on all of the fashions. As I repeatedly scroll through Google Flights for deals and read through endless resort reviews, I’m outlining all of the outfits I’ve mentally “packed” so far. If you too plan on visiting somewhere nice within the next few months, consider this your guide to mastering early fall vacation style. Keep scrolling to see the outfit inspiration on my mood board, in addition to looks for every travel scenario.

One of the best parts of traveling is having no plans at all. No matter where I go I like to leave enough time to aimlessly wander through small side streets and quirky gift shops to find hidden gems. In situations like this, it’s best to go with pieces that are versatile enough to work across all environments—whether that be a nice restaurant or a trip to the park. A cool oversized shirt and patterned jeans strike the balance of fun and comfortable. Last but not least, flat shoes are a must.

Welcome to the fashion person way of hitting the beach. In my case not just any coverup will do—right now I’m completely enthralled by Louisa Ballou’s elevated printed sheer dresses and swimsuits. To top off the drama: magenta sunglasses and a unique green woven tote to hold all of the trashy beach reads.

The chronically overprepared may already have dinner reservations lined up, but more often than not my travel buddies like to be spontaneous about our eating plans. A matching skirt set is a no-brainer that fits within every dining atmosphere. Another plus: the knit material makes this very easy to pack.

Reserve your Sunday best for browsing beautiful works of art and captivating exhibitions. These plisse pants look way more expensive than they are and are so comfy you won’t mind spending hours walking through every exhibit.

A vacation is the best time to deviate from the norm. Whether it’s grabbing drinks with a new acquaintance or spending a night out on the town, you’ll need a look that ensures all eyes on you.

Sure, you’ll be sitting in taxis, planes, and trains all day, but you can still look chic doing it. My go-to is a long-sleeve tee (for all of the excessive A/C) and a sweater of some sort for extra warmth. An oversized knit vest and classic high waist sweatpants is truly a failsafe option. Don’t forget a roomy tote to shove in all of your essentials and any last minute packing remnants.