, , , ,


Over Memorial Day, DiploDad, DB2 and I went to the Maldives. It’s a beach place – kind of like going to Florida, and we stayed at a resort. Since it’s the summer, and so many folks are headed to the beach, I thought I’d give my tips for Packing Like a Boss for a weekend beach trip.

This packing list assumes that you’re going to spend most of your time in the water or on the beach, chilling. It also assumes that you’re going to restaurants for your meals, or that someone else is at least doing the cooking. I’d probably make a few changes if I needed to cook dinner – but maybe not. It also assumes two overnights and flight time.

Ok – let’s get packing!

The list:

  • Four shirts. One of them should be a cotton shirt that could arguably be ironed. One of them should be a tank top. The others can be whatever you want, but should be comfortable and go either super casual or dressy casual, depending on how you accessorize.


  • OK, so really five shirts. Something fun that reminds you of home, where you came from, or something you love. With a logo.


  • A solid color scarf/dupatta in a color that goes with the two dressy casual shirts. I like to pack a colored one, but cream or black may be more your style. You could also go the crazy route and pack a beachy print that clashes with everything, which would be awesome.
  • One pair of solid color shorts that go with pretty much everything. I like white, but khaki, navy, or black can be good options. Just keep in mind two things: dark colors suck in heat, and white will call attention to that Wonder Woman underwear if you wear it underneath. Consider yourself warned.


  • One pair of linen pants. Again, go with a neutral. Same warnings for colors apply.
  • One casual skirt. I recommend a black stretch skirt. It packs well, you can usually rinse it in the sink if you have a stain emergency, and it goes with pretty much everything. If it suits whatever else you’ve packed and you have another color, go for that instead. If you’ve mostly solid tops packed, you could even pack a matching print. I like something a little less on the sporty side and more towards classic so that I have more evening options, but if you wanted to, you could totally pack one of those Columbia or LL Bean skort things.
  • One sundress or maxi dress. If you are going out at night, and you’re in Beach Land, you could arguably get away with tromping through dining establishments in a beach cover-up and your swimsuit or a crappy pair of cutoffs and a tie-dye t-shirt with a risqué logo, but don’t. Go the classy route. Not only will you feel fabulous, it will prevent any embarrassment if you should inadvertently run into an old boyfriend or your 3rd grade teacher. Stranger things have happened, trust me.


Given these basics, you’re looking at something like this for your land-based outfit options:


On to the beach!


  • I personally find it better to go the bikini route. Because you can do this:

Not only that, if you are diving, it’s easier to get in and out of things, and makes the pit stop after a long swim that much quicker. Invest in a good suit – buy separates, and while Target may have some cheapie options, if you’ve any kind of bust, you will want to visit Water, Water, Everwhere or another swimsuit specialty shop to get supportive tops. As an added bonus, it will hold up even longer, so go ahead and lay out the cash. I like to pack one in black and then a cute suit I have with two separate top options in a color I know I look fabulous in. Color definitely matters if you’re showing that much skin, so choose carefully.

For those of you who are not comfortable with the two-piece option, throw in at least two one-pieces. You’ve got room, trust me.

  • A swimshirt. Let’s get real, people, there’s this thing called skin cancer, and you want to avoid it. Again, invest in a quality top. Cheap ones not only won’t hold up that long, they also won’t provide adequate sun protection.


  • A good, packable hat. As long as we’re on the topic of sun protection, don’t forget the hat. Wide brim, collapsible. Make sure you’ve a wide enough brim to cover your neck. Target has a great selection of these every summer, and they ring up at about $15. If you’re not near a Target, check out some of the local tailors, especially in Africa – they tend to make things like hats out of scraps or ends of fabric. My friend, C, has one that I am dying to swipe. No matter what your fancy, you have a lot of options with hats – pick a neutral, pick one that matches most of your wardrobe, or go crazy and pick a bold, fun color you wouldn’t otherwise wear. Nothing says summer like a bright orange, pink, or yellow hat.


  • Beach cover-ups. I like a shirt-style cover-up that you can use as a casual dress over your suit when you head to breakfast on your way to the beach. I also like to bring a pareo – a giant scarf – for when I’m actually on the beach and just want to run somewhere else for a minute. Wrap it around your waist as a skirt, or put it around your back like a towel, cross one corner over your chest, bring it around your neck, and then repeat with the other side, securing it around your neck – bingo – halter dress. I tend to use the shirt-style cover-up only for the trek to and trek from the beach. Not while I’m parked in a beach chair.


Next Step: Accessories!

  • Let’s talk jewelry. Yes, you want some. No, you don’t want to bring Aunt Tilly’s special cocktail ring. Bring a couple of things you regularly wear, and don’t bring anything you would not be able to replace or would absolutely die if you lost. A few pairs of earrings in colors you’ve packed, a classic necklace, a fun bracelet or two, maybe a ring, and you’re done. Just keep in mind that whatever you’re wearing should be something you can wear with more than one outfit. Pack them in one of those jewelry cases I mentioned in this post – https://diplomom.com/2016/05/17/packing-like-a-boss-the-business-trip-edition/

Jewelry Collage

  • Two pairs of shoes. You’re going to a beach resort, so I’d propose two pairs of flip-flops – one “fancy” and one rubber pair for ratting around in. You don’t want to deal with heels unless there’s a boardwalk or an area where you’re able to walk around in those cute little sandals. If you do have that available, toss in those heels as an “extra” if you have room. You’ll be wearing the “fancy” flip-flops on the plane anyway.


  • Sunglasses. I travel with two pair because I tend to misplace things. I throw one in my bag and one in my purse.

And the basics:

  • A nightgown, five pairs of knickers, and a bra or two – if you need a strapless bra, toss it in, although you could probably get away with the double strap thing if you wanted to and didn’t care about your grandmother rolling over in her grave. Your call. Make sure that whichever bra you pack is a different color from the one you’re planning on wearing on the plane.
  • Go easy on the makeup – let your natural beauty shine through, and you’re going to have the holiday glow, so don’t cover it. Mascara and lip gloss are nice though. For other products, put in some travel sizes of your daily products. You can acquire quite a selection of these from hotel travel, the drug store, and samples from where you buy your regular cosmetics. Don’t forget to ask the salespeople when you buy that 15 oz. $40 moisturizer for a few sample sizes. And by a “few”, I mean about 10. While the goal is to make it through the airport without having to check a bag, you also want to avoid skin cancer, so go ahead and try to sneak in a full-size bottle of sunscreen. If it doesn’t make it through, you can buy it once you arrive. I have about a 75% success rate on sneaking it in – don’t tell TSA, OK?  Pack it in one of these:


Finally, what are you wearing on the plane?

  • Shoes. Comfy ones.
  • Neutral tank top. You might even wind up wearing it later on instead of other shirts, so keep that in mind when choosing.
  • Neutral sweater or jacket. It gets cold on the plane, so you’ll need it, even if it will be 40C when you arrive at your destination.
  • Neutral scarf. See tank top advice above when choosing the color.


Done! That’s it –


Pack it up, grab your tickets and let’s go – the beach awaits!


Styling courtesy of DB1.