The best convertible backpack overall
The infinitely photogenic Senreve Maestra is that rare unicorn — a bag that is extremely cool and extremely practical at the same time. Made of gorgeous scratch- and water-resistant Italian leather, it has a truly unique design and multiple special features that make it worth the splurge.
And a splurge it is, with the largest size costing nearly $1,000. You can choose to pay the entire cost up front or in interest-free installments. But if you’re looking to invest in a bag you’ll use daily, this is a great option. The straps can be adjusted to turn the Maestra into a backpack, satchel, crossbody, or tote.
Each size has multiple interior pockets including a padded compartment for devices. The largest fits up to a 15-inch laptop and the smallest can hold an iPad Mini.
Insider Picks editor Sally Kaplan loves her full-size Maestra, calling it, “a luxury, but it's one that you will get tons of use out of.” The bag has also been featured by Purseblog and Travel + Leisure.
Pros: Can be worn four ways, comes in three sizes, 100% Italian leather, multiple interior pockets
Cons: Expensive
Buy the standard Maestra for $895-$995 Buy the Midi Maestra for $795-$875 Buy the Mini Maestra for $695-$775The best convertible backpack for travel
If you’re constantly on-the-go you need a bag that moves with you, and the Timbuk2 Jet Set Convertible Travel Backpack is that bag. It’s attractive, with a slouchy silhouette and cool buckle details. Plus, it's super practical for a busy lifestyle.
The Jet Set Convertible Travel Backpack was designed in conjunction with Phoebe Dahl (yes, she’s author Roald’s granddaughter). It has backpack straps so you can wear it on your shoulders and a top strap that allows you to carry it more like a satchel.
According to the product description it can be worn eight ways total, including as a tote or shoulder bag. There’s also a detachable pouch that can be worn on its own or as a front pocket.
This bag is carry-on friendly and features a removable passport pocket that attaches to the crossbody handle. It comes in blue, black, and a currently sold-out metallic shade that I really hope comes back in stock because it’s super cute. Reviewers on the Timbuk2 website love the look of the bag and flexibility, but some say it doesn’t fit a ton inside, so keep that in mind.
Timbuk2’s convertible backpack has been featured by Yahoo and The Zoe Report. Insider Picks' guides editor Malarie Gokey has also tried it out and loves it. She appreciates the high-quality leather and the way it effortlessly transitions to be any kind of bag she needs during the day.
Pros: Can be worn eight ways, detachable front pouch and interior passport pocket, carry-on friendly
Cons: Doesn’t fit a ton of stuff
Buy the Jet Set Convertible Travel Backpack for $299The best water-resistant convertible backpack
My purse always seems to get wet when it rains, whether I’ve got an umbrella or not. It doesn’t even seem to matter how wide the umbrella is, either — droplets always trickle down and hit the outside of my bag. The Samsonite Encompass Convertible Tote Backpack has a water resistant coating to protect your precious cargo.
This bag can be worn five different ways — backpack, shoulder bag, crossbody, tote, and hand-held satchel. The special features make it a dream come true for organization obsessives. They include a water bottle sleeve, key FOB, luggage loop, padded tablet and laptop pockets, an RFID data “vault” to protect you from identity theft, and a front pocket with pen sleeves.
And if you get caught in a rainstorm, you can trust it all to stay safe thanks to the protective exterior. The bag isn’t made of leather but it still looks really sleek and comes in three versatile colors: black, bordeaux, and stone.
Insider Picks' guides editor Malarie Gokey uses this bag almost every day for work. She loves how easily in transitions between a backpack and a tote bag, so she can stuff her laptop inside and pack it full to the brim without wearing it as a tote bag and killing her shoulders. It has also survived a snow storm and a spilled cup of water without getting wet inside at all.
Pros: Water-resistant, convertible in five ways, tons of pockets for electronics and small items
Cons: Not fully waterproof, not leather
Buy the Encompass Convertible Tote Backpack for $240The best convertible backpack under $100
If you don’t have the funds or the inclination to majorly splurge on a convertible bag, the Carhartt Legacy Hybrid is a great option. It has a bit more of a rugged, outdoorsy look to it, but would still look at home in any startup’s open plan office.
And if you are the outdoorsy type, you’ll be pleased to know this bag can withstand some serious wear-and-tear. It’s made of 100% polyester and is treated with Rain Defender water repellent. As with the other picks this list, you can wear it as a backpack or a tote bag.
Inside, there’s a large zippered compartment with a padded laptop sleeve and two smaller pockets. On the outside is a zippered pocket and two other slash pockets. We’ve previously featured the Carhartt Legacy Hybrid as a favorite convertible bag option.
It’s not huge so I wouldn’t recommend relying on it to pack for a long trip, but it’s perfect for a day journey or for your hour-plus commute.
Pros: Durable, water-resistant, laptop sleeve and three interior pockets
Cons: Small, fewer ways to adjust straps
Buy the Carhartt Legacy Hybrid Convertible Backpack Tote Bag for $54.99 to $62.99The best convertible backpack for long weekends
“You’re not any one thing, why should your bag be?” That’s how the product description for the Caraa Studio Bag begins, and let me tell you — this bag is way more than just one thing. It’s your overnight duffle for a long weekend, chic backpack for work, the gym bag you’ll always get compliments on.
As Travel + Leisure puts it, “a duffel, backpack, and cross-body all in one.” Like the aforementioned Senreve Maestra, it’s very striking to look at, but also incredibly useful. It looks equally cute worn on your back and carried by the top-handles. There are three sizes — Studio Bag, Studio Bag Medium, and Studio Bag Large — to suit your lifestyle needs.
The array of cool features, including moisture-wicking backpack straps and antimicrobial, waterproof lining, make this bag unique compared to its counterparts. I especially love the idea of the waterproof pouches for shoes and clothing.
Refinery 29, Self, Observer, and Fast Company have all recommended the Caraa Studio Bag.
Pros: Can be worn as duffle, backpack, crossbody, or tote, waterproof and antimicrobial lining, tons of pockets and features
Cons: Expensive
Buy the Studio Bag for $395 Buy the Studio Bag Medium for $425 Buy the Studio Bag Large for $450
