14 Fashion Tips from the Hamptons’ Most Stylish

by Eddie Roche

Some of the chicest dressers in the world spend time on the East End each summer. Our annual list celebrates the women and men who aren’t afraid to pack an extra suitcase (or three) every season. We’ve asked a few of this year’s style winners to tell us how they do it! 

1.Sunny Hostin, Host The View and author. 

Sunny Hostin

Personal Style Philosophy: “My personal style approach is elegant and chic—clean lines with just a bit of bohemian. Our stylist on The View, Fran Taylor, knows my style, but will also help push me out of my comfort zone. I tend to like things that are tailored with just a pop of color—orange, burnt gold, and moss green. I also love a fun accessory—a piece of tortoise jewelry or my Samira 13 Jewelry sunburst necklace, which I practically never take off!”

Favorite Brands: “I love Sergio Hudson and Ulla Johnson. You can also find me in Maje, Derek Lam, and Chloé, and if I can wear a piece of Samira 13 jewelry with an outfit, I always will.”

East End Shopping Haunts: “I mainly do my shopping in Sag Harbor and love balancing out my closet with a mix of designer and affordable pieces. Joey Wölffer is incredible for high-end shopping and it’s bohemian, which is perfect for my relaxed summer wardrobe. There’s a great boutique in Sag Harbor called Sunny; it always has amazing finds and unique clothes that I love as much as I love its name! Flashbacks is also the best place to buy trendy, inexpensive finds.”

Best Fashion Advice: “My stylist Fran Taylor told me, ’When you get dressed, give yourself a once over and take off that one extra piece.’ I’m also a firm believer that clothes don’t need to be designer or expensive to look amazing. I’m really a thrift shop girl; I also have my old faithful pieces that I’m attached to. I like vintage a lot; get me a vintage-shop-find Chanel jacket and a Gap T-shirt, and I’m ready to go!”

Never Be Caught Wearing: “That’s easy…neon!”

Summer Uniform: “A straw hat, sunglasses, and a maxi dress is my go-to outfit all summer long.”

Fashion Inspiration: “No question, my No. 1 fashion inspiration is Jackie O. I would say my style is Jackie O meets Zoë Kravitz—elegant, yet boho chic.”

2. Krista Schulz Corl, Philanthropist

Krista Schulz Corl

Personal Style Philosophy: “Maybe it’s because I’ve lived on the Upper East Side for two decades that I gravitate toward more classic, tailored, traditionally feminine silhouettes. I’ll incorporate trends when they complement my style, but I believe clothes should help you feel like the best version of yourself, so I wear what I think reflects my personality and lifestyle. I also believe fashion is truly art. I’ve spent years collecting Oscar de la Renta gowns because I adore their exquisite design and construction—they’re enduring pieces that can be worn for a lifetime. As Mr. de la Renta once said, ’Fashion is about dressing according to what’s fashionable. Style is more about being yourself.’ ”

Favorite Brands: “Oscar de la Renta for evening gowns; Carolina Herrera and Erdem for cocktail dresses; Balmain blazers and custom-tailored shirts for everyday life; Saloni and Borgo De Nor for summer dresses; J.Crew for classic wardrobe staples; Chanel for handbags; M.Gemi flats for walking the city; and vintage David Webb cocktail rings when I want to add a little sparkle.”

Summer Uniform: “As summer residents of Shelter Island, my family and I often get around via our boat, so I embrace nautical chic. My go-to look is Saint Laurent leather slides paired with high-waisted shorts and a striped La Ligne top. I top it off with a pair of Linda Farrow sunglasses and a Lola raffia straw hat. The Loewe Flamenco Knot Sailor Tote Bag is my favorite carryall for afternoons on the water.”

Never Be Caught Wearing: “All black in the summertime. Summer is the time to have fun with color, and we all need a little extra brightness in our lives now.”

3. Samantha Angelo, Creative Director of The Eye Travels


Samantha Angelo

Personal Style Philosophy: “It’s not what you wear, it’s how you wear it.”

