Since finishing up my Guide to Nantucket post sharing all of my favorite local haunts and fun things to do on the island, it’s now time to give you all insight into what I wore during my time there.
Nantucket is typically known for cultivating a preppy style: the distinguished “Nantucket Red” pants, Vineyard Vines whale print, popped collars on polo shirts, pastels and bright colors, Lily Pulitzer, Vineyard Vines, and J Crew worn head to toe in abundance, etc. Now, if you’ve been following my style on this blog or via Instagram, you know that I am most definitely not a prepster. However, I will dabble and incorporate preppy pieces that I find do fit with my personality and style if given the right opportunity. I’m never averse to trying something out if I think I can rock it in a personalized way!
That being said, I definitely felt the Nantucket prep influence during my time there and freely embraced looks that matched the flower-covered houses, cobblestone streets, and white picket fence surroundings. Whether it was a black gingham dress or a naval-inspired blazer, I played around with matching the island’s vibe and had a blast doing so!
For Main Street and Straight Wharf:
I’ve been obsessed with Nordstrom’s more recent in-house brand, 1901, since it first came out. These pieces are just so classic and I can’t get enough. I absolutely adore this seersucker dress (similar) and wore it a few times during this trip. This particular instance was when I styled it down for strolling around town and along the wharf.
For traversing the Sconset Bluff Walk:
There is nothing more iconic about island dressing than wearing Nantucket Red. This faded pink denim material has been a staple here forever and you can browse the full line of Nantucket Red apparel at Murray’s Toggery Shop on Main Street.
That being said, I donned my trusty Nantucket Red skirt, a cute t-shirt paying homage to the island’s biking culture (similar), a simple boater-style panama hat, and some low heels good for walking around Sconset (similar). I brought an old Zara jacket (similar) that I’ve had for years just in case the grey skies brought in cooler weather (they did). I’m used to walking around the paths of Sconset and Sankaty Lighthouse, but I would recommend flat shoes or sneakers for anyone unfamiliar with the terrain, as it can get very sandy, hilly, and filled with plants.
For lounging on Madaket Beach:
This fun striped two-piece from Aerie has retro vibes that I adore! It was just too cute to pass up. I also love supporting brands with positive messages, so I couldn’t wait to snag my first Aerie bathing suit and give back to a brand that promotes self-love and body-positivity! Here are links to the top and bottom in different colors.
For Upscale Dining:
I dined at two beautiful, fancier restaurants on Sunday and Monday night: Toppers at The Wauwinet and Galley Beach, respectively. For each of these dinners, I took a simple, preppy staple such as my aforementioned seersucker dress and a plaid midi dress (also from 1901 – here’s the fall version) and jazzed it up with rose gold heels, elegant statement jewelry, and a touch of makeup. Nantucket style is never flashy, so I tried to keep my looks as classic as possible.
For Casual Dining:
Although I’d honestly have been fine going out in nice white jeans and a cute blouse to most restaurants, I did want to update my more casual evening looks. This navy 1901 midi dress was the perfect option, with a thicker material for cool nights, elegant color that made it easy to dress up or down, and button detailing that paid homage to the island’s nautical history.
Island Vibes in General:
Back in my Nantucket Reds, a simple striped tee, panama hat, and some cute flats, I was completely in my island element! This look just screams “Nantucket” to me and I wouldn’t have it any other way!! I wore this outfit to hit up some of my staple spots (The Brotherhood for lunch, walking through the Jared Coffin House, and snagging some Sweet Inspirations treats to bring back home) on our second to last day on the island.
I hope you all appreciated these two Nantucket posts – I had a blast writing about my favorite island! Let me know your favorite places to travel in the comments!