The Vacation Shirt Hack: How to Get 3 Looks from 1 Hawaiian Shirt

Pack one Hawaiian shirt. Get three completely different looks out of it over a long weekend — no repeat-outfit guilt, no overstuffed suitcase. The trick celebrity stylists use is treating a printed shirt like a layer, not a statement piece. Wear it open over a tank for day one, button it up with clean shorts for day two, tuck it in with a belt for a nicer dinner on day three. Same shirt, different energy every time. It's the highest-ROI item you can pack for a warm-weather trip.

Here's how to pull it off, with styling cues from someone who dresses people for a living.

Why the Hawaiian Shirt Is Your Best Vacation Packing Move

Most guys overpack for vacation because they think of each outfit as a complete, separate unit. Shirt one goes with shorts one. Shirt two goes with shorts two. By day four, the suitcase looks like a laundry explosion.

A Hawaiian shirt breaks that pattern because it's inherently versatile:

• The print provides visual interest, so your bottoms can stay simple
• The relaxed structure works open as a layer OR buttoned as a standalone top
• The collar gives it enough formality for a nice restaurant
• The pattern disguises minor wrinkles (critical for suitcase living)

Think of it as a wearable Swiss Army knife. One piece, multiple functions.

What a Celebrity Stylist Says About This Approach

Britt Theodora — the celebrity stylist behind Pete Davidson's Met Gala look and styling work with Kevin Bacon and Elliot Page — laid out this exact philosophy when styling COOFANDY's Hawaiian shirt for Maxim (in a sponsored feature).

Her take: "What I really love about this, if you pack this for a weekend I would do a tank top under it and open it. If you have necklaces you like to wear, that's a fun time to show that off."

It's part of what she calls "Energy Styling" — building outfits around effortless cool and intentional refinement, rather than rigid rules. The idea is that confidence comes from looking like you made a choice, not like you followed a formula.

That's the mindset behind all three looks below.

Look 1: Open Layer + Tank Top (Daytime Exploring)

The vibe: Relaxed, beach-town cool. You're walking a boardwalk, grabbing coffee, browsing shops.

How to build it:

• Hawaiian shirt unbuttoned, worn open
• Solid-color tank top underneath (white, black, or grey)
• Swim trunks or casual shorts
• Slides or canvas slip-ons
• Sunglasses + a simple chain or pendant if you wear jewelry

Why it works: The open shirt becomes an outer layer — it catches a breeze, creates movement, and frames the outfit without adding heat. The tank keeps you cool underneath while the collar on the Hawaiian shirt saves the whole look from "just rolled out of bed" territory.

Britt's tip applied: This is the necklace moment she mentioned. An open neckline with a pendant or chain adds a subtle detail that makes the look feel intentional.

Best for: Pool days, beach walks, casual lunches, farmers markets, resort lobby hangs.

Look 2: Buttoned Casual (Afternoon Activity)

The vibe: Put-together without trying too hard. You're doing a boat tour, meeting friends for drinks, or exploring a new town.

How to build it:

• Hawaiian shirt buttoned up (leave the top button undone)
• Chino shorts or tailored swim trunks
• Clean white sneakers or leather sandals
• Watch or bracelet

Why it works: Buttoning the shirt transforms it from a layer into a proper top. The print does all the visual work, so you need zero accessories to look interesting. Paired with clean shorts and shoes, it reads as "I know what I'm doing" without any stiffness.

Styling note: Roll the sleeves once or twice if the shirt has longer short sleeves. It tightens the silhouette and looks more deliberate.

Best for: Day drinking, boat days, casual group activities, afternoon sightseeing, Instagram photos where you want to look like you belong on vacation.

Look 3: Tucked Smart (Evening Dinner)

The vibe: Elevated resort. You made a reservation somewhere that isn't a taco stand — maybe a rooftop bar or a seafood spot on the water.

