Preppy Outfits Diaries - June 2026

From Summer in Italy to Americana back at home, June 2026 was definitely one of my most memorable months to date – preppy outfits and memories, alike! To kick off the month, I hopped on a Transatlantic flight to Europe to celebrate my college roommate’s wedding and spend 12 incredible days under the Tuscan sun in Tuscany, Italy. Then, I came home and started celebrating all-things America 250 as the festivities kicked off locally. Overall, I have had such a fun month and start to Summer 2026!

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Preppy Outfits Diaries – June 2026

My Favorite Pieces

Styling outfits for both Italy and America 250, there has definitely been a mix of my favorite pieces for June 2026’s preppy outfits. Whether it be my go-to travel shoes and travel tote or my go-to Summer sandals and Summer crossbody, June 2026’s preppy outfits consisted of a lot of the same accessories being styled throughout the month.