I Took Oprah’s Genius Bag Style on 3 Trips—This Millennial-Coded Staple Is the One Item Your Suitcase Is Missing

People watch at any West Village or SoHo street corner, and you’ll find all kinds of folks spilling out of restaurants and bars. But if they’re under the age of 29, I can guarantee they’ve tucked a tiny shoulder bag under their arm. At some point, my generation decided crossbody bags were old news, but ditching this functional accessory is a mistake. In fact, lightweight crossbody bags are my go-to travel essentials—they keep belongings strapped close and let you go hands-free without worrying about your purse slipping off your shoulder. 

Plus, high-fashion and luxe brands certainly haven’t bidden adieu to the millennial-coded style. While everyone focused on Sarah Jessica Parker’s cartoonishly large hat last year, I spotted her Pierre Cardin messenger bag; not to mention a number of very chicParis Fashion Week guests styling Chanel bags and printed purses across their bodies earlier this month. So, sure, shoulder bags and large totes have their time and place, but while traveling, I am loyal to the crossbody bag, especially with so many stylish options. 

Ahead, shop the lightweight crossbody bags I brought with me on three different vacations and more practical picks, including Oprah’s favorite style, a Martha Stewart-worn brand, and Jodie Foster lookalikes. 

3 Lightweight Crossbody Bags for Travel

• Hailey Bieber-Worn Brand: JW Pei FEI Faux Bamboo Woven Phone Bag, $99; jwpei.com
• Save for a Rainy Day:Baggu Small Nylon Crescent Bag, $52; amazon.com
• A Splurge You Won’t Regret:Maison de Sabre Mini Leather Flap Bag, $339; nordstrom.com

JW Pei Fei Faux Bamboo Woven Phone Bag

$99 at Jwpei.com

It’s hard to keep track of the celebrities who’ve carried JW Pei’s novelty bags, including Gigi Hadid, Hailey Bieber, Selena Gomez, and Anne Hathaway. It makes sense, considering its vast collection has a style to suit everyone’s aesthetics and needs, from the quirky to the understated. I was thrilled to discover its woven phone bag was large enough to carry my phone, hotel key, and lip gloss. Meanwhile, its rattan texture added a very cute, beachy twist to all my outfits, perfect for my L.A. trip.       

Maison de Sabre Mini Leather Flap Bag

$339 at Nordstrom

I’ve learned that it always pays off to spend more on these two closet staples: shoes and purses. The timeless Maison de Sabre flap bag is a worthy splurge, especially given its classic shape and fine craftsmanship that will withstand any trend. Additionally, it's very lightweight—I was actually thankful for the crossbody feature because I kept fearing I left it behind. Despite the featherweight feel, its handcrafted leather is extremely durable and sturdy. I’m also fond of the compact rectangle shape—although it's small, the bag is deep, allowing me to fit way more than I thought possible. 

Baggu Small Nylon Crescent Bag

$52 at Amazon

Everyone knows cool girls wear Baggu (hi, Katie Holmes, SJP, and Olivia Wilde), with the 

The Baggu crescent bag being its most popular style. The nylon bag is easily the lightest travel bag I own, especially since its unique shape helps distribute your belongings evenly inside. Plus, the material is truly water-resistant—I took it on several river raft rides at Disney World and got drenched during a spontaneous Florida rainstorm, and all my items remained nice and dry. 

Ahead, shop more crossbody styles, like Oprah’s favorite pick, and my most-complimented style from a Martha Stewart-worn brand.  

Mali+Lili Gail Vegan Leather Multi-Compartment Crossbody Bag

$78

$38 at Amazon

Uniqlo Round Mini Shoulder Bag

$25

$20 at Uniqlo.com

Bandolier Taylor Bag

$268 at Bandolierstyle.com

Bagsmart Crossbody Hobo Bag

$28

$18 at Amazon