Fall outfit work office chic

If you love the old money aesthetic but want to keep it casual and wearable, this one's for you. These 20+ outfit ideas bring together timeless staples like tailored shorts, relaxed trousers, crisp button-downs, chic dresses, and structured skirts—all paired with loafers, low-key sneakers, or ballet flats for that quiet luxury vibe. Whether it’s spring brunch, a summer stroll, a fall workday, or a winter city look, these outfits are polished without trying too hard.

From the Puzzle to the Lady Dior, we've edited a definitive list of classic designer handbag brands and the arm candy that cemented their timelessness.