What to Pack for Five Fall Getaways

For men

Sportif classics like a lemon-rind polo or a pair of linen shorts bring an old-school charm to the tennis tournament of the year, while a classic sweater by fashion wunderkind J.W. Anderson at Loewe is a smart investment for fall.

Loro Piana shorts, $445, loropiana.com.

Loro Piana leather and denim backpack, $2,450; mrporter.com.

Rolex Yacht-Master II, $18,750; rolex.com.

Bally leather sneakers, $450; bally.com.

Lesca sunglasses, $255; nomanwalksalone.com.

Caruso polo shirt, $385; thearmoury.com.

For women

Sure, the U.S. Open might begin at the end of August, and as such, you might beg the question, "Won’t my summer wares do?" But natty additions like a checked blazer and a newsboy cap will not only take you from Arthur Ashe to an evening cocktail in Manhattan, but prove versatile as the weather begins to cool off come September.

Thom Browne cashmere sweater, $1,690; mytheresa.com.

Marsèll suede tote, $1,395; farfetch.com.

Dior leather handbag, price upon request, dior.com.

Golden Goose suede-paneled leather sneakers, $480; net-a-porter.com.

Larkspur & Hawk Rhodium-dipped, quartz and pearl earrings, $1,550; net-a-porter.com.

Prada leather-trimmed wool blazer, $3,190; net-a-porter.com.

Roberi & Fraud sunglasses, $240; barneys.com.

Chanel cap, $800; chanel.com.

Esme Vie cotton dress, $1,895; modaoperandi.com.

For men

With Haider Ackermann at the helm, Berluti’s crisp lines and sumptuous fabrics have never looked better. The Italian house gives the classic tuxedo a hint of drama in a moody, ink blue velvet—just the thing for an evening at the annual gala celebrating the opening of the ballet. Pair with double-monk strap brogues by Gucci, a thin cashmere sweater, and finish with a clean, Neroli-scented shave.

Berluti velvet jacket, $4,520, and trousers, $1,130; berluti.com.

Gucci monk shoes, $980; gucci.com.

Tom Wood silver and marble ring, $400; tomwoodproject.com.

Ermenegildo Zegna cashmere sweater, $695; mrporter.com.

Aesop Moroccan neroli shaving duet, $80; aesop.com.

T. Anthony leather garment carrier, $1,300; tanthony.com.

For women

Haider Ackermann’s well cut suiting isn’t just for the gents—the designer’s namesake line made a sultry peak lapel dress for fall that borrows from the boys gracefully. Round out your weekend wardrobe with feminine touches like a slip dress, a day-to-night bag, playful denim, and a luxe knit.

Haider Ackermann satin dress, $1,318; matchesfashion.com.

Tabitha Simmons velvet embroidered heels, $875; tabithasimmons.com.

Valentino denim culottes, $990; valentino.com.

Prada velvet bag, $1,850; net-a-porter.com.

Margot slip dress, $1,050; modaoperandi.com.

Rejina Pyo sequined top, $754; mytheresa.com.

Simon Teakle antique diamond earrings c. 1850, price upon request; simonteakle.com.

Saks Potts fur-trimmed sweater, $542; matchesfashion.com.

For men

A high-tech weekender will fit elegant staples like well-fitting black denim, a dressed up sweatshirt, and the perfect laced suede boot by shoemaker Carmina. A tweedy overcoat is a gentleman’s staple in London, while tongue-in-cheek glasses by Japanese brand Nackymade add some personality to your gallery-going look.

Prada technical fabric and nylon weekender, $2,220; prada.com.

Ralph Lauren Purple Label jeans, $495; ralphlauren.com.

Tom Ford suede jacket, $8,210; mrporter.com.

Ermenegildo Zegna leather-trimmed cashmere and silk sweater, $995; mrporter.com.

Burberry wool topcoat, $2,995; burberry.com.

Carmina suede boots, $575; carminashoemaker.com.

Nackymade sunglasses, $495; thearmoury.com.

Isaia wool and silk pocket square, $95; isaia.it.

