Dress Code: How To Pack For Your Vacation


In this installment of Dress Code, we’ll take on packing. Even if you’re not going away this weekend, chances are at some point in the coming months, you will — herewith, a few tips to avoid bag-bloat and no-skivvies crises.

I know this hyper-organized woman who not only has a travel bag perma-packed with first aid stuff and mini toiletries, but also takes a Polaroid of every garment she packs so that if an airline loses her luggage, she can get accurate reimbursement. I’m not like this. I’m a naturally bad packer. I tend to panic and think I’ll “need” three vintage formals and five cookbooks for a 3-day trip to visit friends in the Boston suburbs, and then only get there to discover that, in fact, what I “need” — and failed to pack — was underpants. It also took me a really long time to get over my addiction to absurdly heavy, picturesque thrift-shop luggage. So! I’ve devised a few formulas that help me. I use a checklist that includes, yes, underwear, plus toiletries, passports and clothes. I try to pick stuff that goes together, pieces that multitask. And I check the weather report.

Obviously, there’s no one formula for every trip or every person. If you’re going on, say, a hiking trip, bring hiking boots. Tick country? Light clothes are a good idea. And the chance of a formal occasion means something dressier. I’ve tried to give suggestions for 3 general, 3-day trips. Use it as a starting point and adjust accordingly! Remembering, as always, that rules are made to be broken.

But always good ideas, even for a short trip:

  • Bring multitasking clothes — by this I mean stuff that, with the right pairing and accessories, can be used for various occasions.
  • Check the weather. You may get a vague idea at best, but in the warmer months it’s the difference between packing closed-toe shoes and being stuck with sandals in a thunderstorm.
  • Bring underwear. Duh.
  • Bring easily-rolled, squished and packed things whenever possible.
  • In a pinch, a necklace or earrings can dress up a look; you can afford to bring a small stash of options, since this stuff takes up so little space.

Also, there’s a very smart “roll it all up” strategy to fitting everything you could possibly need in your carry-on (ten days’ worth!), courtesy of a flight attendant. Check it out here.

Now let’s talk specific types of vacations! We’ll stick with three general types of summer getaways; feel free to toss out ideas for other types of trips in the comments, and may the wisdom of the masses help you even more.

The Beach Weekend
A beach trip, be it near or far, has the advantage of light, rollable clothes. Better still, they can be super-cheap! The following is a basic suggested packing list – I’m assuming that, unlike me, you’ll take undies, PJs etc. as a given.

  • 2 tanks or tees
  • A light top, also good as a cover-up
  • 1 swimsuit, 2 if you’ll be swimming a ton
  • 1 sundress, also good as a cover-up
  • 2 bottoms: Shorts, a light skirt, or summer pants
  • Flip-flops
  • Slightly dressier sandals
  • Light jacket or sweater
  • Some kind of large beach bag
  • A hat and sunglasses are always a good idea

A City Weekend
This jaunt is all about walking, so you’ll want comfortable shoes. There’s also a chance you will be eating somewhere respectable or going to a show, so it’s a good idea to have one getup than can be dressed up. I’m a big fan of a versatile dress that packs small and can be dressed up with other (still comfy!) shoes and maybe some jewelry. And bring a light jacket or wrap: museums and theatres get chilly!

A rough suggested-packing list:

  • 3 respectable tees or other tops
  • 1 pair of either jeans, pants, or nicer shorts — or a versatile skirt (2 if you aren’t into dresses!)
  • 1 versatile dress
  • Casual jacket or sweater
  • 1 pair tested (read: not new) walking shoes
  • 1 pair more polished, but still comfortable, shoes
  • Purse of your choosing (and a crushable tote or shopping bag is always a good idea for impromptu puchases)
  • Clutch if you really need to gussy up
  • Light scarf that can do double-duty as a wrap

Country Weekend:
Again, if you’re going to be doing something specific — hiking, sports, camping — obviously pack for that. Here, I’m thinking of a visit to somewhere more rustic and less beachy, but obviously I’m going to generalize:

  • 1 pair jeans or long pants suitable for potentially tick-dwelling, poison ivy/oak-infested and thorny terrain. If you’re sure you’ll encounter one of these, maybe bring 2.
  • 1 pair shorts – or not, if you hate shorts. Make it more pants.
  • 4 tops: tanks, tees, maybe a button-down.
  • 1 sweater or sweatshirt
  • 1 light jacket, or a fleece if you’re somewhere that gets chilly in the evenings
  • 1 pair athletic shoes for walking. Whether it’s hiking boots, sneakers or even wellies depends on weather and terrain.
  • 1 alternate pair of casual shoes — nice for a trip into town or when your others are drying/mud-caked.
  • Bathing suit if you’re near a lake
  • A bandana is always useful, be it for hair-wrangling, neck-cooling, or jauntiness.

Also, there’s a very smart “roll it all up” strategy to fitting everything you could possibly need in your carry-on (ten days’ worth!), courtesy of a flight attendant. Check it out.

For all of our handy Dress Code guides, go here.

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