We Broke Down Oprah’s Casual Cool Fall Outfit Piece by Piece

Welcome to The Blueprint, where we break down the celebrity looks we want to wear right now and build them back up, piece by piece.

I’m adding Oprah to the list of my 2025 fall fashion muses. 

Yesterday, the media mogul shared some BTS photos of her time truffle hunting in Italy. While I have no plans to travel or truffle hunt anytime soon, I did intend to find smarter, more functional wardrobe pieces in the coming weeks. (I’m sick of buying things that I think I’ll wear, but never actually do!) That’s why the media mogul’s unfussy polo shirt, adjustable paperbag pants, and white sneakers inspired me to copy her look. 

Oprah’s Outfit Blueprint 

Willit Wide-Leg Pants

Other celebrities like Meghan Markle also wear paperbag pants. The removable belt on these means I could tighten or loosen them depending on how much I eat, where I’m at in my cycle, and so forth. The wide-leg silhouette also still looks polished for work and won’t squeeze my legs (my fashion pet peeve). The khaki hue goes with all sorts of color families, so they match everything including polka-dots and fun prints. 

Amazon Essentials Polo Shirt

Polo shirts used to remind me of my old school uniforms, but now all I think of when I see them is Jennifer Garner, Victoria Beckham, and all the other A-listers doing their best to bring them back. I finally see the appeal, too: They’re not restrictive like starchy blouses, but they have a more formal feel and look than plain ol’ T-shirts. This one is especially “soft and cool,” according to one shopper, and doesn’t shrink in the wash — which I love to hear. 

Sernial Tennis Shoes

There are very few occasions where white tennis shoes haven’t served me well, so I’ll never complain about buying more. These are under $25, which makes me feel less guilty when I inevitably dirty them up past the point of cleaning, and made with faux leather, which I’d gladly opt for over more breathable canvas in the fall and winter.

Keep scrolling to shop more paperbag pants, polo shirts, and white sneakers inspired by Oprah now. 

Iwollence Wide-Leg Pants with Adjustable Knot 

Lillusory Wide-Leg Paperbag Trousers with Removable Belt

Magcomsen 3-Button Polo Shirt

French Toast Stretch Pique Polo Shirt

Vepose Fashion Sneakers