Ever stood in front of your closet, suitcase open, torn between a breezy linen dress and cute espadrilles — wondering which outfit will survive beach winds, vineyard evenings, and a casual lobster roll lunch? If you’ve ever asked yourself what to wear in marthas vineyard, you’re not alone. The island calls for a mix of coastal-chic style and practical, weather-ready layers. Below I’ll walk you through outfit combinations, beauty tips, and packing-smart routines so you can look great and feel comfortable from Oak Bluffs to Menemsha.
Why Martha’s Vineyard Calls for a Different Dress Code
Martha’s Vineyard is equal parts nautical town, beach refuge, and upscale summer getaway. That means you’ll want pieces that are polished but relaxed, breathable yet camera-ready. Think texture (linen, cotton, seersucker), classic prints (stripes, micro florals), and accessories that handle wind and salt air.
Layering Essentials: The Island Capsule Wardrobe
Daytime Staples
- Lightweight linen or cotton sundress — easy, packable, and flattering.
- Striped tee or Breton top — a Vineyard classic that pairs with shorts or culottes.
- Cropped denim or high-waisted shorts in neutral tones.
- Breathable sneakers or leather sandals for walking cobblestone streets and wharves.
Evening and Transition Pieces
- Light jacket: a denim jacket, a linen blazer, or a thin utility jacket for breezy nights.
- Silk scarf or bandana to keep hair in place during windy dinners on the porch.
- Versatile midi dress that can be dressed up with wedges or styled down with flats.
Footwear: Comfort Meets Island Charm
Shoes should be both practical and pretty. Pack a pair of cushioned sneakers for bike rides and long walks, espadrilles or wedge sandals for casual nights out, and waterproof slides for beach days. Avoid overly delicate heels — you’ll be navigating wooden boardwalks and sandy paths.
Accessories That Elevate Every Outfit
- Wide-brim or straw hat to protect your face and add instant style.
- Classic sunglasses (polarized are best for glare off the water).
- Lightweight crossbody bag or woven tote — hands-free and camera-ready.
- Minimal jewelry: hoops, a pendant, and a few stackable rings keep it sophisticated but easy.
Beauty & Skincare Routine for Island Days
The sun, wind, and salt air mean your skin and hair need a little extra love. Start with a daily SPF — I recommend a broad-spectrum sunscreen (SPF 30 or higher) and reapply often if you’re outdoors. Hydration is key: lightweight hydrating serums and aloe-based after-sun gels calm sun-exposed skin. For more detailed recommendations, check out my skincare tips page.
Morning Routine
- Cleanse gently to remove overnight oils.
- Apply antioxidant serum (vitamin C) to protect against free radicals.
- Moisturizer + sunscreen. Use a tinted moisturizer with SPF for an effortless glow.
Nighttime Recovery
- Double-cleanse if you wore makeup.
- Hydrating night cream or a light retinol alternative to boost skin turnover.
- Lip balm with SPF isn’t necessary at night, but keep a hydrating treatment handy.
Makeup: Fresh, Resilient, Photogenic
Keep makeup beach-friendly and long-wearing. Think tinted SPF, cream blush, waterproof mascara, and a coordinating lip stain. If you want to glam up for a seaside dinner, add a cream highlighter and a neutral eyeshadow—smudge-proof formulas are your friend. Browse my makeup trends for current product picks and techniques.
Quick Island Makeup Look
- Tinted sunscreen or BB cream.
- Cream blush on apples of cheeks for a sun-kissed look.
- Waterproof mascara and brow gel.
- Tinted lip balm or stain that won’t budge after a lobster roll.
Outfit Combinations: Day-to-Night Looks
Below are five go-to combos that cover beaches, bike rides, harbor dinners, and casual evenings.
- Beach to Boardwalk: High-waisted shorts + striped tee + straw tote + slides + wide-brim hat.
- Vineyard Lunch: Linen midi dress + espadrille wedges + woven clutch + layered necklaces.
- Sunset Cruise: Lightweight trousers + silk cami + linen blazer + statement earrings.
- Casual Explorer: Linen jumpsuit + sneakers + crossbody bag + sunglasses.
- Dinner in Town: Wrap dress + block heel sandals + delicate bracelet + red lip stain.
Packing Checklist: Smart, Minimal, Photo-Ready
- 3 tops, 2 bottoms, 2 dresses, 1 light jacket
- 2 pairs of shoes (sneakers + sandals) + one optional dress shoe
- Hat, sunglasses, lightweight scarf
- Travel-size sunscreen, hydrating serum, waterproof mascara, lip tint
What to Wear in Marthas Vineyard: Tips for Specific Activities
Beach Days
Swimsuit under a breezy cover-up, waterproof sandals, wide-brim hat, and SPF. Pack a quick-dry towel and a mesh bag for wet suits.
Biking or Exploring
Comfortable shorts or bike-friendly romper, sneakers, a lightweight backpack, and sun-protective layers.
Formal Events / Vineyard Weddings
Opt for a flowy midi or tea-length dress in breathable fabric. Bring a shawl or light blazer for cooler evenings and choose block heels or wedges for lawn stability.
Frequently Asked Questions
1. What should I wear to Martha’s Vineyard in the summer?
Summer calls for breathable fabrics like linen and cotton, layered pieces for cooler mornings and evenings, comfortable shoes for walking, and sun protection — a hat and SPF are musts.
2. Are dresses a good choice for the island?
Yes—dresses are ideal. Choose midi or maxi lengths for versatility and wind-friendly silhouettes. Add a jacket or scarf for evenings.
3. How do I keep my makeup from melting in the heat?
Use lightweight, long-wear formulas: tinted SPF, cream-based products, waterproof mascara, and a setting powder or spray. Carry blotting papers and a lip tint for quick touch-ups.
Conclusion: Embrace the Island Style
Whether you’re planning a weekend escape or a longer summer retreat, knowing what to wear in marthas vineyard makes packing easy and keeps your look effortless from sunrise to sunset. Focus on breathable fabrics, layered pieces, and water-friendly beauty products and you’ll be ready for every vineyard moment. Want more seasonal suggestions? Check out my fashion guides and leave a comment below with your favorite Martha’s Vineyard outfit or question — I’d love to help you style your island getaway.
Ready to pack? Share this article, subscribe for more travel-style tips, or drop your wardrobe dilemma in the comments — let’s make your Vineyard trip effortlessly chic.
