Boots With Relaxed Attitudes
A soft and slouchy boot is equal parts easy to wear (a wider shaft means your calves won’t be confined to rigid, sometimes sweaty leather) and easy to style. They look incredibly sophistiated paired with cute winter dresses (Brandon Maxwell’s Resort 2025 edit offers plenty of inspiration for this specific styling) or with cheeky Bermuda shorts and an opaque tight à la Chloé’s bohemian beat.
A No-Frills, No-Fuss Loafer
The best loafers will always be a footwear staple—to call the preppy style a shoe trend would be like announcing that the sky is blue as breaking front-page news. But winter 2025 narrows in on one specific loafer silhouette: sleek, anti-chunky, and low-to-the-ground pairs made of soft black leather. As far as winter loafer outfits go, feel welcome to express all parts of your wardrobe, from buttoned-up and preppy to downtown edge.
Cole Haan Women’s Geneva Loafer
Ground Point
We’ve seen ample iterations of ballet flats in recent seasons. Mesh and sheer ones, schoolgirl strappy ones—and now, sleek ones that come to a sharp point. They were a clear designer favorite, with brands like Givenchy, Stella McCartney, Burberry, Max Mara, and Ulla Johnson all favoring a triangular shoe. Plus, a pointed-toe flat is the peek-a-boo shoe, peering out from maxi hems or baggy denim.
