From Deck to Dinner; How to style your 7-day cruise

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New here? Make sure to check out The Caribbean Cruise Capsule Wardrobe first to discover the exact items we are styling in this guide.

The Realistic Day-to-Night Itinerary Matrix

Here is exactly how your wardrobe pieces work together in real life, ensuring you never wear a stained outfit or run out of clothes.

• Day 1: Embarkation & Sail-Away

  • Day: Linen Trousers (8) + Oversized Shirt A (11) (tucked or half-tucked) + Cardigan or Shawl (15) over the shoulders for flight and boarding comfort. (Optional: Bring a bathing suit in your carry-on if you would like to take a swim before your suitcase arrives at your stateroom).

  • Night: Sundress A (1) + jewelry for your first dinner at sea.

• Day 2: Sea Day & Elegant Night #1 (The Captain's Welcome)

  • Day: Luxury Swimsuit A (6) + Multi-Way Kaftan (16 or 17) for a relaxed day by the pool.

  • Night (Formal/Elegant Night #1): The Showstopping Cocktail Dress (4) + statement jewelry. This is your moment to make a beautiful entrance for the biggest elegant night of the cruise. Bring your Pashmina or Cardigan (15) for over your shoulders when dining in cold air conditioning.

• Day 3: First Port of Call (Historic Island Tour)

  • Day: Sundress B (2) paired with comfortable leather slides and a sun hat for exploring historic streets.

  • Night: Satin Maxi Skirt (10) + Silk Camisole Top (14) or Fine Resort Knit Top (13) + (optional) Oversized Shirt B (12) tied at the waist with sleeves rolled up.

• Day 4: Beach Excursion & Casual Dining

  • Day: Tailored Shorts (9) + Oversized Button-Down Shirt B (12) worn open over your fresh Luxury Swimsuit B (7).

  • Night: Sundress C (3).

• Day 5: Sea Day & Relaxed Elegance

  • Day: Luxury Swimsuit B (7) and for by the pool with Kaftan (16 or 17) styled as a dress for brunch on deck.

  • Night: Linen Trousers (8) + Oversized Button-Down Shirt A (11), fully buttoned, collar popped, statement earrings.

• Day 6: Second Port of Call & Elegant Night #2

  • Day: Tailored Shorts (9) + Fine Resort Knit Top (13) for a morning of boutique shopping at the port.

  • Night (Elegant Night #2): Minimalist Silk Slip Dress / Cocktail Dress B (5). Polished, high-end, and memorable. Pair it again with your pashmina or shawl (15) when feeling chilly while in the dining room, taking a stroll on deck or watching movies under the stars.

• Day 7: Last Day in Paradise

  • Day: Sundress A (1) (repurposed for a relaxed daytime walk along the beach).

  • Night: Satin Maxi Skirt (10) + Fine Resort Knit Top (13) + Cardigan (15) for farewell drinks.

• Day 8: Disembarkation Day

  • Day: Sundress C (3) or your Linen Trousers (8) + Oversized Shirt A (11) + Cardigan or Shawl (15) over the shoulders for comfort during your flight home.

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