Preppy Outfits Diaries

Preppy outfits to reflect May 2026 were truly super fun to style and dress for, as it was month filled with Birthday celebrations to ring in year 27, a long weekend with some of my closest friends, and several collaborations and work-related events as a full-time blogger. May 2026 was, as I say probably just about every month, truly one for the books! I felt so loved by all of my friends and family members that came together to celebrate Chapter 27 as well as excited for all of the work-related events and collaborations I got to execute and take part in, too. Truly, I feel extremely grateful! At the same time, it was super fun to document and dress up for alllll of the fun occasions during May 2026.

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For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. For my outfit archive, look no further than My Preppy Outfits Archive.

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Preppy Outfits Diaries – May 2026

My Favorite Pieces

May 2026 was a cooler-than-usual month in the Washington, DC area, so all of my preppy outfits this past month reflected that. I enjoyed styling several fun preppy outfits, including some fun Spring/Summer knits like my pink American Flag sweater that I received as a part of a collaboration with Top It Off Accessories (which you can receive 20% Off The USA 250 Collection Item at Top It Off Accessories with code KATIE20), as well as my gingham rain jacket that I snagged before it went out of stock from J Crew Factory. I also enjoyed styling some fun midi/maxi dresses with cardigans and quilted jackets and some fun loungewear, too!