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"I don't know how to say goodbye." ~ Princess Ann to Joe Bradley in Roman Holiday

When I first saw Roman Holiday years ago in high school, I recall being particularly taken by the ending of the movie. While much of the now iconic scenes filmed in and around Rome are undeniably joyful, it's the realization both Princess Ann and Joe Bradley come to during the final scenes: that being their paths will never cross again, that struck me the hardest. Her world -- of royal standing -- and his -- of the American press -- two seemingly opposite orbits that collide for one fateful joyride all around Rome. Enjoying gelato, riding Vespas and dancing well into the evening hours along the Tiber River -- the two enjoying a day of childlike delight, neither eager to share who they really are with the other person, but instead, reveling in their anonymity for just a few hours more. Because they both know it'll end all too soon.

Since that day, I suppose you could say Roman Holiday made me fall in love with sad endings. In fact, I'll go out on a limb here, and say I think I much prefer love stories that end this way (Casablanca and La La Land are other great examples of this). Don't get me wrong, I'm a sucker for a good ol' fashioned love story with the glowing sunset that the happy couple rides off into. But 9 times out of 10, I find there's something much more human, more relatable and more palpable about a love story cut short. It's a testament to unrequited love. The kind that doesn't require Shapespearean proportions of death and betrayal, but rather a story of two people who, despite their best efforts or the circumstances they can't control, need to let each other go. It's a heavy-hearted goodbye but one wrapped in the warm thought that someday, you'll think back fondly to those memories with that other person, and hope they're doing well.

I like to think we all have previous love stories like Princess Ann's and Joe Bradley's -- and hopefully, these images pay tribute to the glow those memories hold in our hearts, years after those people leave our lives.

Stay tuned for part 2 of our Roman Holiday editorial coming tomorrow. And in the meantime, be sure to check out the rest of our TTT Classics series right this way: Funny Face, Grey Gardens, Casablanca and The Notebook.

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OUTFIT DETAILS: On Krystal: Frank & Eileen top (gifted, sleeveless version here) // ARoss Girl X Soler skirt // Sarah Flint sandals (gifted) // Vintage scarf // Poolside bag (gifted) On Igee: Institchu suit // Drake's tie // BM Franklin hat // Paul Evans shoes // Indochino shirt

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Photos by Grant Legan // Featuring my handsome friend Igee Okafor