What to Wear in Nantucket? 20 Outfits That’ll Turn Heads (Get Ready for #14!)

Visiting Nantucket felt like stepping into a coastal dream—quaint streets, sea breezes, and effortlessly chic style.

But I quickly learned that what you wear here matters—it’s laid-back yet polished. My suitcase didn’t exactly scream “preppy coastal” at first! 😅

If you’re heading to this charming island, here’s exactly what to wear in Nantucket to stay stylish, comfy, and photo-ready for every pastel backdrop.

1. Sailor Chic: Classic Stripes

Nothing says Nantucket quite like sailor stripes! This timeless design reflects the maritime history of the island while keeping your look effortlessly chic.

For a perfect ensemble, start with a classic navy and white striped shirt—a style that embodies the coastal vibe. Pair it with high-waisted white shorts for a fresh twist that’s both nautical and trendy.

To ensure comfort during your adventures, add some espadrilles. These stylish slip-on flats are perfect for all-day wear while exploring local boutiques or enjoying brunch by the harbor. Don’t forget a straw hat to shield yourself from the sun!

Accessorize with a chic woven tote and simple gold jewelry for that added sparkle without going overboard. This combo works beautifully for a casual day out or a lovely meal by the waterfront.

Styling Tips:

✅ Opt for natural fabrics like cotton or linen for breathability.

✅ Layer with a light denim jacket for cooler evenings.

✅ Choose a bold red lip to make your outfit pop.

This outfit is quintessential Nantucket, merging comfort and style effortlessly.

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

2. Breezy Maxi Dress for Beach Days

Maxi dresses are a wardrobe staple for any beach getaway, and Nantucket is no exception!

With flowing fabrics and vibrant prints, these dresses provide the perfect blend of comfort and style. Opt for a floral pattern or bright colors to truly capture that vacation vibe.

To complete your look, pair it with a wide-brimmed hat to not only protect your face from the sun but also add an effortlessly glamorous touch.

This hat is foldable and packable, making it a convenient accessory to have while enjoying beach walks, casual dinners, or even a scenic boat ride around the island.

Don’t forget a pair of stylish sunglasses to shield your eyes and add a dash of mystery to your ensemble.

Retro aviator sunglasses are trendy and can elevate your outfit while ensuring you stay comfortable under the sun.

For a complete beach-ready outfit, consider a floral maxi dress that not only looks stunning but often comes with pockets for added convenience.

Layer with a light cardigan for those chilly evenings when the sun sets. Choose lightweight fabrics like rayon for breathability, ensuring you stay cool and fashionable throughout your day.

With the right accessories, this look is perfect whether you’re lounging at the beach or dining under the stars!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

3. Casual Yet Polished: Denim & Blazer

For those cooler days or chic dinners, a denim-on-denim look topped with a tailored blazer hits all the right notes.

Start with your favorite fitted jeans, like these fitted jeans, paired with a classic white tee. Add a structured, tailored blazer in a light pastel shade to elevate the look.

This style strikes the perfect balance between casual and polished, making it ideal for a sunset dinner or a gallery opening.

Slip on some chic loafers for a touch of sophistication, and carry a compact crossbody bag to complete the ensemble.

Outfit Tips:

✅ Experiment with different textures (think denim and cotton) for visual interest.

✅ Roll up the sleeves of your blazer for a more relaxed vibe.

✅ Accessorize with statement earrings to draw attention.

This outfit is versatile, allowing you to transition from day to night effortlessly!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

4. Nautical Swimsuits: Retro Vibes

Dive into summer with a retro-inspired swimsuit that channels old-school glamour. Think high-waisted bikinis or one-pieces adorned with polka dots or ruffles.

One great option is the high-waisted retro bikini, which not only flatters your figure but also offers that playful yet sophisticated flair perfect for a day at the beach.

Complete the look with a light kimono cover-up for when you’re not swimming and a pair of oversized sunglasses for that Hollywood touch.

The kimono adds a layer of coverage while keeping you stylish, and the oversized sunglasses not only elevate your outfit but also provide UV protection.

Style Suggestions:

✅ Don’t forget a cute beach bag to hold your essentials.

✅ Choose swimwear with built-in support for all-day comfort.

✅ Mix and match patterns for a unique twist.

Rocking this retro vibe is sure to make waves on the Nantucket shoreline!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

5. Light Linen for a Day of Exploring

When planning a day of exploration on Nantucket, comfort is key! Linen is a fabulous fabric that allows your skin to breathe while providing that effortless sophistication.

Choose a pair of lightweight linen trousers for a relaxed fit that’s perfect for wandering around.

Pair them with a simple tank top and layer with a breezy linen shirt unbuttoned for a laid-back vibe.

This combination not only looks stylish but also helps you stay cool throughout the day.

