The Fall Travel Style Guide

The Finger Lakes are an underrated region for so many reasons. First of all, they’re one of the most beautiful places in the country. Second, they’re remote enough that they never get overcrowded. And, finally: it’s wine country. What more could you ask for? While all the lakes are lovely for different reasons, our pick for a long weekend this fall is Canandaigua.

Where to stay & what to do: 

Since traveling here is a little bit harder (more on that below), you might want to relax once you get here. And if that’s the case, we’ve got you covered. The Lake House on Canandaigua is one of the hottest hotels on the East Coast right now, and for good reason. It’s gorgeously designed and the staff places an emphasis on subtle hospitality, so you always feel taken care of. Lounge the day away at a poolside daybed, take on a more active experience by renting a boat and waterskiing, or indulge with a Finger Lakes wine tour–the hotel can set all of that up for you.  

How to get there: 

Though it’s not the quickest drive from the city (travel can take upwards of six hours if you choose to travel by car), heading to the Finger Lakes is simpler than you’d think—it costs under $200 to take a 75-minute flight to Rochester and then it’s a 45-minute drive from there. After a summer of sitting in Hamptons traffic or jostling our way towards a seat on the Montauk-bound LIRR train, we’ll take it.

What to wear: 

No matter what you do, keep it comfortable. The Finger Lakes are fairly casual–there’s more of an emphasis on activity than there is on style. During the day, pair a Hunza G one-piece with a pair of pleated trousers if you’re staying on land, and 90's style denim shorts if you’re on the lake. Don't forget to throw on our classic white hoodie to keep cozy for chilly nights by the water. 

In 2020, a number of lifelong New Yorkers said goodbye to the city in favor of (literal) greener pastures in Hudson Valley and the Catskills. And while lots of the spots have since become a bit cliched, there are still a few spaces that feel sacred. One of them? The Dutchess, a “secret” hotel and farm-to-table restaurant in Hudson Valley. We can’t share too much about it (the air of mystery is part of what makes it special, after all), but we will say: everything is organic, hyperlocal, and communal, so you’re going to want to eat every meal here. They’ll also arrange your activities–from yoga to meditation to hikes–but you’ll need to email them to get any information whatsoever, and that’s part of the fun. 

 What to wear: 

As with the Finger Lakes, Hudson Valley is quite casual, but you can have a little bit more fun. Wear our crew neck tee, in any color, with a pair of denim overalls, and some suede sneakers, and you’ll fit right in. Add a pop of color and drape a polo sweater over your shoulders for chilly days. And don't forget your sunnies! We're loving all things acetate and this pair is the perfect finish to your look. 

It takes less than 3 hours to drive to Woodstock, and, once you’re there, it’s more than worth it. It’s at its best in the fall, offering up countless activities for all types of travelers, but we find it works particularly well for a girls' trip.

 Where to say and what to do:

The Woodstock Way offers several options, depending on your party size, but we recommend renting one of their residences, which are beautifully designed and still offer up access to the hotel lobby and shop. Start your day with a hike on one of the trails before popping by Mudclub for bagels, then spend the afternoon shopping. Finish your day with dinner at Silvia before heading to Early Terrible to finish up the night.

 What to wear: 

During the day, you can’t go wrong with a lounge suit–and why not match with the town’s gorgeous foliage in our apricot set? When it’s time to head out at night, pair our tailored vest with a pair of our embroidered straight-leg denim. Because what’s a trip to Woodstock without an homage to its iconic hippie sensibilities? Grab a pair of chic yet comfy running sneakers and your favorite tortoise shell sunglasses and you're ready to hit the road.