Gorgeous silhouettes and stunning prints are more than buzzwords in New York’s fashion circles; they are a daily uniform. For Tessa Faye O’Connell, a seasoned fashion insider and global PR director at Coach, dresses are the quiet heroes of a hectic city life. Between school drop-offs, showroom appointments, and late-night events, she relies on a rotation of pieces that slip on in seconds yet look meticulously considered.

O’Connell’s philosophy is simple: a dress should match your mood and your calendar. For after-work drinks or birthday dinners, she leans into romantic drop-waist silhouettes that skim the body and move with the wearer. These pieces, often in airy cottons, are easy with flat sandals by day and strappy heels by night, proving their cost per wear season after season.

Prints are where she lets loose. While her winter wardrobe skews neutral, summer in New York calls for exuberant boho florals and embroidered details that echo the energy of the city’s streets. Labels known for breezy, vacation-ready patterns are her go-tos, especially when the humidity rises and structure feels stifling.

Fabric choice is crucial. Silk and lightweight viscose offer polish without sacrificing comfort, particularly in long-sleeve cuts that transition seamlessly from over-air-conditioned offices to sweltering subway platforms. Gingham, once reserved for picnic blankets, becomes a city staple in tailored sundress form, striking a balance between playful and refined.

Not every hero piece is loud. O’Connell swears by the power of a perfectly cut black T-shirt dress, a blank canvas that works with a blazer and pumps for meetings or a denim jacket and sneakers for weekend errands. Similarly, white dresses are nonnegotiable in her summer lineup, their crisp simplicity elevated with a tan, gold jewelry, and a reliable SPF.

Texture-driven trends also have a place in her closet. Crochet dresses nod to beach holidays yet feel modern in streamlined shapes, while nightgown-inspired styles bring an off-duty elegance that reads intentional rather than undone. Slip dresses, meanwhile, remain indispensable: layered over tees, under blazers, or worn solo for evening, they offer endless versatility.

Shirred bodices and lace details round out her edit, delivering comfort, stretch, and a touch of romance. For O’Connell, these 11 dress trends aren’t fleeting fads; they are the building blocks of a wardrobe that keeps pace with New York—and looks beautiful doing it.