Finally, the time has come. Memorial Day weekend is here and, with it, the real-deal start of summer. And none too soon. We need this. Game Of Thrones is a wrap. The album of the season is here and on a loop in the office – thank you, Mr Mark Ronson. Our abs are stacked and we’re ready to get a little lost.

Because we’ve thought about little else for the past few weeks, we talked to a few of the most stylish guys around to hear what they are getting up to, where they are headed and, most importantly, what they are planning to wear. What better way to get some weekend inspiration?

“I’ll head to the small town of Sandisfield in the Berkshires. Four years ago, I bought a 1923 hunting cabin there and have been attempting to turn it into a year-round compound. I originally bought the place thinking it would be a quiet retreat for writing. As it turns out, I write much better in the city (although a surprising number of writers I admire called the Berkshires home: not just Herman Melville and Edith Wharton, but Norman Mailer, Pauline Kael, and Patricia Highsmith started writing The Talented Mr Ripley over a summer in a cottage in Lenox). I have just enough friends around that I don’t turn completely feral in the woods. What’s great about Memorial Day weekend is that it officially ends what is known in the Berkshires as ‘mud season’ (that’s spring to the rest of you). The mud finally dries to dirt, grass turns green and summer can begin.

“If it’s warm enough, I’ll go for a swim in Spectacle Pond, which is the lake near my house. Tanglewood is up here, it’s a music venue that hosts the Boston Symphony Orchestra for the summer, along with some other great acts (I saw Bob Dylan play two summers ago). My own version of Tanglewood at Thurtilperk Hill (the name of my house, which predates me) usually involves spreading a blanket out on my meadow at sunset, blasting some classical music and drinking wine. I’ll probably attend a few friends’ barbecues, and there’s always a drive into Great Barrington for supplies and a trip to the used bookstore, Yellow House Books.

“When I first bought the house, I was so afraid of ticks and Lyme disease that I wore all white, all the time. I mean, I must have looked like a cult leader when delivery people had to drive a mile down my mud driveway to see me exit a cabin in bright, bleached solar white from head to toe. Luckily, I’ve chilled out on that fear (there are so many black bears in the area, my fear has gone from micro to macro). It’s the country. But I am unveiling a special new drink I discovered last month in Bolzano, Italy: a Cynar spritz. Cynar is an amaro made of artichoke, and you mix it with club soda, prosecco and lemon, and there you have it, my new summer drink. Credit me when you try it on your friends.

“In terms of tips, I only have two. First, always always keep a paperback novel around. We aren’t constant entertainment machines for each other. Being able to enjoy time alone, paradoxically, ensures you will always be invited back. If you’re a guest at someone’s house, you need to disappear for a little while to let the host have their own time. If you’re a host, sometimes you need a break from all the socialising and entertaining, to just read in a corner or under the trees. Paperback novels will save friendships over long weekend visits. Buy them and use them liberally. Second, clean up your trash immediately. You will only drink more and be less motivated in an hour and if you don’t clean the dishes right away, a black bear will be happy to lick them clean for you. Plus, no matter how rotten you feel the next day, you’ll at least take heart in the fact that you were mature enough to clean the kitchen.”

“I’m going to a wedding in Boothbay Harbor, Maine, which is about an hour from Portland. I’ve only been to Maine once, in January (huge mistake: the weather), and made a pilgrimage to the gigantic Bean Boot outside the LL Bean factory store in Portland, so I’ve always kind of admired the outdoor-prep thing they have going on up there. In the summer, though, I imagine the dominant vibe is more of a Lilly Pulitzer or Wasp-type energy. Speaking of which, the bride, who is a friend from college, cried when Lilly died. It’s going to be a hell of a wedding. It’s black tie, obviously, which is a strong move considering it’s the first nuptials most of my friends from school are attending, myself included. I don’t get invited to enough fancy events in New York, so I’m looking forward to breaking out my double-breasted Drake’s tuxedo. I hope the groom’s tux has sequins or something. For footwear, I’ve been dying to wear my vintage black lizard cowboy boots with my tux. The groom’s family is from Texas, which feels like a green light. But I’ll pack a pair of smart shoes, too. Just in case.

