Clothing Ideas for a Fall or Winter Trip to the Tropics

Published in: Just For Fun

Clothing ideas for a fall or winter trip to the tropics
Hawaii, Christmas 2009

Lucky MBB reader Rachael is taking a potentially BIG tropical trip this January, and she’s shopping for packing ideas.


“My boyfriend and I are taking a trip to Hawaii the first week of January, and I’m at a loss for what to bring. I am possibly the palest person and still have scars from a bad sunburn in the Bahamas when I was a teenager, and I do not want that to happen again.

I also think that on this trip my boyfriend will propose because he’s terrible at keeping secrets and has slipped more than once. I need to know what will take me from hiking to the beach and an engagement but keep it all easy to travel.”

— Rachael

Hey Rachael,

Congrats on your upcoming trip (and hopefully proposal)! ๐Ÿ™‚ Sounds like the makings of a marvelous month.

Whenever I travel to someplace tropical, I try to pack as many multitasking products and pieces of clothing as possible. Clothing-wise, for a one-week trip, that means a few lightweight, versatile dresses in stretchy fabrics that resist wrinkling, because I can easily dress them up or down.

When I head to the beach, I’ll slip a dress over my bikini, step into a pair of flip-flops, put on a wide-brimmed hat (great for extra sun protection to complement SPF), and drop a sarong or a wide, lightweight cotton scarf into my beach bag, just in case I end up in direct sunlight for a while and want some extra coverage for my shoulders.

I like Coolibar’s Silk Infinity Scarf ($39). Made from hand-dyed twisted silk, it’s lightweight, hardly takes up any space in a bag or luggage, and provides excellent UV protection. One caveat, though: it’s dry clean only.

How about a hat? Clockwise from the black hat on the lower left: Coolibar Shapeable Poolside Sun Hat ($45); Collection XIIX Bold Stripe Floppy Paper Straw Hat ($25); Kinda Shady Straw Sun Hat ($14); August Hat Bead Trim Paper Straw Kettle Hat ($19)

For nice dinners or nights out on the town, I’ll jazz up a dress with a bold necklace, bracelet or earrings and put on a pair of strappy sandals (dressier than flip-flops). I’ll also add a button-down sweater and/or another scarf if it gets chilly at night.

Which reminds me — I love bringing scarves when I travel, even to the tropics. They’re easy, affordable ways to switch up an outfit, and if they’re wide enough, you can even wear them as a wrap on a cool night.

As for hiking, dresses can still work, believe it or not. I’ve done it before. Granted, not on hard-core hikes, but for easy trails.

If you don’t mind looking a little silly in a dress and hiking boots, a dress should do you just fine. For more strenuous activities, though, don’t forget to pack a pair of shorts and a t-shirt in your beach bag or backpack (TIP: If you’re trying to make every cubic inch of packing space count, keep in mind that you can usually find super cheap t-shirts for sale at many tropical tourist destinations, including Hawaii).

With autumn here, this might be a good time to grab some great outgoing summer stuff on sale. Here’s a few ideas I found online…

Nordstrom dresses on sale from the left: BP. Double Scoop Tank Dress ($12); Stem Pleat Front Dress ($20) and Remain Knit Dress ($25) dresses from the left: Alternative Apparel Racer Tank Grey Dress ($40) and Sidewalk Bistro Striped Dress ($38)

O’Neill dresses from the left: Ever ($44); Heat ($44); Tough Love ($40); and Long Distance ($40)

Clothing ideas for a one-week trip to the tropics in fall/winter
  • A few lightweight dresses
  • Shorts and tees (although keep in mind that you should be able to get some cheap tees at your destination)
  • Jeans
  • A wide-brimmed hat
  • Scarves
  • Bold jewelry (necklaces, earrings and/or bracelets)
  • Flip-flops and sandals
  • One or two button-down sweaters
  • Your swimsuit (of course)
  • Board shorts and a rash guard (if you plan to do any surfing)

You might also want to look into a few lines that are known for their outdoor gear, like Coolibar, which I mentioned a earlier; The North Face; Land’s End and Sungrubbies, to name just a few.