Favorite Brands: “Alexander McQueen, Valentino, Fear of God, and my own lifestyle-inspired designs under the name Angelilli.”

Best Fashion Advice:  “Dress for yourself.”

Never Be Caught Wearing: “Leopard clothing and shoes made of cork.”

Must-Have Mask: “I design masks and recently opened an Etsy Boutique, The Eye Travels. I was searching for joyful summer masks in April and wasn’t able to find anything that I loved, not to mention the lead time was six-plus weeks. I decided to make my own masks. I made enough for my family and had some left over, so I told my Instagram followers to DM me if they were interested. I donated 100 percent profits to COVID-19 relief.”

Fashion Inspirations: “Diana Vreeland, Edward Enninful, and Pierpaolo Piccioli.”

4. Pamela Tick, DJ & Influencer

Pamela Tick

Personal Style Philosophy: “Less is more.”

Favorite Brands: “Ralph Lauren, Levi’s, Chrome Hearts, Nili Lotan, and Brunello Cucinelli.”

East End Shopping Haunts: “IMRIE in Westhampton; Homenature in Southampton; LoveShackFancy in Sag Harbor; RRL in East Hampton; and Love Adorned in Amagansett.”

Best Fashion Advice: “Go for the timeless pieces.”

Summer Uniform: “Mask, bikini, and ankle bracelets.”

Fashion Inspiration: “I’ve been noticing more and more how much young children influence my style. Something about their innocence and effortlessness.”

5. Julie Macklowe, Founder, The Macklowe American Single Malt

Julie Macklowe

Personal Style Philosophy: “If you’re going to be a bear, be a grizzly. Go for it, be unapologetic. Be bold, ballsy, and brilliant. My way is the Macklowe way.”

Favorite Brands: “Philipp Plein, Christian Cowan, Paco Rabanne, Marine Serre, Ali G/Fore Golf Wear, and Rapha cycling clothes.”

Best Fashion Advice: “Own your s**t. When you borrow, they own you.”

Summer Uniform: “Cycling bibs by morning, golf clothes by day, swimsuit in afternoon. The evening it depends if I have generally left my couch; right now, its mostly Paco Rabanne sweat suits. I dream for the day I need to wear a dress again.”

Fashion Inspiration: “My grandmother Dolly; she was extravagant and went to Atlantic City to gamble all night up until she died. She loved her jewels.”

6. Athena Calderone, Author, Interior Designer, Visual and Culinary Storyteller, Entertaining Expert

Athena Calderone

Personal Style Philosophy: “Elegant and sophisticated while remaining sexy AF.”

Favorite Brands: “Brock, Khaite, The Row, and Chanel. I mean, a gal can dream.”

East End shopping haunts: “Warm and Botanica Bazaar—both in Amagansett.”

Best Fashion Advice: “Simplicity is the keynote of all true elegance.” —Coco Chanel

Never Be Caught Wearing: “Not a fan of ruching or biker shorts. Also, overtly sexy is not my thing.”

Summer Uniform: “Always a white poplin dress.”

Fashion Inspirations:  “Jane Birkin and Audrey Hepburn.”

7. Sophie Bickley, Influencer

Sophie Bickley

Personal Style Philosophy: “Wear whatever makes you feel confident and fabulous. When you feel confident in your style that confidence exudes to others and in turn makes you look stylish to others, or so I like to think. Never be afraid to take risks with fashion. Don’t wear what everyone else is wearing or be basic; make yourself stand out by expressing yourself through your style.”

Favorite Brands: “Rixo, Ganni, Topshop, Zara, Moschino, Alice + Olivia, Cynthia Rowley, Zimmermann, Milly, Majorelle, Cotton Citizen, Staud, PatBO, and Ronny Kobo.”

Best Fashion Advice: “Don’t worry about always being on trend, and wear what makes you comfortable and feel good about yourself. Be you when it comes to your fashion sense, and don’t let other people influence it unless you love what they are wearing, too.”

Never Be Caught Wearing: “Khaki pants, wore those every day in boarding school. Done with that look and not just because I was forced.”