“The wedding day dress code also calls for ‘festive bow ties’. If I have a hard-and-fast style rule, it’s that I never wear ‘festive’ neckwear. I’m going to bring a vintage Hermès bow tie that has a cool black-and-white Art Deco print, just in case literally everyone else rocks up in critter bow ties, but I’m 99 per cent sure I’ll wear the grosgrain Drake’s one that matches my tux.

“The rest of the wedding is smart-casual, which, to me, means Our Legacy silk shirts, chinos and Gucci loafers. I’m hoping to play some tennis while I’m up there, but if we’re being honest, I’ll be hungover by the pool wearing a swimsuit with a pair of Jacques Marie Mage shades attached to my face. If I have one piece of Memorial Day-weekend packing advice, it’s this: bring a sweater. It isn’t actually summer yet. I like the linen-blend ones by Jacquemus.

“I’m flying up to Maine. Usually, if I have to travel with a suit, I just wear it on the plane. So I guess I’ll try to fit my garment-bagged tux in the largest tote I can find, and stuff everything else in my Rimowa.”

“One of my favorite things about living in Los Angeles is that I can throw stuff in my trunk, get in my car, drive for two hours and end up on another planet. The first time I ever visited Joshua Tree, I couldn’t believe we were still on Earth. I’ve stayed all over the area – in super cheap motels, at the Joshua Tree Inn, Airstream trailers, the Parker, many Airbnbs. The best, though, is backcountry camping in the park, falling asleep under meteor showers.

“The most important things to bring are my bike — a carbon-fibre Colnago — and my camera, a 35mm Leica M7. The rest: Master-Piece hiking backpack, rubber Birkenstocks, lots of sunscreen and moisturiser, my Jacques Marie Mage Taos sunglasses, Orlebar Brown swim trunks (my pair is actually custom; it has a photograph I took of Joshua Tree on it). It’s pretty much hiking-type clothes the whole time: drawstring shorts and T-shirts and hoodies, and a gilet if it gets cold. In the mornings, I usually drive out to Palm Desert to do an early bikram class before heading into the park. If it’s a biking day, then it’s Assos and Rapha – that whole Lycra deal. Long bike rides through the park are a fave. Late afternoon, I’m back in shorts and tees, or sweatpants and a jacket if it’s cool at night.

“The Cholla Cactus Garden is one of my favourite spots on the planet. I’m trying to see if I can get my ashes spread there. I like it in the day, but it’s the best right as the sun goes down. I love the sound baths at the Integratron, the gigantic rock in Landers; the Noah Purifoy outdoor museum; my friend Steve’s place called The Station; the rock climber’s cookie at The Natural Sisters Café… Always make sure you have enough gas, water, food and clothing with you. The only way to do a loop through the park on your own (and not die) is to go the night before and stash water at the ride’s halfway point. The desert is magical, but can also be scary. That’s part of what makes it feel so special.”

“I have a house on Fire Island that I share with a friend. It has been in our extended gay family for about 12 years. It has gone down from eight people sharing it for a summer, to six, to four people, and now there’s just two of us. It’s a shack right on the ocean.

“I always start the morning off with coffee on the deck overlooking the ocean and then, at some point, meditate. I like to get up super early. There might be some stragglers still out from the night before, but no one really bothers you. We are 10ft from nature. And to be two and a half hours outside of the city, and being transported into this summer camp… It’s everything. June, July and August are the three most special months of the year for me.

“One of the beauties of Fire Island – a blessing and a curse – is that there’s literally nothing to do. There’s a central business district that has two bars, three shops, one grocery store, one liquor store, a pizza place and that’s about it. We make a daily trek to the grocery store like it is something to do. Basically, I’m just at the house or on the beach. And everything you’ve heard about it is true, but at the same time it’s a nature preserve that we shouldn’t be on. They’d never allow this to be built now. You have to see it to believe it; Fire Island is really one of the most extraordinary places on the planet, as far as I’m concerned.

“I go there all summer, every summer, so I do leave things there. I have six vacuum-packed bags full of clothes. I keep a wardrobe there that any two normal people would find adequate. Still, I bring more stuff every weekend. Memorial Day weekend is kind of like the triple crown of packing because it will still be freezing, so you'll be in beach sweaters, lots of cashmere. I have shorts in every shade of khaki and brights and pastel as well. I am big on shorts and a sweater. Fire Island is tailor-made for The Elder Statesman. My go-tos are cashmere tie-dye, in all three weights – the heavyweight, the medium weight and the tissue weight. Then, the Rick Owens cashmere will come out. That’s one thing that I don’t leave. (They’re good for the plane, too.) A heavy cotton fisherman’s sweater, Ralph Lauren cotton sweaters. And then hoodies – it’s the season of the hoodie – vintage college hoodies.