For women

Gone are the days where gallerists and gallery-goers alike are more often than not clad in head-to-toe black. A Marques’ Almeida bag and Max Mara coat in Koons-worthy shades of blue and red come to life with sculptural gold jewelry.

Max Mara camel hair coat, $3,590; matchesfashion.com.

Ji Oh virgin wool culottes, $580; jiohy.com.

Tom Ford cashmere sweater, $1,890; net-a-porter.com.

Robert Clergerie leather slides, $495; netaporter.com.

Marques’Almeida suede bag, $709; farfetch.com.

Tiffany & Co. 18k gold earrings, similar for $5,000; tiffany.com.

Retrovai gold and diamond ring, $2,645; retrouvai.com.

For men

For a far-out adventure, pack lightweight staples that can be easily rolled up or thrown on, like work shirts and chinos. A pair of Alvaro leather sandals or a strand of beads from west-coast LFrank adds a touch of bohéme, and you’re good to go.

Missoni cotton t-shirt, $500; mrporter.com.

Double RL shirt, $185; ralphlauren.com.

Todd Snyder selvedge chino, $198; toddsnyder.com.

Filson leather duffle, $995; filson.com.

Garrett Leight sunglasses, $365; garrettleight.com.

Nick Fouquet embroidered felt hat, $1,100; barneys.com.

Alvaro leather sandals, $400; farfetch.com.

LFrank glass bead necklace, $250; lfrank.com.

For women

Extend summer a little bit longer with richly colored floral prints and creamy silks. A languid slip dress can pair with a linen shirt for day, while a romantic number by Gucci is accented by an ornate wooden clutch for evening. Work with the humidity when it comes to your beauty routine—a salt spray and dash of bright lipstick is all you need.

Gucci crepe dress, $8,200; matchesfashion.com.

Borgo De Noor silk dress, $480; goop.com.

Sies Marjan silk skirt, $690; farfetch.com.

Alumnae pony-hair slide, $650; alumnae.nyc.

Marni x Ruth Van Beek leather tote, $470; farfetch.com.

Silvia Furmanovich 18k gold, diamond, ruby, and wood clutch, price upon request; Bergdorf Goodman; 212-753-7300.

Verdura gold, oval, citrine, and cocobola wood cuff, $37,500; 212-758-3388.

Rahua Enchanted Island Salt Spray, $32; rahua.com.

For men

A grown-up surf look keeps things easy and sleek so you can focus on the art. Brooklyn-based Krammer & Stoudt’s club jacket counts as your initiation, a Ghurka pouch makes itself handy for stray cards or a tablet, and the cult favorite Marine Salve by Make both protects against sun-chapped lips and acts as a light pomade in a pinch.

Krammer & Stoudt khaki jacket, $550; krammer-stoudt.com.

Beams Plus trousers, $160; mrporter.com.

Burberry cotton shirt, $325; mrporter.com.

Sunspel cotton t-shirt, $90; sunspel.com.

Ghurka leather pouch, $595; ghurka.com.

Edward Green suede loafers, $630; leffot.com.

Cartier diver watch, $7,900; cartier.com.

For women

Rose gold baubles by Cartier are all you need to accent a striking, and arty, Rosetta Getty ensemble. Playful trousers from Stella McCartney, a crisp white t-shirt, and the perfect maillot for a late-night dip back at the hotel will round out your week’s wardrobe—and tuck nicely into a sleek Valextra carry-on.

Rosetta Getty knit top, $590, and skirt, $790; net-a-porter.com.

Stella McCartney knit pants, $835; stellamccartney.com.

Max Mara crepe top, $675; net-a-porter.com.

Matteau Swim maillot, $280; matteau-swim.com.

Cartier 18k rose gold, spinel, and diamond earrings, $33,100; cartier.com.

Bottega Veneta intrecciato calfskin sandals, $620; bottegaveneta.com.

Rodin Olio Lusso lipstick, $38; nordstrom.com.

Valextra leather trolley, $8,965; valextra.com.