Accessorize with a lightweight scarf for a pop of color and don’t forget about your footwear—opt for comfortable slip-on sandals that provide arch support and are easy to take on and off during your adventures. This outfit is not just practical; it’s oh-so-stylish!

This look is perfect for visiting museums, galleries, or simply wandering through the quaint streets of Nantucket. Enjoy your day in comfort and style!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

6. Essential White Dress: Timeless Beauty

Every wardrobe needs a classic white dress, especially when you’re in such a picturesque location like Nantucket!

Opt for a flowing white sundress that flatters your figure while keeping you cool during warm summer days.

This dress is not only stylish but also incredibly versatile, transitioning easily from a day at the beach to dinner in a lovely restaurant.

Pair it with a light denim jacket for those cooler evenings, ensuring you stay comfortable while looking chic. The soft denim adds a relaxed vibe, perfect for the laid-back atmosphere of summer.

To elevate your look further, accessorize with colorful jewelry, which can beautifully enhance the simplicity of the dress.

Don’t forget to add a practical touch with a floppy hat, perfect for sunny days at the beach. This hat not only provides sun protection but also adds a touch of elegance to your outfit.

With these selections, you’ll embrace the timeless beauty of a white dress while being prepared for any summer adventure!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

7. Vibrant Rompers for Playful Days

Get ready to embrace your playful side with a vibrant romper! These one-piece wonders are perfect for a day of fun and exploration while keeping you stylish.

Choose a bold print or bright color that reflects your personality, like the vibrant cotton romper, which features a trendy double-layer ruffle hem.

This option not only makes a statement but also allows for easy movement as you navigate the charming streets of Nantucket.

To complement your romper, pair it with comfortable sneakers that are lightweight and breathable.

These slip-on walking shoes ensure you stay comfortable while exploring, making them a perfect choice for busy days.

When the evenings cool down, throw on a lightweight denim jacket for a chic edge. This classic piece not only adds style but also layers well over your romper for those slightly breezy moments.

Style Considerations:

✅ Opt for rompers with pockets for practicality.

✅ Choose breathable materials like cotton for ultimate comfort.

✅ Layer with a lightweight scarf for a trendy touch.

This outfit is sure to keep things fun while you explore the beautiful sights of Nantucket!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

8. Sophisticated Jumpsuit: A Chic Alternative

For an effortlessly sophisticated look, a jumpsuit is a fantastic choice. Whether adorned with a fun print or in a bold solid color, jumpsuits can be dressed up or down depending on the occasion.

A tailored jumpsuit, such as this elegant long sleeves black and white formal jumpsuit with belt, paired with block heels, creates a stunning silhouette, perfect for a nice dinner out or a summer event.

Accessorize your outfit with statement earrings, like these large flower fan earrings, to add a touch of glamour and complete your look!

When choosing your jumpsuit, consider these tips:

✅ Opt for a jumpsuit with a cinched waist to enhance your figure.

✅ Pair it with a lightweight jacket for added warmth at night.

✅ Don’t shy away from bold colors – stand out!

Finish off your ensemble with block heels, which provide both style and comfort. This outfit radiates elegance and proves to be versatile for any occasion on the island!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

9. Playful Shorts and Graphic Tees

For those laid-back beach days or casual outings, you can’t go wrong with playful shorts and a graphic tee!

This outfit is not only comfortable but also allows for personal expression. Consider wearing playful printed shorts featuring quirky designs; they’re perfect for adding a fun element to your look while also being practical for any activity.

Pair them with a relaxed-fit graphic tee showcasing your favorite band or a catchy slogan to really express your vibe.

To complete the look, slip on some slip-on canvas shoes for effortless style and comfort.

They’re perfect for a day of shopping or heading to a beach bonfire, allowing you to enjoy the atmosphere without worrying about your feet.

Style Hacks:

✅ Tuck in your tee for a more put-together look.

✅ Play with accessories like layered necklaces or friendship bracelets.

✅ Opt for neutral colors on your tee to accentuate bold shorts.

This outfit is ideal for making a statement while keeping it casual and fun!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

10. Layered Look: Sweater & Scarf Ensemble

Nantucket evenings can be slightly brisk, making a layered look essential for staying cozy while looking stylish.

A light knit sweater, like the Irish Soft Cable Knitted Crew Neck Unisex Sweater, paired with a patterned scarf such as the Super Soft Classic Cashmere Feel Winter Scarf and fitted jeans, creates a chic yet comfortable outfit.

This sweater, made from 100% pure new wool, will keep you warm while exuding a relaxed vibe, and the scarf adds a pop of color that brightens up the ensemble.

For your lower half, opt for fitted jeans and pair them with stylish ankle boots like the Unisex Rain Boots.

