Sundresses with statement jewelry are perfect for an evening on the town in Key West — Photo courtesy of Karrie Porter Photography

Although Kenny Chesney sings “No Shoes, No Shirt, No Problems,” that advice won't get you far in Key West.

The "Southernmost City" – which is closer to Cuba than Miami – has a laid-back Caribbean vibe, but some fashion rules still apply.

How does one navigate the waters of Keys casual to Keys formal? (Yes, there is such a thing.) Use these tips to pack for your perfect Florida Keys vacation.

A cute coverup can take you from a day at the beach to shopping in the boutiques — Photo courtesy of Amra Beganovic / clubfashionista

On the Water

Whether you’re spending the day lounging under a tiki hut or plying the crystal waters in a kayak, polarized sunglasses are a must.

Women should load their waterproof beach bags with a bathing suit, flip-flops and a shady hat. Throw in a coverup; a lightweight tunic dress or colorful sarong should do the trick. Meanwhile, guys should bring board shorts or swim trunks, a brimmed hat and T-shirt.

Keys beaches can be rocky, so water shoes are a wise investment. Don’t forget the high SPF sunscreen. Lobster-red skin makes the worst accessory.

Done for the day? It’s time to don those coverups and tees, especially if you plan on visiting the quirky boutiques and cafes in Old Town. Shoes and a shirt are required at most restaurants.

Remember: Key West is still a small town, and residents prefer you didn’t peruse the grocery store in your bikini.

Dress for the heat when sightseeing in the "Southernmost City" — Photo courtesy of Amra Beganovic / clubfashionista

Sightseeing

For a day exploring the island's attractions, you’ll want to dress for the heat. Daytime temps in the Florida Keys usually hover between 80 and 90 degrees, and humidity can make it seem higher. Bring clothing made with natural fabrics like 100% cotton, silk or linen.

Shorts with cute tank tops or sundresses are great choices for the ladies. Wear comfy shoes such as flat sandals or sneakers. You’ll be doing a lot of walking or biking, and Duval Street – the main drag – is a mile long. Blisters would definitely take the pep out of your step. Go light on the makeup, and downsize your huge boho purse.

Men can wear shorts and T-shirts, but no tank tops. (Sleeveless shirts are okay, if you must.) Even though stores on Duval Street sell shirts with vulgar sayings, wait until you get home to wear one. If you wouldn’t wear it at home, perhaps you should re-think that purchase?

Men can wear a collared shirt and khaki shorts to most Key West restaurants — Photo courtesy of Karrie Porter Photography

Night on the Town

Most of the restaurants and bars are open-air and casual, but don’t roll up in your beach wear.

For men, go with jeans or khaki shorts and a collared shirt – from polo to Hawaiian to fishing – and open-toe shoes like leather sandals.

Women, a sundress and strappy sandals fit in anywhere, but capris with a chic tank top, tunic or sleeveless blouse work as well.

Upscale eateries like Hot Tin Roof and Latitudes on Sunset Key request diners don resort or country club wear, so ask if they have a dress code when making reservations. Don’t worry: this still doesn’t mean jacket and tie.

Men can choose long khaki or linen pants and closed-toe footwear such as deck shoes or loafers (sans socks). If you didn’t pack anything that fits the bill, pop into World Wide Sportsman in Islamorada on your way south, and peruse their sizable men’s department. 

Ladies can put on heels, but it’s not necessary, especially if you plan on strolling Duval Street afterwards. Jazz up your outfit with statement jewelry or a colorful scarf, and bring a wrap or light sweater for breezy nights by the water.

Sunset Beach Wedding

The dress code for any wedding depends on the happy couple, so check your invitation for guidelines. If the bride goes for a barefoot-in-the-sand theme, both men and women can don resort wear.

The bride sticking with a formal gown? She may want her guests to dress accordingly.

Men can follow Cuban tradition and sport a linen guayabera, normally worn at festive occasions, untucked and in pastel colors. Can’t score one of those tropical staples? A silk Hawaiian-style shirt in muted florals will work. If jackets or vests are required, look for seersucker or linen, using a soft-hued palette. Pair with long cotton or linen pants and closed-toe footwear.

Women can wear bright, breezy dresses in natural fabrics matched with classy leather sandals or wedges and sparkly jewelry. Just remember heels and sand don’t mix. If you’re completely stumped, drop into Lilly Pulitzer for one of their famous shifts. Complete the look with a colorful wide-brim woven hat and Jackie O sunglasses.