What to Wear in Highland Park

Highland Park rewards restraint with one rich detail, so the pieces that work here are the quietly confident ones. A shirt dress in an original print handles the Village by day. A tailored set reads polished at a luncheon without trying. And for dinner, a draped goddess kaftan brings the drama in the fabric, not the styling — exactly the note this neighborhood likes. It helps that every print is original artwork designed in-house, so what you wear isn't on a rack at the mall; it's the kind of refined-but-not-loud piece that earned Sai Sankoh D Magazine's Best Resortwear in 2024.

Half the pleasure of dressing for Highland Park is having somewhere to wear it. Lunch at Bistro 31 in the center of the Village — the Lombardi family's French-Italian room, with a covered patio made for a long midday table — calls for a printed shirt dress or a tailored set. For dinner, Honor Bar sits under a sweeping oak just steps away, easy and grown-up, the kind of place a goddess kaftan and a good earring feel right at home. Make a night of it at the Rosewood Mansion on Turtle Creek — the original Rosewood property, on a terraced hill minutes from the Village — where The Mansion's dining room is worth a floor-length moment.

It's a neighborhood that rewards getting dressed. Brunch the Village, shop the boutiques, and let one beautiful piece carry you from the patio to the dinner reservation.