Destination Chic: Travel Outfits for Montage & Pendry

From resort wear in Los Cabos to coastal style in San Diego and sophisticated city looks in Chicago, discover travel outfit inspiration for every destination.

By Paula Lee

Resort Wear for Los Cabos

Montage Los Cabos

A getaway south of the border calls for resort-ready pieces in a dreamy sun-washed palette punctuated by artisanal notes. For pool days at Montage Los Cabos, hit the pool in a standout swimsuit, such as Celine’s monogram halter one-piece ($1,050, celine.com) and top it off with Gigi Burris Millinery’s packable raffia sun hat ($440, gigiburris.com). For alfresco dinner plans, Ancient Greek Sandals’ beaded thongs ($220, ancient-greek-sandals.com) make for an effortless pairing with any outfit. Infuse a touch of whimsy by way of a Chloé woven leather bag with a toucan handle ($3,800, chloe.com). And because there’s nothing more glamorous than golden jewelry against sun-kissed skin, look to opulent adornments like Jenna Blake’s diamond-framed seashell pendant necklace ($25,600, jennablake.com) and CCWW’s drop earrings (price upon request, ccwwdesigns.com) for a statement that lingers beyond the beach.

Beach at Montage Los Cabso
Celine bathing suit
Chloe purse
Ancient Greek Sandals
Pendry San Diego pool
Prada leather tote
Orlebar Brown shirt
Brunello Cucinelli shoes
Loewe shorts

Style Guide for San Diego

Pendry San Diego

There’s something about the SoCal coast that feels inherently nostalgic—and these easygoing yet elevated separates embrace that laid-back spirit. For a stay at Pendry San Diego, build your vacation look around Orlebar Brown’s embroidered jacquard cotton camp shirt ($595, orlebarbrown.com) and Loewe’s drawstring shorts ($1,100, loewe.com). San Diego is a flip-flops and sneakers kind of town: Fit in and stay stylish with Brunello Cucinelli’s velvety reversed calfskin lace-ups ($1,350, brunellocucinelli.com). Cool sunglasses are also a must around here, and Garrett Leight’s acetate aviators ($495, garrettleight.com) quietly channel a retro sensibility. Pair them with Prada’s durable canvas and leather-trimmed tote ($3,500, prada.com)—it’s big enough for all the travel essentials. And if a touch of color is in order, go for one of Luis Morais’s beaded gemstone bracelets ($680 each, luismorais.com).

Travel Outfits for Chicago

Pendry Chicago

Whether a quick business trip or leisurely stay at Pendry Chicago, consider leaning into the city’s storied Art Deco architecture for a sartorial splash of inspiration.

For Her: Statement Accessories

For her, it’s all about accessories. Take in The Loop in Hermès’s flat wrap sandals ($1,525, hermes.com), Jade Ruzzo’s 18K gold and diamond earrings ($5,600, jaderuzzo.com), and Stephen Silver’s exquisite emerald and diamond pendant on cord necklace (price upon request, shsilver.com), while a pair of Bottega Veneta sunglasses ($760, bottegaveneta.com) showcases the brand’s signature metal knot.

For Him: Refined Texture

When it comes to men, the Art Deco look demands a casual yet refined style with rich texture. Canali’s jacquard-knit houndstooth polo ($950, canali.com) pairs beautifully with Loro Piana’s woven linen trousers ($1,110, loropiana.com). And for a touch of flair that wows, strap on Jaeger-LeCoultre’s new limited-edition Reverso Tribute watch (price upon request, jaeger-lecoultre.com): Flip the handsome dial to reveal the intricate Japanese enamelwork on the caseback, echoing the ornate decorative style of the 1920s.

Pendry Chicago
Hermes flats
Jade Ruzzo earrings
Bottega sunglasses
Stephen Silver necklace
Canali polo
Jaeger LeCoultre watch
Loro Piana pants