These boots are not only trendy but also waterproof, perfect for navigating the coastal environment while still looking fabulous.

To elevate your look, accessorize with small stud earrings for a touch of elegance, and consider wearing your sweater off the shoulder for a relaxed feel.

This layered look is ideal for an evening stroll along the beach or dinner at a cozy restaurant, combining comfort and style effortlessly.

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

11. Floral Patterns for Brunch Dates

Brunch in Nantucket calls for something playful yet sophisticated, and floral patterns fit the bill perfectly!

A flirty floral dress, like the floral maxi dress, paired with wedges, keeps your style fresh and fun.

This dress not only offers a lovely silhouette for a brunch outing but also provides the comfort needed for enjoying a leisurely day.

Consider light, airy fabrics that are comfortable while still making a statement. To stay cozy during those cool mornings, layer with a light cardigan.

This versatile piece can easily be added or removed as the temperature changes throughout the day, ensuring you always feel just right.

To keep things stylish and practical, opt for a crossbody bag. This bag not only provides ease of movement while you sip mimosas, but it also complements your floral ensemble beautifully.

These outfit ideas will have you looking fabulous while enjoying delicious brunch bites!

Last update on 2025-07-15 / Affiliate links / Images from Amazon Product Advertising API

---

12. Vibrant Beach Cover-Ups

When it comes to beach style, don’t overlook the beauty of a vibrant cover-up!

Lightweight and colorful, these pieces not only provide coverage but also add a fun touch to your beach ensemble.

Choose a playful, vibrant kaftan cover-up that complements your swimsuit while bringing a splash of color to the beach.

Alternatively, a chic sarong is a versatile option that can be styled in multiple ways to suit your look.

Complete your beach outfit with oversized sunglasses, such as these oversized sunglasses, that not only protect your eyes from the sun but also elevate your beachside style.

Pair your cover-up or sarong with a floppy hat for extra sun protection and a chic beach bag to carry all your essentials.

Style Tips:

✅ Look for quick-dry materials for convenience.

✅ Tie your cover-up in different ways to change up the look.

✅ Don’t forget a chic beach bag to carry all your essentials.

With the right cover-up, you can effortlessly go from beach lounging to beachside dining in style!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

13. Comfortable and Stylish Sneakers

For those days filled with walking and exploring, comfortable sneakers are an absolute must!

Opt for stylish sneakers like these colorful athletic sneakers that add a pop of color to your outfit. Pair them with denim shorts and a graphic tee for a sporty, chic look.

A light bomber jacket, such as this lightweight bomber jacket, can be a great addition for an added edge, keeping you comfortable without compromising style.

Sneaker styling tips:

✅ Choose patterned or brightly colored sneakers to stand out.

✅ Wear short socks to keep this look fresh.

✅ Consider a matching cap like this matching cap to complete your sporty vibe.

This outfit is perfect for a day exploring the island, visiting local markets, or even biking along the shore!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

14. Effortless Bohemian Vibes

Bohemian styles are perfect for embracing the relaxed seaside atmosphere of Nantucket!

A flowing maxi skirt, like this flowy maxi skirt, paired with a crochet top, such as this crochet top, creates a dreamy ensemble that’s ideal for a day of wandering.

The gentle flow of the maxi skirt, combined with the airy crochet design, allows you to feel comfortable and stylish while enjoying the seaside.

To enhance your boho look, opt for layered jewelry and statement accessories that embody that free-spirited vibe.

Don’t forget to add a wide-brimmed hat, like this wide-brimmed hat, for both sun protection and style.

This versatile hat not only keeps you shaded from the sun but also adds a chic touch to your outfit.

Feel free to mix and match patterns and colors for a unique appeal. Remember, lightweight fabrics that flow with the breeze are essential for keeping cool under the summer sun.

This outfit encapsulates the earthy and relaxed vibe of summer, allowing you to fully enjoy the beauty of Nantucket!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

15. Chic Tailored Shorts for Evening Gatherings

As the sun sets, tailored shorts become a sophisticated choice for evening gatherings and outings. Consider the chic tailored shorts, which provide a polished silhouette while ensuring comfort throughout the evening.

Pair them with a stylish blouse or tank top to maintain an elegant look. Complete the outfit with chic heels for that elevated touch, allowing you to move with ease while looking effortlessly polished.

Accessorize with a statement necklace to add a hint of glamour and finish off your evening look with a small clutch.

Evening Style Tips:

✅ Choose dark or neutral colors for a more formal vibe.

✅ Opt for high-waisted styles for a flattering silhouette.

✅ Consider adding a light scarf if it gets breezy.

This tailored look is perfect for enjoying dinner or cocktails at one of Nantucket’s trendy restaurants!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

16. Cozy Sweatshirt and Leggings Combo

For those lazy, cozy days or casual outings, a sweatshirt paired with leggings is unbeatable!

