Living on Nantucket isn’t always picture perfect. Sorry, let me take that back – Nantucket may always look picture perfect, but living on an island isn’t always such a breeze. But there is no better time to be on this little elbow of sand than at the holidays. If you’ve never done an ACK-cursion between Thanksgiving and New Year’s, then you’re missing the most positively idyllic combination of a Norman Rockwell painting and Stars Hollow (yes, I’m on a Gilmore Girls kick right now – I actually never watched the entire series so I’m trying to catch up now before “A Year in the Life” comes out!).

One of the most magical times of year is Christmas Stroll, which is the first weekend in December. Trees decorated by local businesses line Main Street, Santa Claus arrives via Coast Guard boat to greet the kiddies, and everyone’s merriment literally exudes out of them in the form of silly holiday hats as they peruse local shops and eateries. It’s a bit crazy, but an ideal weekend for festive fanatics.

It probably comes as no surprise, but dressing for a theme gives me life. Stroll is a tough one though, given New England’s finicky and inconsistent weather. Plus most of the “summer people” return so everyone is dressed to the nine’s in holiday garb. So I was so excited when my friends at Shift asked me to put together a few ensembles to get a girl through the bevy of seasonal gatherings. I have been a fan of Shift since I first laid eyes on their Main Street location two years ago when they graduated from their space at In the Pink. My husband actually scored me two amazing dresses there at an end of the year sale last year (like this all-purpose number that I wore to Easter, Nantucket Wine Festival AND the Boston Pops concert) and their window displays this summer have been making me do a 180 every time I walk by.

My first look is all about a casual and comfy ensemble for said Stroll weekend activities. For me, it’s usually hanging out on Main Street to observe the festivities, but if you happen to live not on a magical holiday island, it’s still the perfect outfit for Christmas shopping, a holiday brunch, or when you want to feel like it’s socially acceptable to walk around wrapped in a cozy blanket.

Seriously, this plaid poncho is everything my lazy dreams are made of. Also these black pants are actual pants (like with zippers and an inseam and everything) but feel like leggings. Meaning I could take them from Sankaty to downtown and be comfortable all day long. Also I’m kind of obsessed with this white and gold chiffon top – it’s one of those versatile pieces that could be worn with a pencil skirt for work, jeans for casual but dressy night out, or layered up for an adventure like I did in ‘Sconset.

And that hat? Totally worth holding onto a windy Nantucket day. It comes in camel too!

If you want to get your hands on any of these pieces, visit Shift on Main Street – they’re open now through Stroll weekend! (For their full hours, check here or call.) See below for full outfit details.

And as a special offer for my readers, Shift is offering you lovely people a 10% discount! Just mention Lindsay’s Look to receive this discount off your in-store purchase.

I’ve got two more holiday looks coming your way soon, one including the most fun dresses I think I have ever worn! Stay tuned for more 🙂

And a huge thank you to my friend and blogger Molly for snapping all these photos for me. Make sure to check our her new blog Trust in Your Wanderlust here for lots of travel inspo!

Outfit details (all available at Shift!): Mudpie Hudson Plaid Ruana / Sail to Sable Metallic Chiffon Long-Sleeved Blouse / Kut from the Kloth Mia Toothpick Skinny / Cheveux Leather Band Wool Felt Hat

Additional pieces: JustFab Bag / Dolce Vita Booties via Nordstrom Rack / KJP Earrings / Charming Charlie Zodiac Ring / Target Sunglasses

This post was created in partnership with Shift. All opinions are my own. Thank you for supporting the brands that support Lindsay’s Look!

~L