Casual Friday, but make it feel intentional. Everyone’s talking about 2016 style lately, but this outfit took me straight back to the early 2000s — in the best way. I started with an oversized men’s polo with bold graphic branding and rugby-style striping. Very Y2K, very throwback. I chose a medium tall so the length and scale felt deliberate, not just “borrowed.” A slight front tuck helps define the waist without fighting the oversized silhouette. The jeans are a loose, straight-leg boyfriend fit from a tall brand — intentionally relaxed, mid-rise, and honestly some of the best-fitting jeans I own. The rise actually hits where it’s supposed to (rare), and the inseam is long. I’m 6’3” with a 36" natural inseam, and these are long enough that I cuff them — or could easily wear them uncuffed if I wanted even more length. I finished the look with a small cuff, shearling-lined booties for a cozy, casual-Friday feel, and a belt that’s actually from the early 2000s and still fits (a small personal win). Simple jewelry, plus a styled bobby pin and deep side part to fully lean into the Y2K energy. Relaxed, nostalgic, and very wearable. 👉 Comment SHOP for links + fit details. LTKPlusSize LTKMidsize LTKTall