Opt for a fashionable oversized sweatshirt in a fun print, like the oversized sweatshirt, to stay comfortable while looking stylish.

This crewneck design is perfect for layering and will keep you cozy. Pair it with high-waisted leggings, such as these high-waisted leggings, which offer soft tummy control and are non-see-through, making them ideal for any activity, whether it’s a brunch date or a stroll through the park.

Finish off the look with a trendy pair of fashionable sneakers for that effortless vibe. If you’re looking for a bit more warmth, layer with a stylish puffer vest and add a baseball cap for a sporty touch.

Opting for neutral or pastel colors will give you that laid-back look you desire.

This outfit allows you to stay cozy while still looking put-together, making it a versatile choice for your Nantucket adventures!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

17. Stylish Swim Cover-Up Dresses

Transform your beach outfit with a stylish swim cover-up dress! Look for flowy materials that can easily transition from the beach to lunch.

A great option is the flowy swim cover-up dress, which combines practicality and fashion perfectly. Choose a bright print or a solid color that complements your swimsuit, and you’ll be ready for any seaside adventure.

Pair your cover-up with cute sandals and a beach bag for your essentials.

Don’t forget to bring along some breathable beach accessories like a waterproof sandproof beach mat, ideal for picnics or lounging on the sand. It’s a must-have for keeping comfortable during your beach outings.

For a look that captures the essence of a sundress while providing versatility, consider the versatile sundress. It’s perfect for taking a stroll or enjoying ice cream by the shore.

Cover-Up Dress Tips:

✅ Choose breathable fabrics for comfort.

✅ Look for versatile styles that mimic sundress vibes.

✅ Don’t forget your favorite beach accessories!

This look keeps you stylish while lounging at the beach or grabbing an ice cream during your seaside adventures!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

18. Relaxed Crop Tops with High-Waisted Bottoms

The combination of relaxed crop tops with high-waisted shorts or skirts is perfect for summer in Nantucket!

This outfit creates a casual yet trendy look that can easily transition from daytime adventures to evening outings.

For a comfy and stylish top, consider the lightweight, relaxed crop top, which offers a loose fit, ensuring you stay cool during those warm summer days.

Pair it with high-waisted shorts that feature pockets for added functionality while maintaining a chic silhouette.

Accessorize with a layered necklace set to add a fun touch of elegance to your outfit.

The combination of fun prints or bold colors for your tops with complementary high-waisted bottoms will surely turn heads!

Fashion Tips:

✅ Choose lightweight fabrics to keep cool.

✅ Mix and match patterns for a playful vibe.

✅ Opt for comfortable footwear to keep the look balanced.

This outfit is great for beach days, casual dinners, or outdoor festivals!

---

19. Classic Trench Coat for Breezy Evenings

As the evenings cool down, a classic trench coat can add sophistication to any outfit.

Opt for a classic lightweight trench coat that is both stylish and easy to layer over your summer dresses or tailored outfits.

Its neutral tones make it extremely versatile, ensuring you can pair it effortlessly with different looks.

For a chic finish, consider complementing your trench with stylish ankle boots that not only provide comfort but also elevate your entire ensemble.

Layering Tips:

✅ Choose a trench with unique details like belted waists or fun buttons for an added touch of flair.

✅ Incorporate a statement piece, such as a statement bag to further enhance your style and make your outfit pop.

✅ Wear your trench over different outfits to maximize its versatility and create fresh looks throughout your Nantucket stay.

This outfit is perfect for those breezy Nantucket evenings while still looking effortlessly polished.

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

20. Sassy and Chic Skater Skirts

Skater skirts bring a fabulous sense of fun to your summer wardrobe!

Pair a colorful skater skirt, like this colorful skater skirt priced at just $16.88, with a fitted top such as the fitted top available for $6.99 to highlight your figure – this combo can take you from casual outings to more dressed-up events.

Add some cute flats or heeled sandals, and don’t forget to accessorize with a fun belt or chunky earrings for that touch of sass!

For added style on chillier days, layer with a classic denim jacket that’s perfect for $44.86. Mixing textures, like denim and smooth fabrics, can create visual interest that enhances your look.

This outfit is playful yet chic, making it a perfect choice for a night of fun with friends!

Last update on 2025-07-16 / Affiliate links / Images from Amazon Product Advertising API

---

Conclusion

Nantucket’s charm is undeniable, and with these 20 outfit ideas, you’re set to impress wherever you go!

From breezy beach days to elegant dinners, there’s something in here for every occasion.

Remember to have fun with your fashion choices and let your personality shine in every outfit you wear during your Nantucket adventures!

This post contains Amazon affiliate links, meaning I may earn a small commission if you purchase through my links, at no extra cost to you.

---

---