Founder, Nasty Gal

What are your summer travel plans?
I couldn't be more excited. My boyfriend and I, along with our Parti-Poodle, Donna Summer, are heading to Santorini for five days and Paris for another five. A poodle in Paris! So perfect. We've booked an apartment in the Marais with a little balcony—so sweet.

When is the best time for you to get away?
I love getting away around New Year's, after learning my lesson the hard way that there truly is no work for me to do around that time. My attorneys, board members, etc., are all smart enough to go away, so I have begun to as well.

Where do you like to stay?
I love staying in boutique hotels. I really abhor giant family-packed resorts. If I'm on the beach, I want to be on the beach. I'm not into high-rise buildings above a beach. Miami, however, may be an exception. I'm a fan of the Aman resorts and anywhere that's warm. I generally avoid the cold!

Three favorite things to do while you're there?
I love to explore the spa! Massages are a must. I also love exploring a place through its cuisine. So I'll research to all-hell the best restaurants in town and make sure I get an early reservation. And, last but not least, I like to sleep! Ah, the great indoors. R&R is A-OK with me.

Best things to eat and drink there?
Oysters, wine, and bread.

Who do you go with?
Friends. My boyfriend and I get away plenty together and love to bring our friends. There's nothing better than taking my favorite people in the world along with me for incredible adventures.

What will you be wearing?
I wear flats so much more when I travel!

One thing you absolutely have to bring? One thing you leave behind?
I'm a magazine junkie. I make a stop at Hudson News and get buck-wild every time. There is no magazine too smart or too dumb—I pile the Harvard Business Review on top of Us Weekly and prepare for impact. I also MUST bring a steamer! I leave behind as much of my stress as possible. Always.

Photo: Courtesy of Sophia Amoruso

Cofounder, Acne Studios

What are your summer travel plans?
This summer I will travel to Biarritz in southern France, spend time at my summerhouse in Torö in the Stockholm archipelago, and visit New York.

When is the best time for you to get away?
The best times workwise are breaks in between seasons. If I could choose freely, I would say the best time to get away would be during the winter season as it is so cold in Sweden.

Where do you like to stay?
I really love staying at hotels, and prefer that to renting a house or an apartment. The Carlyle in New York is one of my favorite hotels—in my opinion, it epitomizes old, classic New York.

Three favorite things to do while you're there?
I like to play basketball on the Lower East Side; I always encourage my friends and family to join. I also visit bookstores and look for vintage furniture.

Best things to eat and drink there?
Katz's Deli is a favorite, and I often get a coffee at The Smile.

Who do you go with?
I often visit for work but also go with family or friends.

What will you be wearing?
I plan to wear a T-shirt, suit, and sneakers. One of my favorite things about New York is that there's no dress code.

One thing you absolutely have to bring?
Minimum one pair of shoes for each day I travel. I hate to wear the same pair twice.

One thing you leave behind?
Dear old Stockholm.

Photo: Courtesy of Jonny Johansson

Creative Director, Coach

What are your summer travel plans?
I still need to arrange this year—but considering Machu Picchu. I like the idea of getting some exercise in over the summer, too.

When is the best time for you to get away?
I really love to take time off for Christmas and New Year. It's usually fairly quiet workwise, and I love all the activities around that time of year—cooking, winter walks, but especially presents.

Where do you like to stay?
I think my favorite-all-time trips have been in the U.S. I love Amtrak trains, where you can travel huge distances and sleep in a cabin. You see amazing scenes from the windows and can stop at some really cool, unexpected places. I have traveled north, south, east, west, all over. I didn't know at the time, but it's now helpful as I'm referencing the trips in my work.

Three favorite things to do while you're there?
Explore, sleep in, and swim.

Best things to eat and drink there?
I don't generally cook, so I like to have a go when I have time off—to varying success. I can follow a recipe, but my problem is that I can be way too ambitious.

Who do you go with?
Friends, family, lover.

What will you be wearing?
It's great to be relaxed and not worry about how everything is put together for a change. But it's also fun to dress up for a special night. I like the feeling you have when you go for a night out after you've had a day at the beach.

One thing you absolutely have to bring?
A beautiful leather travel bag. I find it sets the tone and makes you feel good even when you're at your most casual.

One thing you leave behind?
As much as possible. I'm actually pretty good at traveling really light. One bag for two weeks!

Photo: Courtesy of Stuart Vevers

Designer, Isabel Marant

What are your summer travel plans?
Formentera and Ibiza

When is the best time for you to get away?
August is the only time possible with my very busy schedule.

Where do you like to stay?
I always rent a house. I like to cook and invite a lot of friends.

Three favorite things to do while you're there?
Swim, read, rest!

Best things to eat and drink there?
Rosé and jamon iberico.

Who do you go with?
My husband, my son, and some friends.

What will you be wearing?
Shorts, T-shirts, and bathing suits.

