Despite the fact that I am very much a dress girl, I do love a good midi-skirt. It's the perfect transition piece when the weather is warm-ish in the afternoon and chilly at night. Add a denim jacket, and you're really set for those colder North Eastern Spring nights.

Outfit Details: White Tee (also love this one), J. Crew Midi Skirt (similar here), Free People Jacket (similar longer version here, vintage Dooney & Bourke Bag (similar here)

When it comes to traveling/packing, I get a serious case of FOMO. I envision tons of scenarios: what if it's cold, what if it's raining, what if it's muddy. The list goes on and on. I even envision scenarios that would literally never happen, like what if I go rock climbing. Regardless, all of these "what ifs" include a "well I NEED a cute outfit." The solution: versatile pieces, like a midi, that can exist in all my imagined scenarios. My favorite J.Crew Polka dot midi (similar here) fit the bill throughout my trip to Santorini, perfectly paired with a wine tour and some baklava.

Since Greece has been on my list of dream places, I knew there were several things I wanted to do: sail around the island, visit wineries, eat all the things, and just relax. We were lucky enough to book a wine tour to three different, breathtaking wineries. Since it was off season, the tour only had one other couple. It was perfection, and my midi was the perfect staple for the day: comfy, but dressed up.

Note: This photo was taken at the just the right moment. I may or may not have been winding up to do what every girl does in the perfect skirt or dress: twirl!

Mix and match midi skirts with tops and blouses. From a plain white tee (like I rocked in Santorini) to different patterns. There is a great selection of midi's at Madewell (plus tons of cute basic tee's) and Nordstrom. Happy Shopping!