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What Should I Pack For A Warm-Weather Winter Vacation?

It’s chilly outside. Clouds scud, skies darken, the wind reddens our cheeks. A perfect time for warm-weather vacations. But how to pack well for heat when you’re cold. And, more practically, how to buy a bathing suit when you don’t even want to take off your sweater?

We’ll rely on “use cases,” same as for European vacations, and business wardrobes. (I’ve previously addressed the questions of vacations by a pool, here, and coverups, here.

Let’s think tropically today. Start with bathing suits. At a resort, the usual packing priorities are reversed. You wear bathing suits and occasionally put on something else.

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You will want:

  • 3 bathing suits (yes, 3 if possible, wet bathing suits are horrid). This year I’m looking at a) sophisticated colors b) ruching c) high-waisted bikinis. Yes, bikinis. I’m tired of covering myself with wet stretchy fabric and the world, I think, can handle the sight of my midlife stomach without self-destructing. That said, I’m going to ask the bikini bottom to help out just a bit with restraint. And the ruching is for when I tire of my belly myself, or fear sunburn. That which sees sun rarely, suffers mightily by the beach.
  • 2 coverups (they are small, foldable, and it’s fun to have variety).
  • Sandals in multiple colors.
  • Sunglasses. If you need reading glasses, prescription sunglasses are worth the investment.
  • A hat with a wide brim. I have discovered that cloth hats win the category, as you can rest your head back on your chair while reading.
  • Of course, you’re also going to need sunscreen, unless the destination is luxe. In that case they provide huge pump bottles of the stuff everywhere, like gas stations on the New Jersey turnpike.

But where and how to buy said bathing suits? Well, this year I’m going to try online. Sure, it might be hard to find sizes etc. But that’s true in person too. And online purchases magically transform those godawful store dressing rooms into your own friendly bedroom. I found when buying my wedding shoes that ordering 6-7 pairs to try out made the final decision quite simple.

On Land

You’re also going to need day wear for land. I don’t like to eat breakfast, or any meal for that matter, in my bathing suit. Unless I’m right by the pool or sea. So I always pack long shorts and a couple of tees/tanks.

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You also want to consider other planned activities. Hiking? Yoga class? Tennis? Workout room? Pack the minimal requirements to protect your feet, and cover the relevant body parts, because it’s highly probable that you’re still going to wind up mostly in your bathing suit, mostly by the water. By the way, Wigwam hiking socks are a foot comfort miracle.

At Night

And then night falls. On these kinds of vacations I appreciate my cultural tradition of dressing for dinner. You’re going to want to shower off all that sunscreen and salt anyway, why not get fancy?

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I know exactly what I’ll bring for a 5 night trip,

  • Loose pants. I have invested in a soft white pair from Black Crane, via Grechen’s Closet and Totokaelo. They are a little warm, but I think with a tank and gladiator sandals they’ll be great for evening.
  • 3 dresses – I like them loose, or light, or both. Specifically, I’ll bring my Dressed USA lavender shift and the 8-year old Tori Burch skirt, along with my Christopher Kane wedding rehearsal dress for one night in the fancy restaurant, dressed down with very bare sandals. Maybe some simple pearl studs.
  • Even when my feet are fine, I don’t wear heels to the beach, or anywhere near it. They undo all the serenity. I’ll substitute black jeweled flats, bronze flats, and Havaianas in multiple colors.
  • A white cotton/linen cardigan. I don’t find wraps helpful, in the tropics. Wool is to be avoided at all costs, and silk/cotton is often stiff.

And Don’t Forget

A few other categories worth considering:

  1. Flourishes – I accessorize with jewelry, rather than scarves and belts. Another cultural and family tradition, most likely. I tend to embellish for vacation, with bangles and dangles. However, Sturdy Gals always bring screwback stud earrings to swim in. No fools we. I also bring metallic hair elastics or hair forks for updos – hair tendrils are lovely and romantic but they have a way of finding their way into your mouth just as you’re trying to stuff it it with rock lobster.
  2. Makeup – All I wear at the beach is some concealer or tinted moisturizer with sunscreen, mascara, and a sheer lipstick or lipbalm. Anything else bugs me. Whether it’s the humidity or the desire to throw aside civilization, I’ll leave to you.
  3. Airplane gear – I’ve found it best to dress for the destination and then cover up with one big layer. Warm coat, hat, scarf, and gloves, over a tee or even tank top. I fly in loose jeans, which are OK under a long coat for passage through the cold zones. Put flip flops in your tote. Which reminds me, bring a tote or beach bag. Enjoy the outdoor baggage claim, and the tropical plantings that begin before you even leave the airport.

And there you go. Here’s to the warm winds of evening on your ankles and shoulders, and walking on paths so quiet you can hear the ocean just around the corner.

Shopping Inspiration for 2016 Holiday In The Sun



32 Responses

  1. Try Melissa Odabash bathing suits, also cover ups on Net-A-Porter. Love them, great fit and very comfortable.

    Going to Antigua in March – need some jeweled flat sandals for sure. Thanks for the link!

