There are two versions of me: the New Yorker buried under a hat and scarf, and the Florida Gator who thrives under the southern heat (though the latter usually only exists in my mind, thanks to online grad school). This January, the Gator made a public appearance thanks to a whopping 82-degree forecast during a road trip that had me ditching the winter gear for some serious outfit planning. Even though Florida weather requires some strategic pivoting, I had the best time putting these looks together. Outfit planning is one of my love languages, after all. Without further ado, here is my January 2026 style diary from the road.
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Day 1: 7 Brew Run & Outlet Shopping
No Boundaries Plush Half-Zip Pullover, Teddy Bears | Walmart
High-Waisted PowerSoft Full-Length Pocket Leggings, Black Jack | Old Navy
Day 2: Errands & A Beach Sunset
No Boundaries Ribbed Crewneck Tee with Long Sleeves, Ivory Floral | Walmart
501® Curve Women’s Jeans, Cold Summer | Levi’s
Trailblazer Sneaker, Sand Beige | Ryka
Purple Myrtle Beach Full-Zip Hoodie
Day 3: First Visit to the University of Florida
Stretch Terry Blythe Jumpsuit, Riverton | Faherty (Original)
Day 4: A Morning on UF’s Campus & A Disney Springs Afternoon
Long-Sleeve Slit-Neck Ruched Top, Thimble Berry | Old Navy
501® Curve Women’s Jeans, Lucid Dream | Levi’s
Kitsch Rabs Zig Zag Recycled Headband – Black/Tortoise – 2pk | Target
Day 5: Cape May Cafe, Disney Springs & SeaWorld Orlando
Walt Disney World Attractions T-Shirt (On-Property Exclusive)
Day 6: First Visit to Epic Universe
HomeStretch™ Rib Tune T-Shirt, Medium Pink (Discontinued Shade) | Aritzia
Women’s High-Rise Cinch Baggy Jeans, Capturing Moments | Levi’s
Day 7: Epic Universe (Part 2)
Day 8: Three Universal Parks, One Day
Day 9: Road Trip Home
Day 10: Bonus Adventure at Hershey’s Chocolate World
Women’s Snoopy and Woodstock Heart Graphic Pullover Sweater | Target
Natural Reflections Highland Pocket Leggings | Bass Pro Shops
Kitsch Rabs Zig Zag Recycled Headband – Black/Tortoise – 2pk | Target
Accessories
Luna Classic Aviator Sunglasses, Milkyway | Free People
Vera Bradley Crescent Bag (Discontinued)
While my Super Puff was inevitably waiting for me back home, getting to play the part of a full-time Floridian for a week was a much-needed reset. Whether you’re a fellow Gator, a cold-dreading New Yorker, or just someone who treats their suitcase like a curated art gallery, I hope these looks gave you some inspiration for your next getaway. Which of these fits was your favorite? Let me know in the comments! I’m definitely not asking to distract myself from two weeks straight below freezing…
