Have you ever seen “that guy” at an all-inclusive resort who shows up to the nicest a la carte restaurant in a football-themed tank top and bare feet?

That is fashion mistake number one at an all-inclusive resort.

How about someone who completely overdoes it at a destination wedding in sequined, multi-layer formal wear and sky-high stilettos on the beach?

You guessed it—all-inclusive resort fashion mistake number two.

I’ve got five other fashion mistakes and tips and tricks that solve these problems. So you can pack for that all-inclusive vacation or destination wedding economically and thoughtfully.

Here’s why you need to read this:

1. The world’s best all-inclusive resorts generally have a “beachy casual” (read: semi-formal) dress code for fine restaurants.
2. The following tips and tricks will decrease your “what do I wear?” stress level and make packing easier, with suggestions for general resort wear and themed events like weddings.
3. Our “definitely not what to wear” tips could save your life (I’m joking, but trust me… stilettos on sand is a living fashion nightmare).

I’m not focusing on this today, but be aware that there can be dress codes for all-inclusive sporting amenities like an onsite tennis court or the Greg Norman-designed golf course at Sandals Emerald Bay. So, if you want to play, bring the proper attire.

Let’s have some fun with all-inclusive resort fashion!

Fashion Mistake: No Footwear or Inappropriate Footwear

Our barefoot footfall fan would be restricted to the beach at an all-inclusive resort in the Caribbean or Mexico, but the odds are stacked that any stiletto-heeled wedding guest will sink right down like it’s quicksand.

If you’re dining at an all-inclusive resort or attending a destination wedding, the best solution is a quality pair of low-heeled shoes or sandals with smart details. If you really want a heel, go for an open-toed wedge or block heel.

All-Inclusive Resort Fashion Tip: Flat sandals are great for female and male travelers and offer various styles. You can easily pack two pairs: one with sparkly accents for a destination wedding and one pair made of EVA with a 1.5-inch sole to give you height.

Fashion Mistake: Super Casual Is Never “In” at All-Inclusives

Yes, you’ll be spending a lot of time in swimwear at an all-inclusive, so you can relax about that when you picture the pool or the beach. But getting into a restaurant without a decent swimsuit cover-up may be hassling or embarrassing.

All-Inclusive Resort Fashion Tip: Search online for “best swimsuit cover-ups” to find a stunning variety of styles and colors that pack easily, stay dry, and slip on quickly. Many of these looks are so fashion-forward (dresses, jumpsuits, sarongs) you’ll wear them anytime.

Fashion Mistake: Upstaging a Beach Bride

You don’t want to outdo the bride at a destination wedding, the same way you never would at home!

Another thing to consider is the material you’re wearing. Let’s use our sequined, multi-layered wedding guest as an unfortunate example—wearing an intricate, heavier dress on the beach risks tracking up a lot of sand on a windier day. Hugely uncomfortable decision!

All-Inclusive Resort Fashion Tip: I love this article on beach wedding guest dresses by one of our staff writers. The links might not be active, but the fashion is still on point. Also, look for good materials for travel that roll up for easy packing and are wearable without wrinkling.

Fashion Mistake: Not Reading the All-Inclusive Fine Print

It’s not hard to know how to pack for an all-inclusive vacation, but you should always check for a dress code. Why risk losing out on an unforgettable vacation experience or being denied entrance based on your attire?

All-Inclusive Resort Fashion Tip: I took this research directly from the website of my favorite all-inclusive resort:

• “Resort Casual” is the standard dress code for all areas of the resort, including buffet restaurants and casual eateries by the pool and beach. Swimwear must be covered, and shorts, jeans, t-shirts, and polo shirts are suitable gender-neutral attire.
• “Resort Casual” swimwear cover-ups like lacy maxi dresses, shorter sarong dresses, rompers, and jumpsuits are on point. I’d wear a slip under a mesh swim cover-up just to be sure.
• Important point: “Resort casual” always means shirts and footwear when food is served, although Barefoot By The Sea is one notable exception, as the name suggests!
• “Resort Evening” wear takes it up just a notch—so don’t worry about having to pack too much or adhering to any strict fashion rules that will make you feel less comfortable on vacation.
• The “resort evening” dress code specifies “dress pants or jeans for men,” I suspect they’re talking about premium stretch denim for jeans because the material is comfortably lightweight for any season.
• I also researched the “resort evening” dress code for Hyatt’s vacation properties, and it states that women can choose “a nice pair of jeans, slacks, or a skirt.”
• “Resort evening” tops are indicated as long or short-sleeved dress shirts with or without collar. The Hyatt dress code defines a top as a dressy “blouse” for women.
• “Resort evening” dress codes are pretty serious about this—no shorts, t-shirts, sleeveless shirts, sneakers, flip flops, slippers, hats, or caps are allowed at finer sit-down restaurants at an all-inclusive resort.

Did I leave something out? If you’re wondering about the best dresses for “resort evening” wear, I left the best for last!

Fashion Mistake: Overdoing “Resort Evening” Wear

I’ve learned from this mistake, packing too many “resort evening” wear dresses because I was worried about looking too “beach bum” at a fancy all-inclusive resort. Cruisers might think this way, too, because evening wear on some cruise lines is decidedly more formal.

The real truth is you’ll fit right in at most all-inclusive resorts with lightweight, easy-to-pack maxi dresses, semi-formal cocktail dresses, halter dresses, or even a lacy jumpsuit.

All-Inclusive Resort Fashion Tips: I searched online for “resort evening wear dresses” and was pleasantly surprised when a list of “party/cocktail vacation” dresses from Macy’s appeared in the search results.

There were fantastic choices, including a stunning “crinkled minidress” in a “worldly blue” shade with flowing sleeves—this style flatters everyone.

My other favorite on the Macy’s site is a “flyaway leg crepe jumpsuit.” The crepe material is wrinkle-resistant and great for travel, and the short slit on the wide legs is just a yummy fashion statement!

I can also recommend these styles for travelers who are vacationing at an all-inclusive and also attending a destination wedding. My only concern is an outfit that’s white or creamy colored because you don’t want to clash with a beach bride—so go for a lighter pastel shade.