One thing you absolutely have to bring? One thing you leave behind?
I absolutely need to bring my music and books and my Mariage Frères tea. I leave my work behind!

Photo: Courtesy of Isabel Marant

Artistic Director, Diesel

What are your summer travel plans?
This summer I'm planning to go to Tulum; Ubud, Bali; Marrakech; and Kauai, Hawaii.

When is the best time for you to get away?
That's always so difficult! I will try to find a few days here and there when I'm not working…I will try to take a few weeks off in August.

Where do you like to stay?
I'm easy, depending on where we are going. Love to stay in a small beach house in Tulum. I want to try Riad Madani in Marrakech, Amandari in Ubud, and rent a villa in north Kauai.

Three favorite things to do while you're there?
Read, read, and read!

Best things to eat and drink there?
Fruits and coconut juices.

Who do you go with?
Tank and Bambi (my dogs).

What will you be wearing?
Shorts.

One thing you absolutely have to bring? One thing you leave behind?
Bring: Toys for my dogs. Leave: My Mac.

Photo: Courtesy of Nicola Formichetti

Model

When is the best time for you to get away?
The best time to go away is August, right before fashion week begins.

Where do you like to stay?
With my family when in London and Jamaica.

Three favorite things to do while you're there?
When I am in Jamaica, it is all about family, food, and the beach. I have extended family in Jamaica, so I spend a lot of time with them.

Best things to eat and drink there?
In Jamaica, it's all about the jerk chicken and the exotic fruits. When in London, it's my mom's home cooking.

Who do you go with?
With my brothers and mom or by myself. This summer I will take my son, Riley.

What will you be wearing?
I like to be casual when in Jamaica and at festivals. I love Lisa Maria Fernandez swimsuits, Illesteva sunglasses, and Sophie Webb sandals. When I go to festivals, I like simple dresses from Reformation.

One thing you absolutely have to bring? One thing you leave behind?
Maybelline's Volum' Express The Colossal Waterproof Mascara is a must, and leave behind any eyeshadows or blushes.

Photo: Courtesy of Jourdan Dunn

Founder, The Man Repeller

What are your summer travel plans?
I'll be in New York, and then in August I'm spending a week in Croatia.

When is the best time for you to get away?
I think always and never are both pretty accurate time periods, so I just take the trips as the plans start budding.

Where do you like to stay? And what are your three favorite things to do there?
Most recently, my husband and I stayed in a small bungalow in St. Barts last March, which was wonderful because we got to cook (make cereal), travel to different beaches, take hikes. I really like a vacation that forces you out of your comfort zone.

What are your top tips for eating/going out there?
Don't think about what you're eating, just eat. And does drinking wine out of the bottle on a beach count as going out?

Who is your favorite traveling partner?
Tie between my husband, Abie, and my friend Elyse, who is always DTD (down to dance).

What will you be wearing?
An off-the-shoulder, tent-style white linen blouse with ruffle detailing at the sleeves and collar and a makeshift sarong—no shoes, lots of gold necklaces. I may have been a pirate in another life.

One thing you absolutely have to bring? One thing you leave behind?
Bring your A-game, leave your dignity? Just kidding.

Photo: Courtesy of Leandra Medine

Founder, VFiles

What are your summer travel plans?
At some point I have to go to Australia to renew my visa—not the plastic kind!—and I will be spending tons of time in the Hamptons at our VFiles pop-up shop and at SoulCycle out there. If I'm really lucky, perhaps I'll get to visit our VFiles Sport Plus collab with Harvey Nichols in London.

When is the best time for you to get away?
It's always hard to get away; there's never a good time with family and a startup, so the key is to make day-to-day things more "summery." We have a yellow bench outside the store and I'm planning on sitting on it a lot more this summer!

Where do you like to stay?
If I get home to Australia, my favorite place would be our cabin on the beach on the Victorian coast.

Three favorite things to do while you're there?
See my family, family, family.

Best things to eat and drink there?
OK, ready…Tim Tams, Lamingtons, lemon slice, sausage rolls, a couple of party pies, maybe a Wagon Wheel, my mum's roast, and my dad's satay. Melbourne tap water is literally the best water in the world.

Who do you go with?
Hopefully someone from my crazy-busy family!

What will you be wearing?
For the plane trip, I 100 percent change into the Qantas pajamas—they are so comfortable, I end up living in them—and then multiple pairs of skate shoes (Givenchy, Louboutin, Nike, Keds), every HBA hoodie I own, vintage accessories, Sam MC T-shirts, VFiles Sport Plus basics, a litany of leggings from SoulCycle, and my new obsession, Nasir Mazhar.

One thing you absolutely have to bring? One thing you leave behind?
I have to bring my Kindle. One time I forgot it and I had to buy one out of the Best Buy vending machine at JFK. I cannot do over twenty hours of traveling without it. And the one thing I leave behind—actually, four of them—are my four dogs, Henry, Willy, Dottie, and the Tedster.

Photo: Courtesy of Julie Ann Quay