I used to do a series back in the day on Wednesdays where I would put together a virtual outfit. Last summer I shared this post, which was pretty close to that concept, but this time around I am thinking it might be fun to take it a step further and curate a look with a specific intention or location in mind. As we have been packing our bags to head out on very limited family visits the last couple of weekends with our little one I have been putting an overwhelming amount of thought into each outfit I pack. I haven’t seen anyone in a year, can you blame me? I also may have forgotten how to dress myself between pregnancy and becoming a mom but that is a different story.

Coming up we are planning to take a day trip out to the East end. On my list of musts are stopping in at our favorite winery and picking up a pie from Briermere. An outdoor lunch would be a nice bonus, and a quick stop for coffee too. I am such a fan of drive through coffee stops when we’re out in the suburbs, even if we end up going in most of the time anyway. I digress.

For a day of wine tasting on the North Fork I like to keep things casual but transitional in the event that we linger for dinner.

01. Top – Love the smocking on this top, and the ties. Every element is perfect and I would love to add this one to my closet asap! — 02. Sunglasses – You can never go wrong with a classic pair of black cat eye sunglasses. — 03. Shorts – This pair of denim shorts is a recent purchase for me. I wanted something with a wider leg and longer length and these hit the mark. I recommend sizing down as they are 100% cotton and stretch out pretty quickly. — 04. Necklace – Lately I have been very into initial and name jewelry. I love this pearl initial pendant, the pearls add such a sweet touch. — 05. Cardigan – Another thing I have been very into lately is florals. The daisy stitching on this cardigan is the sweetest detail. This cardigan seems to make it onto my wishlist each season as different patterns are released, they are always so good! — 06. Bag – I’ve been on the lookout for a cute straw bag for Summer and this one is currently in my cart. The design with the canvas liner is just perfect, even if I’m currently more of a diaper backpack girl, ha. — 07. Bracelet – When it comes to jewelry I tend to wear the same dainty pieces every day, but in the Summer I love adding more fun pieces to the rotation, especially when it comes to bracelets. The woven detail and beaded trim on this one is so cute! — 08. Sandals – I have been eyeing this pair for a year and love how they can be dressed up or down. A sandal that can be paired with both casual and more dressed up looks is always a win in my book!