Q: I’m headed to Napa for a food festival and need to keep my luggage light (so I have plenty of room for edible souvenirs!). How can I maximize my travel wardrobe? —Rebecca Wasserman, via e-mail

A: Two words: convertible clothing. These pieces work double- or even triple-duty, wherever you roam.

This two-sided silk dress (pictured) can go glam for cocktail hour (just add heels and sparkling accessories). $349, Durga-Kali.

A leather jacket with zip-off sleeves becomes a vest—great for both warm afternoons and cool nights. $1,210, Sandro.

Swappable straps—in white, red, and orange—make your timepiece a fashion statement. $2,980, Baume & Mercier.

One gold-filled chain + multiple interchangeable charms = a necklace to match every outfit. Charms from $28, chain, $309, KZK Jewelry.

A neoprene tote that isn’t just ultralight: turn it inside out for a printed bag-of-the-moment. $175, Rafe.

Reversible skinny jeans offer the versatility of blue denim and the swagger of a camo pant. $139, Cult of Individuality.

And for the man in your life: board shorts worth flipping over. $98, Tommy Bahama.

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Mimi Lombardo is the fashion director at Travel + Leisure. Have a packing dilemma? Need some tips and remedies? Send your questions to Follow @tltripdoctor on Twitter.