How to Wear a Travel Backpack Messenger Bag | Round Trip Travel

How to Wear a Travel Backpack

We all know it: that one person in a fanny pack, lanyard, neon tennis shoes, white socks and point-and-shoot camera in hand.  Read: tacky tourist.  Yeah, we’re probably judging them (or actually are one), but we want to be comfortable.  But unfortunately, photos don’t fare well and you feel like a slouchy marshmallow in a groutfit.  At the same time, you still need a way to carry your wallet, camera, passport and handy-dandy granola bar.  No matter your personality, there can be a stylish and functional way for you to wear a travel backpack or bag.Processed with VSCO with p5 preset

Classic Backpack

Pros: This may not be haute couture, but brands like North Face are no junk.  I’m absolutely in love with my bright pink North Face backpack.  This brand offers a variety of styles and gives you more space than your basic purse.  It’s sturdy and known for quality.  Models Cate and Molly both opted for Herschel backpacks which provide space and style.

Cons: Depending on your style, it may go perfectly with your street-style joggers or totally clash with your sundress.  And since it’s on your back, you need to be aware of pickpockets and plan accordingly.

Ideal Trip for this Bag: A classic backpack works well for an outdoorsy trip and for places not overflowing with pickpockets (like big, bustling cities).  If space and comfort are your top priorities, this is the way to

Drawstring Bag

Pros: Assuming you’re not opting for plastic, a drawstring bag offers a more sophisticated and stylish option than your run-of-the-mill backpack.  Plus, you don’t have to worry about a pickpocket sneakily unzipping your bag to snatch a wallet.  Cate modeled a black leather bag from Victoria’s Secret.

Cons: It’s on your back which means out of sight and potentially less security.  There’s also less support for your shoulders.

Ideal Trip for this Bag: If you’re planning on taking some sweet model shots for your next Insta and don’t need to carry too much, a drawstring bag may be just perfect for


Pros: You can get much more creative with appearance: leather, quilted, zipper, snap, pockets.  Even better, it’s at your side, meaning you can easily access it and make sure others can’t do the same.  Cate modeled a gray crossbody purchased in London.

Cons: There’s most likely less space than other options, and it can strain your shoulder.

Ideal Trip for this Bag: Crossbody bags are fantastic for city trips.  If safety and accessibility are most important to you, this type of bag will do just those things for

Shoulder Bag

Pros: A shoulder bag can provide a decent amount of space as well as allow you many options for color and design.  You can rest easier knowing someone would have to go through your arm pit to unzip a shoulder bag with a short strap.  Molly modeled a brown leather tote from J. Jill.

Cons: One shoulder might get a big overworked, and this type of bag requires a bit more commitment than a cross body bag (which is fully hands-free).  If you opt for a shoulder bag with a longer strap (your classic shoulder purse), be aware of snatchers.

Ideal Trip for this Bag: Shoulder bags are also ideal for pickpocket hotspots but don’t offer the hands-free nature of a crossbody.  However, I’m opting for a shoulder bag for my summer in France as it offers space and

The Verdicts

Cate: “My favorite travel bag is my large, brown leather tote from J.Jill.  Just big enough to fit in an extra cardigan but still flexible enough to be shoved in small places whether I’m in the car, train or plane.  It is simple yet turns any outfit chic!”

Molly: “My favorite bag for traveling would probably have to be my backpack.  I love the fact that it’s out of the way, and it fits everything I need.”

Kristin: “On my trip to Europe several summers ago, I opted for a Vera Bradley crossbody bag.  I felt very secure as I could easily hold the bag close to me in crowded areas.  I squeezed my Nikon, passport, wallet and brochures all into my Hipster which was entirely convenient but also strained my shoulder.  With a summer in Europe approaching, I bought a BCBG shoulder/handbag, and I’m hooked.  I feel so regal, feminine and powerful with this spacious and practical bag on my arm.”how-to-wear-a-travel-backpack-columbia-mo-round-trip-travel

On the Models

Cate: Sweater (Loft), leggings (Loft), socks (J. Crew), booties (Anthropologie).

Molly: Sweater (American Eagle), leggings (T.J.Maxx), shoes (thrifted).

Travel can be difficult, but choosing the right bag can make your trip that much smoother. Happy shopping!

13 thoughts on “How to Wear a Travel Backpack

    • roundtriptravel says:

      Thanks for stopping by, Amy! You can never go wrong with a classic. I love your blog! Just read your post on traveling solo vs traveling with friends. I’ve read so many on traveling solo, and I like that you compared both. Happy traveling!


  1. Alpine Bear says:

    Yeah Nice styling beautiful to see 🙂 ! According to my point of view if somebody want to carry the basic luggage in his/her backpack then those kinds of backpacks don’t have enough size so i would like to recommend a ” Black-light backpack” in
    such case as this backpack made all nylon less in weight,durable and water resistant as compared to polyester .This backpack can be used anywhere like office,school,college ,trip,hiking and other adventurer days as well as it is affordable to buy.

    Liked by 1 person

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