“I love Rick Owens Birkenstocks, but I’ve always turned my nose up at flip-flops. The gateway shoes for me into the world of open toe were the Hender Scheme Teva, and the rubbery, one-piece Birkenstocks. You could basically hose them down. I’ve been rocking that for the past two years with a Nonnative Gore-Tex jacket that I got in Japan. My allegiance is with James Perse T-shirts – they’re so well made.”

“I am staying at a new hotel in the town of Tulum called Casa Pueblo. Staying in town allows me to have the perfect environment for work, play and pleasure. I remember my first trip down to Tulum, about six years go. There was this sense of being secluded – a very different environment of my normal day to day life here in New York City. I’m always looking forward to exploring places that are a bit off the beaten path. Every trip down there I’m witnessing the progression of the what the city has to offer; whether it’s a new restaurant, or a new jungle-side road that is opening up.

“Packing light is key. Nothing more than a carry-on. My look in Tulum is a bit more minimalist than my traditional vacation attire. I tend to pack products that are multi-functional and a bit more neutral, whether it’s the classic Onia hybrid shorts that function as a swim suit, or a clean, white linen button-up shirt that I can wear to the beach and a dinner at night.”

“I’m going ‘home’ for Memorial Day weekend. I’m from Northern Virginia and I lived in Washington DC for a while before moving to New York. The city’s gone through an incredible transformation. I worked with Erik Bruner-Yang at a sushi restaurant called Sticky Rice a long time ago, and now he’s an award-winning chef and overseeing so many cool projects in DC, from The Line hotel to Maketto.

“This weekend, I’m attending a wedding with my girlfriend, but we’ll most likely spend some extra time catching up with my family and friends down there. The city is a world away from the suburbs, and it’s always interesting to see that contrast driving down the highway.

“In DC, I always do the rounds visiting some of my old haunts, such as Commonwealth, Smash! and Ben’s Chili Bowl. If I’m seeing old friends, we might end up at Policy or Rosebar. Usually I’ll make time to grab at least one cheeky lunch at Nando’s. It’s the only city in the US I can ever eat it! I also try check out some new spots each time. The food scene has gotten exponentially larger and more diverse, and it seems whenever I come visit there are always two or three new spots with a lot of buzz.

“I’m bringing a tuxedo with me for the wedding. Transitional weather is tough, but I’ve got a Prada mohair and wool-blend tux that should be fine. Needles sweatpants have become my go-to travel trousers. They’re really comfortable. I always wanted a black pair with royal blue stripes and finally tracked down a pair. They’re a collaboration with textile designer Masako Noguchi.

“If I’m seeing family, I tend to dress more low-key in pieces where God is in the details – things that aren’t too fussy when I’m with my nieces and nephews. They’re at the age where they’re starting to pay attention to sneakers and streetwear so I still have to come correct. I have a Stone Island ripstop overshirt I can’t stop wearing, Sies Marjan corduroy trousers, Noah military herringbone chinos, Our Legacy moleskin khakis, and a Maison Margiela crew-neck sweater I’ll usually bring, along with a ton of graphic tees. I’ll also probably pack a pair or two of Patagonia Baggies shorts, both for running and swimming.

“I try to limit myself to three pairs of shoes. I used to go way overboard but I’m better now. My current go-tos are Gucci Horsebit loafers with a lug sole, Prada Cloudbusts, and the blue-toe Union x Air Jordan 1s.

“Packing cubes have changed my life. I have three from this brand Millican that really maximise what I can stuff into my Rimowa carry-on. My wash bag is pretty light – I use a neoprene Porter-Yoshida & Co one that Highsnobiety collaborated on. I usually pack a toothbrush, toothpaste, my current cologne, some moisturiser, deodorant, and Aesop hand cream.

“The biggest lesson I’ve learnt from travelling so much is the importance of packing right. Usually that means packing a lot lighter than you think. It takes a lot of the guesswork out of getting ready and you can focus more on the ‘vacation’ part of the equation.”