Fashion Inspiration: “My fashion inspiration comes from brands like Moschino, Rixo, Ganni, and Alice + Olivia. These are all super eccentric, mixing patterns, bright colors, and making every look super fun. One that you can’t miss and will turn heads and also look absolutely fabulous! Miley Cyrus is a good example of someone who make her outfits super fun but also stylish.”

9. Charlotte Bickley, Influencer

Charlotte Bickley

Personal Style Philosophy: “Wear what makes you feel like your best version of yourself.”

Favorite Brands: “Jacquemus, Area, Amina Muaddi, and Cult Gaia.”

East End Shopping Haunts: “Blue One, Tenet Southampton, Intermix, The West Side, and Cabana NYC.”

Summer Uniform: “An easy romper and bikini.”

Fashion Inspiration: “Elsa Hosk.”

10.  Sailor Brinkley Cook, IMG Model

Sailor Brinkley Cook

Personal Style Philosophy: “As long as I can jump, dance, and have fun in what I’m wearing…I’m happy.”

Favorite Brands: “Réalisation Par, Free People, and I love small vintage and thrift shops for those one-of-a-kind pieces.”

East End Shopping Haunts: “I don’t really do much shopping out here; I spend more time on the beach than in town. My favorite store is probably Deep Blue Vintage in Montauk; I always find the best gems in there.”

Summer Uniform: “A long boho skirt and a crop top over a bikini has been my go-to every day.”

Fashion Inspirations: “Sharon Tate—she’s forever a perfect example of effortless, feminine style—and Brigitte Bardot.”

11. Casey Fremont, Executive Producer and Art Production Fund

Casey Freemont

Personal Style Philosophy: “Wearing something uncomfortable is never a good look.”

Favorite Brands: “Rhode, Acne, Sacai, Ulla Johnson, Leon, Jimmy Choo, and Alice + Olivia.”

East End Shopping Haunts: “Goop Sag Harbor, MONC XIII, Ulla Johnson, and Jimmy Choo.”

Best Fashion Advice: “Wear a mask.”

Never Be Caught Wearing: “A MAGA hat.”

Summer Uniform: “Jean shorts and a button-down shirt over an Eres bathing suit, Chanel slides, and big black sunglasses.”

12. Kit Keenan, Designer

Kit Keenan

Personal Style Philosophy: “My style is very garden fairy/pink princess most of the time. Then there’s my 12-year-old-boy alter ego that comes out sometimes who just wants to wear boxer shorts and scour resale websites for vintage skate tees. I think it’s important to have balance and mix it up.”

Favorite Brands: “LoveShackFancy, Pyer Moss, and RE/DONE.”

East End Shopping Haunts: “Botanica Bazaar for all things wellness and skincare, and of course Cynthia Rowley.”

Best Fashion Advice: “Doesn’t matter what you wear, just as long as you are there.”

Never Be Caught Wearing: “A thong bikini.”

Fashion Inspirations: “Carolyn Bessette-Kennedy and Brigitte Bardot.”

13. Jenné Lombardo,  Entrepreneur

Jenné Lombardo

Personal Style Philosophy: “I always like things to be a little wrong, so my looks are never too precious. I grab a lot of influence from menswear, and always like to figure out how I can translate it to look sexy, feminine, and comfortable but dressy.”

Favorite Brands: “My go-to’s for evening are Ronny Kobo, The Attico, and Alessandra Rich paired with shoes from Brother Vellies. In the daytime, I’m low-key and love track suits that I pair with my Nikes or a clear-heeled shoe from Yeezy. Some of my favorite sweats are Pangaia and Amié Leon Dore.”

East End Shopping Haunts: “In no particular order (but these are all female-owned shops and the owners happen to be friends of mine): Love Adorned, Warm, Botanica Bazaar, Cynthia Rocket, and Wyld Blue. Also, Montauk Wine Company is an incredible black-female-owned business, which I always try to support.”

Never Be Caught Wearing: “I was about to say I would never be caught without a pedicure, but since COVID my feet have been pretty grim.”

