Restaurant Week is officially upon us! Our restaurant critic, Todd Kliman, has tips on where to dine, but now comes the more important question: What to wear to eateries you don’t normally frequent? If you plan on indulging on more than one occasion—and please consider this our official blessing to do so—a smartly selected dress will fit into a range of atmospheres. Stick to solid colors with interesting details—we like Alice + Olivia’s pleated Polly silk-chiffon dress ($365)—and pile on the accessories.
Out With the In-Laws A fancy dinner out on his parents calls for a more conservative look—stick a crisp collared shirt under your sheath, then decorate with an Art Deco locket. Classic Mary Janes and a chain-link belt keep in line with the classic feel.
Lunch With the Girls What better excuse for a good meal than catching up with old friends? Dress down, then hit a Restaurant Week lunch special—$20.10 for three courses—at a more casual spot. A light floral scarf hides a conservative neckline and adds color, while two-tone, high-top saddle boots are a fun fall trend ready to take off.