For Women

Daywear (Tropical Elegance Meets Wartime Practicality):

• High-waisted linen trousers or culottes

• Lightweight short-sleeve blouses with shoulder pads

• Cotton shirt dresses in tropical prints or solid brights

• Espadrilles or low-heeled sandals

• Wide-brim straw hat or floral headscarf

• Bamboo bangles and rattan handbag

• Red lipstick and winged eyeliner

• Hair styled in victory rolls or pinned curls

Eveningwear (Casino & Cabaret Glam):

• Off-the-shoulder or halter-style dresses in silk or satin

• Fitted bodice with full skirt or curve-hugging column gown

• Peep-toe heels or strappy dance shoes

• Bolero jacket or lace shawl

• Dangling rhinestone earrings or tropical flower hair clip

• Clutch bag and a dab of gardenia perfume

Beach & Leisure:

• High-waisted bikini or ruched one-piece swimsuit

• Sarong wrap or terry robe

• Cat-eye sunglasses

• Fan (both fashion and function)

• Embroidered slippers for lounging

For Men

Daywear (Classic Cuban Cool):

• Lightweight guayabera shirt (embroidered or pleated)

• Pleated high-waisted trousers

• Two-tone loafers or leather sandals

• Panama hat or fedora

• Pocket square and Ray-Ban-style sunglasses

• Optional: rolled cigars in a shirt pocket for the full effect

Eveningwear (Havana High Life):

• White dinner jacket or dark tailored suit

• Crisp dress shirt with a bow tie or open collar

• Spectator shoes or patent leather oxfords

• Gold watch or signet ring

• Hair slicked back with pomade

Beach & Lounge Looks:

• Knit polo shirt or casual cabana set

• Swim trunks with a vintage cut

• Terry cloth shirt or robe

• Leather slides or espadrilles

Accessories & Essentials

• Monogrammed lighter and vintage cigarette case

• Cuban cigars (real or prop, up to you)

• Travel-size domino set or deck of cards

• Linen fan or parasol

• Portable record player and Afro-Cuban jazz vinyl

• Guidebook or map of Old Havana

• Journal for stories you won’t tell later

• Embroidered handkerchief

• Classic cocktails: daiquiri, mojito or El Presidente (in a flask or just your imagination)