Fashion: Taking On Nantucket Wine Festival One Style at a Time

Nantucket Wine Festival is an annual island highlight taking place every third weekend of May. A mature crowd flocks to the festivities surrounding the festival that brings winemakers from around the world, along with top notch chefs, to an extra long weekend focused on food, fashion and of course fabulous wine. Here’s a style-guide to help you pack your bags full of looks you’ll love when you’re headed to Nantucket’s next Wine Festival.

Island dwellers come prepped to the nines in brightly colored Lily Pulitzer attire easily found at just off Main Street’s, In the Pink and a bit more trendy, but just as colorful, recently opened Shift. Men tend to get in touch with their Vineyard Vines side; dressing in seersucker, salmon, colorful pants and prints you don’t often see in big cities.

Those from off-island may find it hard to find attire that works for the variety of events they plan to attend and treads the line between island fashion and personal expression.

If you find yourself flustered and shopping without finding something that works for you stick with what you know and love.

Surprisingly enough the most compliments came while wearing a pervious season’s BCBG maxi dress (in the featured image of this post) paired with a gap denim jacket. A huge hit with shop owners, wine fest attendees and friends found along the streets; I tossed this go to outfit in my bag last minute when nothing felt quite right while shopping for new special pieces.

Another simple and timeless piece that turned heads was a cream colored boho shift dress with lace detail; paired with the same demin jacket and wedges from the day before, this easy to pack, not in need of ironing staple transitioned from day to night without a hitch. The combo of these comfortable “just me” pieces that I often toss on at home made big waves at Nantucket Wine Festival.

Rocking the same seersucker blazer and an alternating selection of t-shirts with light-weight pale gray and navy pants, my husband fit right in. His navy Lacoste boat shoes pairing with each look and adding a prepped up edge to his regular look that allowed him to still be comfortable.

However, there’s one event you should put a bit more thought into, the Gala. This kick-off to the festivities takes place Thursday evening at  White Elephant Hotel’s Brant Point Grill and spills onto their lawn.The Gala sets the mood for the weekend, and introduces guests to what’s to come, offering an endless sampling of food and wine, this cocktail party is the most difficult event to dress for. The word gala implies a need for cocktail attire if not black tie, but on Nantucket things are little more laid back, and the combo of cobblestones and expansive lawns will leave you teetering on high heels.

Slightly overdressed for the Gala
Slightly overdressed for the Gala

Donning a black Monique Lhuiller knee length dress, paired with a Nantucket- esque bright green statement necklace and a pink pashmina, I felt confident that I’d fit in among a sea of revelers who embraced all aspects of fashion. And I did, falling somewhere in between the formal and casually dressed (some in sequenced gowns, others more casually elegant in trousers).

Men were dressed in everything from suits with ties to jeans and sneakers. The best looks on the men in attendance were from those who wore a suit or blazer and slacks and opted to go tieless.

Next time, I’ll put together a look that’s a bit less fancy and go for something a little more flouncy like this J Crew  fit flare in a bright color, and for sure I’d pair my dress with wedges to add height to my 5’1″ frame. I’ll let my hubby leave the tie behind in favor of a print button down to sport under his blazer.

As for a purse, this is true cocktail party with little bites you won’t want to miss doled out by top chefs from Nantucket, Boston and beyond and paired with wines served by winemakers from around the world. Make sure your evening bag has a handle so you can enjoy every sip and nibble sent your way.

Then feel confident that you look fabulous because how you feel is what really matters when you’re at Wine Festival or anywhere.

-Reminding you that fashion only makes sense when you feel fabulous, Jess

Have you been toNantucket Wine Festival? Share your favorite fashion  photos with us at Amazing Matriarch on Facebook: Amazing Matriarch, Instagram: amazingamtriarch or Twitter: @AMatriarch;  Tag us using#amazingmatriarch. 

Armed with an undergraduate degree in Marketing and a Master’s Degree in Teaching, Jessica began a career as an advertising executive before spending nine years as an 8th grade English teacher. In 2009, Jessica opted out of the workforce to be home with her kids. In need of an intellectual outlet, Jessica was offered the opportunity to start a third career as a freelance travel & lifestyle writer and has never looked back. Having contributed to travel & lifestyle outlets: Nile Guide, Tripology, USA TODAY & 10Best Jessica is excited to be part of the Amazing Matriarch where she hopes she can encourage other women to channel the amazing within.

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