    1. Word for the day Cir-cu-i-tous. Now I will use it in a sentence: on a recent circuitous FB romp, I saw your comment @ Reggie, then I clicked your name [you are just so snazzy] and, ohmigosh 2 new babies!…wait, continuing on w/ our word for the day, one of your photos lead to what I’d consider THE missing garment in the bride’s honeymoon suitcase, namely the caftan/coverup you’re wearing 8-12-12 under the LB arch. Where did you find that? Seems like you wore a similar one in another print, as well. That’s what I’d live in on this kind of resort holiday, round the clock essential. I love it, it looks sensational on you!

    2. Thanks Flo – those are from Roberta Roller Rabbit, where I do get a lot of cover ups and lounge-y stuff. And yes, also baby clothes too :)

  2. I love that Ann Mashburn popover! All of her clothes are eminently comfortable and practical–and perfect for a vacation!

  3. Can you believe I’ve never done a tropical holiday? Closest we came was a mostly poolside week in northern Portugal one warm late-June. . . Fun to imagine packing for a vacation like that, especially since my swimming is almost completely confined to our own beach and I stretch out my swimsuit’s life for (quite) a few years. . . And it’s probably too late to change now, no?

  4. My family (husband, 2 teen daughters, 2 teen friends) will be in the Bahamas next week for Thanksgiving, which will be a far cry different from the chilliness in Virginia right now.

    I’m backing three Lands End bathing suits — bought online, tried on in the privacy of my home, and worth every penny. Dresses, shoes, etc. for dinners out. Some yoga clothes, which will, truth be told, also be worn sometimes at non-yoga times. A cashmere cardigan or two for layers. And beyond that, I’m not going to worry too much about my wardrobe and just focus on having a relaxing and fun time.

  5. Nice looking choices.
    I like the mix of swim suits. If you go snorkeling or jet skiing the 2 piece suits look like they’ll stay put better.

  6. This is wonderful! Thanks for planning my February getaway for me! Now, (if I may be so bold!)would you do the same thing for my European cruise (10 nights) coming up in August?! I’m already feeling intimidated–go figure~

    Always a pleasure, Lisa. You always hit it out of the park!

    1. my @L.A., My pleasure! I have never done a cruise in Europe, but if I can get my Mom to give me some hints, I will pass them on:).

  7. The idea of long shorts makes me blanche! Also, I would pack daytime sundresses to wear instead. I love all your other suggestions! Have a wonderful time.

  8. Don’t swim in jewelry. Whether salt water or pool, if you’re wearing precious metals it’s really bad for them.

  9. Wonderful choices full of happy anticipation! I’ve started to travel with only screw-back earrings; anything else is too easy to lose, with all the activities, hats, waves and every kind of fun.

  10. Thank you most kindly, Sensei. An excellent tutorial, and I am a-flutter over the magenta jeweled sandals. I had a lovely and most Sturdy time in FL, walking miles a day, barefoot on the beach. Heaven. But I clearly need to up my evening game.

    i plan a return to Hawaii this winter, with a certain trepidation: Mr. Artsy and i discovered a wonderful place on our honeymoon, and came back every year. Alas, it was the only resort on the Big Island to be rendered completely unusable by the Japanese tsunami several years ago. It was unique in many ways, very low-key and private, with a pretty casual dress code. We will be forced–forced, I tell you! ;)–to try another resort, which will be fresh and fun, but I’ll need to be channeling some inner Grande Dame when choosing my clothes.

    I wonder: are your packing choices informed at all by fear that the airline will lose your luggage? i pack with this in mind, which means I leave my Artsy fun stuff at home and no doubt dress too casually.

  11. Looks like you have your clothes well in hand…don’t forget a pashmina for the air conditioning on the plane or in a waiting area. The shock of coming back to a cool climate can give you the chills. Enjoy your honeymoon!
    BTW I love Lands End for swim wear.

  12. These are such good problems to have! I really love that pink snakeskin print bathing suit. Your outfits sound perfect and thanks for the tip on those hiking socks–I’m going to get some asap, I’ve taken up hiking and need these!

    xo Mary Jo

  13. I could agree with most of the choices save for the waterfall cardigan. I have never cared for them, since it is the rare woman who needs or wants anything drooping or sagging on her body. But, outside of that, you have made me eager for a winter vacation :)

  14. I’m also a huge fan of the Camilla silk caftans. I’m hoping to find myself in Orlando this coming May and will be packing one. As well as my trusty Victoria’s Secret 2 piece bathers that have survived many a summer holiday at home and abroad.

    SSG xxx

  15. Just returned from 10 days in Mexico ,, Pacific side .. 90F, rain just stopped, hills all green.
    My favorite evening outfit is gauze flow-y pants (look like a skirt almost) and gauze loose top, or sometimes little T shirt top. Leather sandals for evening, regular flip-flops (Hav. or other that can get wet and sandy) for day. (never heels) Pareo/sarong definitely. If I am wearing earrings, that means I am dressed up!
    White wrinkle-y linen pants, Cut-Loose or other, can just rinse and shake-shake and hang to dry up on roof of my tiny hotel.
    I love this kind of dressing, but then I love tropical casual places.

  16. Ooh, warm weather holidays… It’s not far enough into autumn/winter for me to be pea-green with envy, but I’m tinted a delicate eau-de-nil at least.

    I think the closest we’re going to come this year is late summer in New Zealand aka a visit home which doesn’t require lots of swimsuits.

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