Summer Uniform: “These days, because we have been in the midst of renovating our house, I am usually in head to toe Skims. They make great transitional looks that feel cute all times of day. Then when I have time to run to the beach, I usually wear Minimale Animale or Inamorata Swim because I like skimpier bottoms.”

Fashion Inspiration: “I like pulling inspiration from menswear and my kids. I have never really been one to—funny enough—obsess over fashion too much. I guess if I feel sexy and powerful, then it will be a good day.”

14. Johannes Huebl, Model and Photographer

Johannes Huebl

Personal Style Philosophy: “Style is not how you dress, but how you live. It’s part of a lifestyle, and it’s personal. You need to develop a signature and always be original and true to yourself. Avoid trends and fads. Be comfortable in your own skin and cognizant of your size and color.”

Favorite Brands: “Thom Sweeney, Brunello Cucinelli, and Frame.”

Best Fashion Advice:“To find a tailor.”

Never Be Caught Wearing: “Leather trousers, socks with sandals, and Speedos.”

Summer Uniform: “Soft cotton T-shirt from Closed, Uniqlo bermudas, and Castañer espadrilles.”

Fashion Inspiration: “When I travel I find most of my fashion inspiration in people I meet and pass by, such as visitors to Pitti Uomo in Florence and tailors in Savile Row.”

15. Don Lemon, Anchor CNN

Don Lemon

Personal Style Philosophy: “Fitted and tailored. Less is more. Clean, classic lines. Not a lot of frills on men.”

Favorite Brands: “Suitsupply, J.Crew, Levi’s, and Rhoback.”

East End Shopping Haunts: “Besides Emporium True Value Hardware store on Main Street in Sag Harbor? Sylvester & Co. in Sag Harbor and J.Crew in East Hampton.”

Best Fashion Advice: “Don’t worry about labels and trends. Buy what looks good and fits well. And every grown man should have at least two tuxedos—one black and one midnight blue. Rentals are for teenagers.”

Never Be Caught Wearing: “Sandals.”

Summer Uniform: “If I have to go out, white or sand-colored jeans or khaki pants with a white or light blue linen shirt. White sneakers or Saba shoes. But mostly a swimsuit, a T-shirt, and barefoot on a boat or at the beach.”

Fashion Inspiration: “Steve McQueen—casual, cool perfection. Google Steve McQueen actor fashion. You’re welcome.”

16. Tripoli Patterson Owner/Director, Tripoli Gallery of Contemporary Art

Tripoli Patterson

Personal Style Philosophy: “Comfortable and functional.”

Favorite Brands: “Oakley, Xcel Wetsuits, Fallen Broken Street, and Recess Clothing Company.”

Never Be Caught Wearing:“A uniform.”

Summer Uniform: “Leonard Frisbie sweat suit.”

17. Harvey Newton-Haydon, Model

Harvey Newton-Haydon (Getty Images)

Personal Style Philosophy: “If it’s comfortable and presentable, you’re golden. I like the mix of slouchy loungewear with a hint of luxe. Luxe-lounge?”

Favorite Brands: “Arjé, Carhartt, Yeezy, Hermès, and Tom Ford. That being said, I’m a huge fan of Y,IWO, Stampd, Nike, and a sleepwear brand I recently worked with called Lahgo. The list goes on!”

Best Fashion Advice: “Don’t be the sheep, be the shepherd.”

Never Be Caught Wearing: “A shirt on a beautiful sunny day or the same outfit twice!”

Summer Uniform: “By day, consists of swimming trunks, T-shirt, a beach hat, and Oakley sunglasses; by night, the comfiest cotton sweatshirt with some vintage military trousers and Birkenstocks.”

Fashion Inspiration: “My wife [Jenné Lombardo] and I play off each other quite a bit, kind of unconsciously, too. I think we see what the other is putting together and then go in that direction, which normally means we end up wearing the same thing. It’s a problem when you have his and her of everything. We like the same styles, and I also like for her to think I look good in what I’m wearing.”

Read The Daily Summer to see who else made the list! 

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