How to build it:

• Hawaiian shirt fully buttoned, front-tucked or full-tucked into pants/shorts
• Linen trousers or longer chino shorts (7-9" inseam)
• Leather belt (matches your shoes)
• Loafers or clean leather sandals
• Minimal watch

Why it works: Tucking a camp-collar shirt instantly elevates it. The structure of the tuck, combined with a belt and closed-toe shoes (or elevated sandals), shifts the entire outfit from "vacation casual" to "vacation smart." You're wearing the same shirt as this morning — but the context reads completely differently.

Styling note: A front tuck (just the front center portion tucked in, sides loose) keeps it relaxed. A full tuck with a belt is more polished. Match to the restaurant's vibe.

Best for: Resort dinners, rooftop bars, date night, sunset cocktails, any situation where flip-flops and a tank would feel underdressed.

How to Choose the Right Hawaiian Shirt for This Hack

Not every Hawaiian shirt works equally well across all three looks. Here's what to prioritize:

Print scale: Medium-scale prints (not too tiny, not giant flowers) are the most versatile. They read well buttoned up AND as a layer.

Color palette: Pick a shirt with 2-3 colors max that work with neutrals. A navy-and-cream palm print pairs with white, black, tan, and grey bottoms. A shirt with 6 competing neon colors limits your pairing options.

Fabric: Rayon or viscose drapes beautifully and resists wrinkles. Cotton-linen blends breathe well but wrinkle more (fine for casual looks, less ideal for the tucked dinner version).

Fit: Slightly relaxed through the body — not skin-tight, not boxy. It needs to look good both open (where extra fabric creates movement) and tucked (where excess fabric bunches awkwardly).

Collar: Camp collar (open, notched lapel) is the most versatile. It works buttoned without the top button looking stiff, and looks intentional when worn open.

Browse COOFANDY shirts: COOFANDY Hawaiian Shirt

Vacation Packing List: Building Around the Hawaiian Shirt

If you're doing a 4-5 day warm-weather trip, here's how one Hawaiian shirt anchors your entire packing list:

Tops (4-5 pieces):

• 1 Hawaiian shirt (your triple-duty piece)
• 2 solid tank tops or tees (for layering and off-days)
• 1 linen button-down (backup dinner option)
• 1 polo or casual henley

Bottoms (3-4 pieces):

• 1 pair swim trunks (solid color)
• 1 pair chino shorts
• 1 pair linen pants or longer shorts (dinner)
• Optional: 1 pair athletic shorts (gym/run)

Shoes (2-3 pairs):

• Slides or sport sandals (daytime)
• Clean sneakers (everyday)
• Loafers or leather sandals (dinners)

That's a carry-on-sized wardrobe for nearly a week — and the Hawaiian shirt is doing triple duty across three of those days.

FAQ

Won't people notice I'm wearing the same shirt three days in a row?

Unlikely, especially if you're rotating between different groups or activities. The three styling approaches create enough visual difference that the shirt reads differently each time. But if it bothers you, space the wearings across days 1, 3, and 5 of your trip.

What color tank top works best under a Hawaiian shirt?

White is the safest — it works with every print color. Black adds contrast and feels slightly edgier. Grey is the neutral middle ground. Match to one of the lighter colors in the shirt's print for a more pulled-together look.

Can I wear a Hawaiian shirt to a nice restaurant?

Absolutely — tucked in with chinos or linen pants, a Hawaiian shirt is perfectly appropriate for 95% of resort and vacation restaurants. The camp collar gives it a sophistication that a regular printed tee can't match. Only skip it for truly formal spots (jacket required).

What's the best fabric for a vacation Hawaiian shirt?

Rayon or viscose for minimal wrinkles and good drape. Linen-cotton blend if you prioritize breathability and don't mind some creasing. Polyester blends for maximum wrinkle resistance but slightly less breathability.

Does this hack work for cruise ship dressing too?

Perfectly. Cruises have the same day-to-night progression: pool deck → port excursion → ship dinner. The three Hawaiian shirt looks map directly to those transitions.

Sources

• Maxim, "COOFANDY Teams with NASCAR's Christopher Bell & Celebrity Stylist Britt Theodora to Rev Up Your Style," 2026 — maxim.com