Vacations are the perfect time to showcase effortless yet elevated style. Whether you’re heading to a tropical island, a European getaway, or a chic city escape, curating the right outfits ensures you feel confident, comfortable, and camera-ready. Celebrity stylist Elizabeth Stewart—known for dressing Hollywood’s A-list—brings you 10 perfectly styled vacation outfits that blend fashion and function.
1. The Luxe Resort Set: Breezy and Chic
Best for: Tropical resorts, beach destinations
- What to wear: A linen two-piece set (crop top + high-waisted wide-leg pants) in neutral tones like beige or white.
- Styling tip: Pair with strappy sandals, a woven tote, and oversized sunglasses for an effortless yet polished look.
- Bonus: Choose linen or cotton fabrics to stay cool and wrinkle-free.
2. The Effortless Maxi Dress: Glam with Ease
Best for: Dinner by the sea, sunset cruises
- What to wear: A flowy maxi dress with a bold print or pastel hue. Go for lightweight fabrics like chiffon or silk.
- Styling tip: Elevate the look with statement earrings, gold sandals, and a sleek low bun for a sophisticated touch.
3. The European Stroll Look: Tailored Meets Casual
Best for: Exploring European streets, sightseeing days
- What to wear: A tailored blazer over a ribbed tank paired with high-waisted shorts and classic sneakers.
- Styling tip: A crossbody bag and oversized sunglasses add Parisian flair while staying functional.
4. The Swimsuit-Layered Outfit: Poolside to Brunch Ready
Best for: Beach clubs, lounging by the pool
- What to wear: A chic one-piece swimsuit doubled as a bodysuit, layered with a sheer sarong or linen wrap skirt.
- Styling tip: Add strappy sandals, a wide-brim hat, and delicate gold jewelry for an Instagram-worthy look.
5. The Travel Day Look: Cozy and Polished
Best for: Long flights, road trips
- What to wear: A matching knit set (sweater + wide-leg pants) in a soft, neutral color.
- Styling tip: Slip-on loafers or stylish sneakers, a cashmere wrap, and a structured carry-on tote make for a chic and practical airport look.
6. The Dinner Date Elegance: Sultry Yet Classy
Best for: Fancy dinner nights, cocktail parties
- What to wear: A silky slip dress in jewel tones like emerald or deep burgundy.
- Styling tip: Elevate with strappy heels, a mini clutch, and a sleek updo for red carpet-worthy elegance.
7. The Adventure-Ready Ensemble: Sporty Chic
Best for: Hiking, exploring nature
- What to wear: High-waisted biker shorts, a cropped tank, and an oversized linen button-down for a relaxed yet active look.
- Styling tip: Complete with chunky sneakers, a bucket hat, and sleek sunglasses for a fashion-forward sporty vibe.
8. The Classic Nautical Look: Seaside Sophistication
Best for: Boat trips, seaside lunches
- What to wear: A striped Breton top tucked into high-waisted white linen pants.
- Styling tip: Pair with espadrilles, a straw hat, and cat-eye sunglasses for timeless summer style.
9. The Effortlessly Cool Jumpsuit: One-and-Done Chic
Best for: Exploring markets, casual brunches
- What to wear: A utility-style jumpsuit in a neutral tone (beige, olive, or navy).
- Styling tip: Cinch the waist with a belt bag, add minimalist sneakers, and layer with gold jewelry for a put-together look.
10. The Night-Out Power Look: Bold and Statement-Making
Best for: Rooftop bars, vibrant city nightlife
- What to wear: A structured corset top paired with high-waisted trousers or a satin mini skirt.
- Styling tip: Add lace-up heels, bold red lips, and a slicked-back bun for undeniable confidence.
Vacation Fashion: Do’s & Don’ts
Do’s:
- Pack versatile pieces that can be mixed and matched for multiple outfits.
- Prioritize comfort without compromising on style by choosing breathable fabrics like linen, cotton, or silk.
- Stick to a cohesive color palette to make outfit coordination easier.
- Invest in quality footwear that is both stylish and practical for walking.
- Layer smartly with lightweight jackets, blazers, or wraps for effortless transitions from day to night.
- Accessorize with statement sunglasses, a chic hat, and minimal jewelry to elevate simple outfits.
- Choose fabrics that are wrinkle-resistant or easy to steam to keep your outfits looking fresh.
Don’ts:
Choose uncomfortable fabrics that don’t breathe well in warm weather.
Overpack by bringing unnecessary outfit options that you won’t wear.
Rely solely on trends; instead, opt for timeless, well-fitted pieces that suit your personal style.
Wear brand-new shoes for long sightseeing days without breaking them in first.
Forget about climate-appropriate clothing—check the forecast before packing.
Ignore functionality when choosing handbags; opt for a crossbody bag or tote for practicality.
Pack only casual wear; bring at least one elevated outfit for unexpected upscale events.
Final Thoughts: Packing Like a Stylist
- Choose versatile pieces: Stick to a neutral color palette with a few statement pieces for easy mixing and matching.
- Pack stylish but functional shoes: Limit to three pairs—comfortable sneakers, chic sandals, and elegant heels.
- Layer smartly: Lightweight layers like a linen blazer or silk scarf transition from day to night effortlessly.
With these 10 curated vacation outfits, you’ll feel effortlessly stylish no matter the destination. Elizabeth Stewart’s signature styling advice ensures that each look is both practical and polished, making your vacation wardrobe stress-free and stunning.
FAQs
How should I dress stylishly for travel?
The key to looking stylish while traveling is balancing comfort with polish. Opt for well-tailored, breathable fabrics like linen, cotton, or soft knits. A monochromatic or neutral-toned travel outfit, such as a knit set or a blazer with tailored joggers, gives an effortlessly chic appearance. Stick to sleek sneakers, loafers, or ankle boots for footwear, and accessorize with a structured tote or crossbody bag for practicality.
How many outfits do I need for a 7-day vacation?
A 7-day vacation typically requires a capsule wardrobe approach to avoid overpacking. Aim for 8 to 10 versatile pieces, including:
Three to four tops that can mix and match with different bottoms
Two to three bottoms (shorts, skirts, or trousers)
One or two dresses or jumpsuits
Two pairs of shoes (comfortable sneakers/sandals and one dressy option)
A light jacket or blazer for layering
Accessories like scarves, jewelry, and sunglasses to change up looks
Choose multi-purpose items, such as a swimsuit that doubles as a bodysuit or a maxi dress that can be dressed up or down.
How can I look put together on holiday?
Looking polished on vacation is all about intentional styling and minimal effort. Stick to outfits with clean lines, well-fitted silhouettes, and a cohesive color palette. Keep accessories simple but effective, like a statement handbag or structured sunglasses. A neat hairstyle, subtle makeup, and well-maintained nails also enhance your overall look. Lastly, wrinkle-resistant fabrics and travel-sized steamers help keep your clothes fresh throughout the trip.
