Isle style: What and when to wear where

It’s fair to say most of us got comfortable wearing our “yard clothes” — clothes we wear at home — while working from home.

As more people returned to the workplace, some businesses have introduced more relaxed dress codes and policies because, let’s face it, we can do most jobs regardless of what we wear.

In the Cayman Islands, the average corporate environment often allows for relaxed office styles, going with a business casual approach Monday through Thursday, followed by the beloved casual Friday.

Business casual is one of those attire categories where the words seemingly contradict each other, but it’s a mix-and-match affair where jackets meet slacks and heels meet jeans.

Some offices still lean more to the dressing “corporate” side — so no to the jeans — while others allow you to dress more casually, like wearing shorts on a Friday.

However, there are some settings where you are likely expected to dress professionally.

woman in dress walking
Dart's Vice President of Hospitality Laura Skec wears business casual attire in Camana Bay.

There’s often an expectation for you to “dress your best” and make a lasting first impression when in an interview. This usually means dressing in traditional business attire.

If your interview is online, then you can get away with wearing pyjama bottoms because nobody’s going to know. However, for an in-person interview, the expectation is professional wear, from head to toe. This is not a one-size-fits-all approach for all organisations, but better safe than sorry.

There are no grey areas when it comes to dressing for court. Visitors to the courthouse, especially lawyers, are expected to enter wearing jackets, or at a minimum, ensuring shoulders are covered with all clothing at appropriate lengths.

You may be prohibited from entering the premises if you arrive wearing items such as shorts or slippers, so avoid those if you don’t want to be late for a court date.

The Cayman Islands is still mostly traditional when it comes to dressing for places of worship. Aim for what’s commonly known as your “Sunday best," which often resembles professional wear as it typically involves dressing modestly.

Though some places of worship welcome you to “come as you are,” the more traditional ones do uphold a certain standard of dressing and some may have specific requirements as part of the religion’s practice.

Though you are not expected to arrive at various commercial establishments dressed professionally as a customer, it’s worth noting some settings such as banks, supermarkets and most retail stores enforce a “no shoes, no shirt, no service” policy. So be sure to keep a shirt and pair of shoes handy, and if you're applying for a loan at a bank, dress professionally.

This article originally appeared in the November 2021 print edition of Camana Bay Times.

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About the author

Ariel Thompson is a content manager at Dart, having joined the company in 2017. A lifelong writer, Ariel was born and raised in the Cayman Islands before studying abroad at Oakwood University in Huntsville, Alabama, for her degree in public relations and film and television. With eight years of experience in communications, Ariel joined Dart after working as Cayman International School’s first marketing communications officer. As her name would suggest, Ariel is a Disney fan and has a singing voice to rival The Little Mermaid’s. She loves to conceptualise TV and movie scripts and hopes one day to be a director. When in Camana Bay, Ariel can be found enjoying Mizu Asian Bistro + Bar’s Pad Thai, or shopping with friends and a scoop of gelato in hand.

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