Fashion Moments

An OOTD Moment – Lilly Pulitzer You Gotta Regatta

Hi everyone!


Outfit Details: Shep Shirt (Similar) / Shorts (Sold Out! Same style, different pattern) / Boat Shoes (Similar)

The best clothes are always the ones that come with a story behind them. That’s the case today with pretty much the entire outfit.


After I was finished with my internship in New York, I spent approximately eight hours home in Pittsburgh before piling in a car again to head to Washington D.C. for vacation over the 4th of July. Now, I don’t know if it was scatterbrain from having just packed to leave New York or the fact that it was a scorcher the last time we visited DC for the holiday, but I only packed for 90 degree days. It didn’t even occur to me that I should probably check the weather.

Needless to say, it rained most of the time and was relatively freezing for summer. Especially on the 4th. I had a spaghetti strap dress on and spent most of the day talking myself in and out of buying a $50 sweatshirt from the gift shops.


As it was torrentially raining outside and we were trying to decide whether to stand in it with the chilly wind for two hours to catch the fireworks, I remembered that I had purchased this Shep Shirt from Vineyard Vines in Georgetown a couple of days ago. This sweatshirt pretty much saved my life that day. I looked like a fool though with this pulled over my dress, I will admit. But I was warm and happy, so that’s all that matters.


Now these shorts are another story. When Lilly Pulitzer announced that their beloved pattern ‘You Gotta Regatta’ would be re-released, it was pretty much madness. This is probably their all-time best seller and can go for crazy prices on eBay. So I was pretty stoked that they were coming back with some new pieces in such a classic print.

THEN Lilly announced that they were debuting the print earlier than the online launch in one location only: the Lilly Pulitzer store on Madison Avenue. I was still in New York at the time and was thanking my lucky Lilly stars.


But, I had already visited the store the weekend before (obviously) and spent a sizable/embarrassing amount of money. So the day of the launch, I sat in my internship in Lower Manhattan arguing with myself over whether to take a train ride to the Upper East Side and hand over another chunk of change or not.

Ultimately I decided to throw caution to the wind and flex my credit card. I hopped on a 6 train and went about four stops until we, well, stopped. If there’s anything I learned in New York, it’s that public transportation is unpredictable and a little unreliable. I sat at the same stop, pretty much trapped unless I wanted to walk thirty blocks, for nearly a half an hour.

Seeing as it was already after 6:30, I was racing the clock to get there by the time they closed at 8:00. I’ll save you the suspense – we eventually started moving, I secured both these amazing Addie shorts AND a romper in the pattern and I took a fairly empty train home.


These two pieces, I think, work really well together and would be perfect if you were actually going out on the water. The closest I got to that today, though, was watching my neighbors do some repairs to a boat that magically appeared in their yard this morning. Hooray.

What are some stories behind your favorite clothing pieces?

Thanks for reading!

xoxo Rebekah

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