I hope this helps! Have a blast on your trip, Rachael. I have a feeling you’ll love Hawaii. And don’t forget to let me know about the proposal, because I love a good proposal story. ๐Ÿ™‚

Your friendly neighborhood beauty addict,


P.S. For more packing tips and a few skincare and makeup packing ideas, check out How Do You Pack Your Makeup When You Travel?, Be a Good Student of Travel Makeup with a Clear Pencil Case, When It Comes to Travel Makeup…, Which Skin Care Products Go with You When You Travel?, 5 More Packing Tips for the Perennially Over-Packed.


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So far, 10 people have commented on this article. How cool is that?

  1. Lindsey says:

    Is that the porch of the Surf Rider? I love that hotel!

    I second dresses. I usually pack a handful of dresses, 2 cardigans in different colors that coordinate with each, a couple pairs of shoes (1 flat, 1 heeled pair), and a huge lightweight scarf that doubles as a shawl. Or you can do a couple of skirts and a pair of shorts with several different tops to mix and match with all of them instead of dresses if you don’t already have a bunch. That way you can dress each bottom up or down. If it’s a well-traveled trail to the beach, a lot of the dresses Karen recommended will look really cute with a pair of bright canvas sneakers ๐Ÿ™‚ Have fun!

  2. Sonya says:

    I love floppy hats and desperately wish I could wear them! (Unfortunately, they look silly on me.) I never heard of O’Neill but from the looks of it, the dresses are gorgeous! Definitely something I need to check out.

    Great tips, as always! ๐Ÿ™‚
    Sonya recently posted … Givenchy Gloss Interdit Ultra-Shiny Color Plumping Effect in 07 Glamorous Fuchsia – Review, Photos, Swatches

  3. sarahc says:

    Good ideas! I have to remember scarves and something costumey jewelry. The scarves are brilliant, and good call on a rash guard. ๐Ÿ™‚

  4. Zaynab says:

    Heyy girlies, just gotta say quickly absolutely love LOVE this blog!! And in reply to Rachael’s post, another thing which I find I have to downsize on is my make up!! I went away with my girlfriends recently to Spain and my saviours were

    MAC strobe cream

    Estee Lauder day wear plus tinted moisturiser – this is great when you go darker from tanning (self confessed sun worshipper!!) because the tinted moisturiser blends in with your skintone at any shade and it has a spf 15

    Bobbi Brown shimmer brick in bronze

    Urban Decay Ammo Box – an eyeshadow palatte with amazing colours from golds and nudes to turqouises and purples

    YSL mascara faux cilis waterproof

    MAC lipsticks in see sheer, girl about town, modesty and a handful of MAC lispglosses mainly bronze and nudes!

    So i had a maximum of 10 items of make up with me compared to my friend who had 3 make up bags with her weighing 7 kgs alone in weight and had to pay an extra baggage charge at the airport because her stuff was overweight!! I also didnt take any concealers with me (a brave step!!) because when i tan it doesnt suit me and also i think the sun evens out my skin tone so its one less item to carry! Hope this has been helpful in some way! ๐Ÿ˜€

  5. JoJo says:

    I so love this post…I am a floppy hat person and I’m drooling right now at the prices ๐Ÿ™‚

  6. Nina says:

    Karen, thank you! im not Rachael, nor am i going to travel, but i can still wear these dresses because we dont get winter til next year!

  7. nai says:

    great tips, karen! as a honolulu resident, may i add that if stores where you live don’t carry slippers (errr….mainlanders call em flip flops, i guess), shorts, swimsuits/bikinis, and/or board shorts (perhaps because they’re out of season), don’t fret. they’re very easy enough to find when you get here. all of the resort areas will have shops that sell them. if you plan on doing something with a lot of walking, then a pair of sneakers would come in handy.

    the lightweight dress tip is spot on!

    rachael, in case you wondered, your sweetie can get away with tshirts, a pair of jeans, one pair of dress shoes, slippers (errr…flip flops), a pair of sneakers, a couple pairs of shorts, one or two collared shirts. i’d say one pair of regular shorts and maybe two pairs of board shorts would be good enough. guys wear board shorts to practically everything except dressy events. a long sleeved shirt and dress pants are necessary only if you’re going to a restaurant that requires them.

    oh! if you are going to the Big Island (Hawaii Island) and you plan on visiting Volcanoes Natl Park, know that covered shoes are required.

  8. Oh yeah~~ these are the types of clothing we wear in sunny Singapore all year round! =D

  9. Michelle says:

    These are all such cute ideas!

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