Hey, everyone. It’s Bobby here, the executive shopping director at Who What Wear. Today, you can also call me your personal stylist (no payment or appointment required), as I’m sharing a mix of shopping and styling with an edit of fall outfit ideas I put together from Shopbop. FYI, the big fall sale ends today, October 1, and you can take 15% off $200+, 20% off $500+, and 25% off $800+.

These forward-yet-versatile pieces work seamlessly with the full outfits below or can mix into your existing wardrobe. Think directional outerwear and pops of color. I know I’m the one who put together the looks, but in my opinion, each vibe is giving “I’m the chicest in the room.” Keep scrolling for more.

You can’t deny the power of a high-neck leather jacket—instant coolness. Add detailed jeans, an of-the-moment quarter-zip sweater, and printed flats, and you’re set.

Consider this ensemble for something modern yet elegant. A trench brings the polish, and a scarf sweater brings the glamour.

I’m feeling this layered vibe with the turtleneck underneath the corduroy button-down shirt. The coordinating pink pants are also relevant.

Go for it this fall with a statement coat and pants! To balance out these pieces, the simple long-sleeve top and boots feel right.

A rugby polo is a fall 2026 staple. Style it with utility jeans, trendy oxford flats, and fun accessories.