Dressing for the Occasion

As the owner of a number of professional service firms, I understand the importance of dressing appropriately for different situations. Resort evening wear is a specific dress code that requires a certain level of elegance and sophistication, while still maintaining a sense of relaxation and comfort. Although many are retired and avoid suits, jacks, or dress slacks, I will share my insights on how to dress for resort evening occasions, including elegant casual and formal resort attire.

When it comes to resort evening wear, the key is to strike a balance between being well-dressed and not overly formal. Men should opt for dressier shorts, pants, or nice jeans paired with a polo or other collared shirt. T-shirts, sleeveless shirts, and shorts are generally not acceptable for evening events. I recommend choosing neutral colors like khaki, navy, or white for a classic and timeless look. Footwear should be elegant sandals or close-toed shoes, such as loafers or boat shoes. Flip flops are too casual for resort evening wear and should be avoided.

Women have a bit more flexibility when it comes to resort evening wear. A casual dress is always a great option, as it can be dressed up or down depending on the occasion. Alternatively, women can pair a blouse with a nice pair of jeans, slacks, or a skirt. I suggest choosing fabrics that are lightweight and breathable, such as cotton or linen, to stay comfortable in warm weather. When it comes to footwear, elegant sandals or close-toed shoes are appropriate, but flip flops should be left for the beach or pool.

Elegant casual, also known as "casual elegance," is a step above resort evening wear and is similar to what you would wear to a country club or upscale restaurant. For men, this means a long-sleeve dress shirt with slacks and dress shoes. Shorts, t-shirts, and sandals are not acceptable for this dress code. I recommend choosing a dress shirt in a classic color like white or blue, and pairing it with well-fitted slacks in a neutral color like khaki or grey. Dress shoes should be polished and in good condition.

Women have a bit more leeway when it comes to elegant casual attire. Skirts or pants with a nice top or a dress are all appropriate options. I suggest choosing a dress or skirt that falls at or below the knee, and pairing it with a blouse or sweater in a complementary color. Avoid anything too revealing or casual, such as shorts or tank tops. Dressier shoes, such as heels or elegant flats, are recommended over sandals.

Formal resort attire is the most dressy of the resort evening wear options, and is often chosen for weddings and other special events. While the dress code is more lax than traditional formal wear, it still requires a certain level of sophistication. Men should wear a suit or a nice button-up shirt with a dinner jacket and slacks. I recommend choosing a suit in a classic color like navy or gray, and pairing it with a dress shirt and tie, or a pocket handkerchief. Dress shoes are a must, and should be polished and in good condition.

For women, formal resort attire includes full-length dresses and gowns, as well as nice pantsuits or skirts with a stylish blouse. I suggest choosing a dress or gown in a rich, elegant color like deep red or emerald green, and pairing it with simple, understated jewelry. If you opt for a pantsuit or skirt and blouse, choose a well-fitted, tailored option in a neutral color like black or navy. All outfits should be paired with a nice pair of heels or elegant flats.

Finding the right balance between elegance and comfort and meeting situational expectations can be difficult. Whether you're dressing for a casual evening event, an elegant dinner, or a formal occasion, the key is to choose well-fitted, appropriate attire in classic colors and styles. By following these guidelines and adding your own personal touch, you'll be sure to look and feel your best at any resort evening occasion.

Lastly, ignore those who make snide comments about being a classic Western cultural traditionalist.