Tips and tricks for surviving gala season

Gala season in the Cayman Islands runs from the beginning of October to about the end of June, so that means nine months of dinners, cocktails, gowns, jackets, dry cleaning and Advil. 

As someone who has hosted a great number of these events, I feel I’m in an excellent position to hand out some advice on how to navigate the gala dinner. It can seriously boil down to a game of survival. 

Booking tickets  

You can absolutely book tickets in groups of twos and threes, but then you may be seated at a table with people you a) don’t know; or b) don’t care for. The best way to avoid the Awkward Table Dynamic is to get together with friends ahead of time and book a table. Some galas sell out earlier than others. For example, the Breast Cancer Gala sells out months in advance, so you’ll want to book early for that one. Worst case scenario, if two of your friends can’t make it, hopefully you can sell those tickets to people you know. Crisis averted. 

Tip: Ask if there are discounts for table bookings. Often you’ll get a percentage off, versus booking individual or couples tickets. 

Getting there early  

I don’t know if you’ve noticed, but valet is not a given at these events, and when it is, it can be expensive. Hotel properties have limited spaces – for valet and self-park – and that means if you get there late, you could be mincing through the bushes and bog in your Louboutins. 

Honestly, so many people are over their legal drinking-and-driving limits by the time the night is over, they should be taking a round trip in a taxi regardless. However, if you insist on driving yourself, plan to get there within 15 minutes of the cocktail hour start time. It means you won’t have to wait for ages in the valet line and you won’t miss out on a parking spot if there is no valet. 

Tips: Leave the large SUV at home if you can – it’s tougher to find a space with one if you have to self-park. Call friends going to the same event and cab-share. 

Dress code  

Most of the main galas are black tie, which means a gown for the ladies and a tuxedo for the men. If you’re attending a good number of these events over the eight-month period, that can add up to mucho moolah. One of the major disadvantages of living on an island of this size is that 50 percent of the attendees tend to be the same for each gala, so for most, wearing the same outfit is not an option. 

When I was booked to host the Breast Cancer Gala in 2014, I scoured the local boutiques and Internet for pink dresses. My first question: when did sleeves go out of fashion? I swear, every site had either prom and quinceañera gowns or mother-of-the-bride outfits with scalloped accents and random lace everywhere. How about a “Still hopeful” category? 

I was about to give up, but then someone recommended Super Stitch to me. Y’know what? I got a gorgeous, pink taffeta skirt with a hoop undergarment for only $180. It was fitted to me and was exactly what I wanted. 

Tip: Look into a local seamstress before you spend loads of dollars overseas. It’s usually less expensive than buying retail and you know it will fit. If you insist on buying online from huge retailers like Alibaba that manufacture most items in China, make sure you get your dress size correct. My XL in the U.S. was XXXXL in China. Tres depressing. 


Maybe it’s just me, but I do not understand why women or men wear shoes that look good but feel like they’re walking on diamonds. Maybe the thinking is, “I won’t have to walk much;” “I’ll be sitting down all night;” “they look fantastic.” Lemme tell ya, there is nothing worse than being uncomfortable every time you stand or walk. Remember that there is a cocktail hour before the doors open, which will test your tootsies’ endurance even before you sit down. The toilets are also a walk from the ballroom and then you have to make it out to your car. 

If you insist on wearing Kardashian torture devices on your feet, make sure you bring along a pair of foldable slippers or you’re sporting a recent pedicure. 

Tip: Hand on my heart, I have worn long skirts, gowns and trousers so I can don a pair of sneakers underneath them. I may be no Audrey Hepburn, but I’m comfortable. I need to concentrate on hosting rather than feeling like Cinderella’s ugly sister in beautiful, sparkling, towering, bunion-inducing stilettos.
I dare you to try it, just once. 

Hair and makeup  

I learned the hard way that if you don’t book an appointment with your salon weeks or even months in advance, you could be left with no way of getting your hair or makeup professionally done. 

Frankly, I’ve never been high maintenance, but after seeing images of myself hosting an event with gray roots and black under my eyes, I yelled “Ermahgerd!” and vowed to never be caught in that position again. Even if you’ve missed out on a visit to your favorite salon or makeup artist, that doesn’t mean you have to show up looking like Magenta from Rocky Horror Picture Show. 

There are glorious “cheats” available on the market to help you cajole your coiffure into some semblance of a style. For example, Rock Gorgeous Hair, a premier salon on the island, carries a number of products to save you in an emergency. 

When you have silver soldiers marching across your scalp, a product like Oribe Airbrush Root Touch-Up Spray can really save the day. “If you don’t have the time to get your hair colored and you’ve got an event to attend, this spray is a lifesaver,” said Francis Omar, co-owner and hair stylist at Rock Gorgeous Hair. “It comes in a number of colors and completely covers up any gray roots to carry you over until you can visit the salon.” 

JoJo Cowin, owner and hair stylist at Utopia, tries to instill in her clients the importance of booking appointments well in advance, particularly around the holidays, but concedes that sometimes people get busy and then can’t get in anywhere. 

“My advice, under those circumstances, is to get yourself some Alterna Caviar Anti-Aging Dry Shampoo to remove excess oils and give your hair some lift,” she said. “Then use hot rollers or the Keratin Complex Transformer Interchangeable Styling Rod to create some bouncy curls. 

“Just pin your hair up or to the side and you’re good to go!” 

When it comes to makeup, make sure you choose products that can go the distance. It’s humid out there, so if you don’t want to look like a zombie, apply makeup that will stay in place. 

“I would recommend Kevin Aucoin Mascara,” said Sharron Eyers, owner of Le Visage and professional makeup artist. “It won’t budge, even if you wear it to the gym, but then comes right off with water. That’s the beauty of it.” 

Tip: I swear by the L’Oreal gel eyeliner (pot and brush) that I was given as a gift earlier this year. That stuff is like epoxy resin until I remove it with makeup remover at the end of the night. No more “Whatever happened to Baby Jane?” eyes! 


Remember that a lot of photos are taken at these events by friends and professional photographers. If you don’t like being caught unawares, keep your eyes peeled at all times for a lens and learn to pose with your best side forward. Most celebrities have been taught and trained to know at precisely what angle they look their finest.  

For example, look up pictures of Giuliana Rancic. She clearly knows her left side is her strongest one. 

As I’m on the microphone a lot, I don’t get the luxury of posing, hence all those shots of me apparently with a volleyball stuck in my neck. Don’t be a volleyball neck victim – know how to pose! 

Tip: Practice in the mirror at home or get a friend to take photos of you (selfies are not the same) at different angles. 


Apply makeup that will last through the night, or you’ll end up looking like a zombie.
Getty Images


Wearing comfortable shoes will have your toes thanking you at the end of the night.


This root touch-up spray will save your bacon if you can’t get a hair appointment before the gala.


Marc and Karina Langevin have certainly mastered the right poses for pictures. – Photo: Chris Court


They’re the devil in disguise.

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