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“My husband and I are heading to the Caribbean! Woohoo! I feel like a teenager about to take her first flight. But everything I ever knew about planning a vacation wardrobe — and packing light — has been wiped from my brain. Where do I start? What do I absolutely need? What will fit in my carry-on? I still want to feel like ‘me,’ just a bit more carefree.” — Ella, enchanted by the thought of leaving Toronto for a hot minute

Oh, let me travel vicariously through you, Ella! This query offered the chance to catch up with the most stylish packer I know, Toronto uber-stylist Susie Sheffman, who has shot dreamy editorial spreads and advertising campaigns all over the white sand beaches of the world. If anyone’s brain has retained the crucial life skill of creating a vacation capsule wardrobe and power-packing it into a carry-on, it is Sheffman.

“I always thought those pack-light people were such snobs,” says Sheffman. “But I do it anyway. On vacation, you want to leave your worries and your baggage behind, lighten your load.” Plus, she says, nothing zaps a vacation vibe faster than waiting hours at an empty carousel for a checked bag on the way home.

To live the carry-on life you have to take the time to plan ahead, which can be a fun thing to do as you envision all the fun times ahead you’re dressing for. “Make sure you think of at least two to three ways to wear everything you are bringing,” she advises.

A vacation wardrobe is something you should invest in over time. Build it the way you decorate your home, she says, mixing investment pieces with high street and vintage, “so it doesn’t look like you got everything in one Zara haul.”

Sheffman decrees you should take three good swimsuits and insists you try them on ahead of time, even if they aren’t new — not just to make sure they still fit, but to check the elastic isn’t shot. “Bring a small container of handwashing detergent,” she says, as chlorine and salt damage bathing suits. “Maintenance pays off in extending garment life.”

In the daytime you are likely to be wearing a bathing suit and coverup combo, and a great caftan is a lifetime investment, Sheffman says. “It exudes that kind of bohemian feeling you want to have, that feeling of freedom and fantasy.” A caftan will elevate your lunch-on-the-beach looks, and goes seamlessly from pool to cocktails. “I’m a big believer in belts,” she says. “They are an underrated accessory. It can dress up a flowy day piece for dinner.”

As for the clothing basics, Sheffman would never travel without an oversized white button-up shirt that can be worn loose, tucked or knotted at the waist. Also: “Bring two to three plain white T-shirts. For bottoms, she’s a big fan of white jeans. (Related advice: “Get Shout pens for stains. You can’t get them in Canada, but they are the best, so grab them wherever you see them on the road.”)

By her outfit math, you need two to four evening looks for seven nights away. Silky little tops work and fold down into nothing. “Bodysuits are in style right now, so make a good maillot bathing suit do double duty, paired with high-waisted pants or a long, loose skirt.”

Sometimes, one-piece dressing can be easier than separates, and a new summery dress will make a tropical night special. Sheffman recently styled a capsule collection for fashion retailer Andrews, and spied some cute and twirly floral dresses you can find there. “You want loose and flowy — that feels sexier in the heat,” she says. Look for “mood-enhancing” bright hues and bold prints: colour looks great amid the bright sunlight and bold blues of the Caribbean.

A linen shirt-dress is another good option. “Linen is timeless and better for travel than you think: all that tropical humidity is nature’s iron; the big creases fall out naturally.”

One thing you can’t forget, she says, is a cardigan. “You can throw it over anything and it always gets colder at night than you expect it to.” A soft shawl works, too, and is a plane essential — it could be fine wool or jersey, even an old-school pashmina. Go for a light colour, “maybe a soft pastel pink or lavender, to make it feel of this season.”

Sheffman has more travel packing tips: Put a little purse or clutch in the tote you are going to use all week and carry that on the plane. “Wear your bulkiest shoes on the plane, too, no matter how dorky you feel.” That would be trainers or hiking shoes; otherwise, Sheffman is “an admitted sandal addict” who reserves precious carry-on space for a pair of flat sandals, and poolside flip-flops or beach-hardy plastic Birkenstocks.

Sheffman’s mind is boggled by people who don’t decant their toiletries into travel-sized bottles; she keeps a loaded set of refillables at the ready. She also uses silky little packing bags to keep things organized (hers are from Eagle Creek).

Her last, and most resonant, piece of advice is to shop while you are away. “Always look to add something special to your vacation collection. It could be a scarf, some hoop earrings, an armful of bangles.” That way, you can bring your vacation home with you and build a wardrobe of accessories that narrate the story of your travels.

Pack a mix of investment pieces that will last a lifetime of vacations, practical basics and a few pops of fresh colour.

Andrews dress, $349, andrewsco.com SHOP HERE

Linen is a vacation classic; let tropical humidity do the ironing for you and settle into an artfully rumpled chill vibe.

Birkenstock sandals, $65, urbanoutfitters.com SHOP HERE

Plastic Birks tuck easily into a carry-on and go seamlessly from sand to sidewalk for a durable daytime look that’s a step up from flip-flops.

Everlane swimsuit, $105, everlane.com SHOP HERE

Bodysuits are back, and a one-piece bathing suit can do double duty to give you more mileage from your vacation packing list.

Madewell jeans, $163, nordstrom.ca SHOP HERE

White jeans are timeless and add a crisp finish to a vacation silhouette.

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