Travel Better With These Personal Item Bags and Accessories

Before we dive into the gear, let’s address a common misconception. While there are bags designed to max out every cubic inch of the personal item allowance, that’s not my focus here. Instead, I’m championing a minimalist approach – one that values quality, functionality, and aesthetics over sheer capacity. As someone who once traversed Italy for 30 days with nothing more than a 19-liter backpack, I can attest to the liberating power of traveling light.

This selection prioritizes superior functionality, pleasing aesthetics, and durability. If you’re seeking the absolute largest bag to cram in the maximum amount of stuff, this guide may not be for you. But if you’re after quality gear that looks great, functions flawlessly, and stands the test of time, you’re in the right place.

These bags offer easy access to the guts while rushing from landing to departure gates so you can eat a snack or pack your hoody, without missing your connecting flight.

The Ancoats Bag Company’s Diplomat

The Diplomat from Ancoats Bag Company is a masterclass in custom craftsmanship. The Diplomat is custom-made from your choice of fabrics and available in 3 sizes: 16″: 37 x 27 x 5cm, 14″: 34 x 25 x 5cm, 13″: 32 x 23.5 x 5cm and includes a built-in padded laptop compartment. For a briefcase style daily driver, I’ve never come across a bag more well-made. The attention to detail and thoughtful design makes this a sight to behold for bag lovers. It features two half slip pockets on the front and a larger Velcro slip pocket on the back that has a Velcro-close rear pass-through panel, which can double as a small magazine stash, but also allows the Diplomat to piggy-back the Ancoats Tote. Inside you’ll find the padded slip for your laptop along with slip pockets for pens, a phone, chargers, etc.

I have the 14″. It’s tiny. Tiny enough that people might think you’re crazy for traveling with just this bag. But if I’m just going for a night or two this can hold all the items I mentioned plus a couple of pairs of socks, undies, a spare Tee, a pair of shorts, and my toiletries. Everything I need along with leaving me plenty of legroom when I stow it under the seat in front of me. If you want to go as minimal as possible without sacrificing usability and luxury craftsmanship, take a closer look at the Diplomat.

Rickshaw Messenger

My love for Rickshaw bags is no secret. Their bags leverage simple, functional design with top-quality craftsmanship and dip it all in a giant bowl of custom sauce. Yep, they make their bags to order and let you pick the fabric combinations, no matter how weird. They won’t stop you. Exhibit A: my medium Zero Messenger in Lazer Yellow exterior with Pink lining and Spa Blue Binding. Sometimes you want a bag that doesn’t draw attention to itself. Other times… well… this. Looking at it giving you a headache? I totally get it. But I love it! Lucky for you it’s available in hundreds of color combinations. Whatever combo you go with, the medium messenger features two large outside slip pockets along with Velcro on the inside for optional accessory pockets like the Laptop Insert and handy Deluxe Pocket which adds a zippered compartment along with slip pockets for pens, etc. Sized at 6″ x 12.5″ x 10.5″ the nearly 13-liter Medium Zero falls well below the max allowed for a personal item bag, yet still expertly holds everything I could need for a 3-5 day trip.

The Large Zero Messenger has all the same features, but ups the size to 8.5″ x 13″ x 12” – still small enough to qualify as a personal item, but holding nearly a whopping 22 liters! I can (and have) traveled the world for weeks on end and still have room left over. The customizability and simplicity of this design along with its great looks makes the Large Zero my most used travel bag (and I have a LOT of bags). My favorite feature of both bags is, when packed correctly, they will stand up on their own in between your feet under the seat in front of you. No need to join the straps up or straps down debate.

If you’ve never thought about traveling with the time-tested duffel, it’s time to start thinking about it. If you want to stuff the maximum amount in the smallest space, duffels may become your new best friend. They are an easy-access storage bucket that quickly slides back from under the seat in front of you.

Mission Workshop’s Helmsman VX

The phrase “High-End Duffel Bag” may sound like an oxymoron, but leave it to Mission Workshop to deliver with their weatherproof Helmsman VX. At 17″ x 11.5″ x 8.5″ (27.2 liters) it just squeaks in under the max dimensions for a personal item on most US flights. It includes one massive zip pocket on the inside and 2 zip outside pockets on the ends, along with four easy-access slip pockets. Hideaway grab handles and a smooth shoulder strap are included, but if you want to backpack carry this expertly crafted container, you can add the optional backpack straps. This massive bag weighs only 2 lbs. If duffel carry is your jam, and you want one of the most usable, best-made, nicest-looking duffels on the market, make the Helmsman VX your first stop.

Rickshaw Getaway – Money Edition

The Rickshaw Getaway – Money Edition is a fun and visually striking take on the already awesome Rickshaw Getaway Duffel. The Getaway looks small, but the 9″ x 9″ x 18″ bag will hold 24 liters inside. The bag weighs just 1.6 lbs and features one external zip pocket along with two slip and two zip internal pockets. They even put in a padded bottom – a great touch! Webbing handles for quick grab are included, as well as a quick-adjust shoulder strap for crossbody and shoulder carry. What the Money Edition adds to the already excellent Getaway is a custom printed “$100 Bills” lining and a big splashproof #8 AquaGuard zipper. Add a couple of your own packing cubes (Peak Design makes my favorites) to keep the large open inside organized and you’ll be zipping from country to country for weeks on end in style!

If you’re landing in Heathrow, make sure you’re wearing your best walking shoes and your bag is a backpack. You’ll be hitting your 10,000 steps just getting from your gate to the Tube. Though backpacks aren’t my most used style of bag, they will maximize your carrying comfort but at the expense of access. If you’re wearing it more than retrieving things from it, strap one of these puppies on.

DEFY Bucktown X-Pac Edition

The DEFY Bucktown X-Pac Edition is a 2.2 lb. 23-liter backpack, 12″ x 19″ x 6″ with top-quality materials and construction. The shoulder straps are incredibly comfortable with the perfect amount of padding. The top grab handle makes it a breeze to extract from under the seat in front of you. The built-in organization is just right too, with a padded laptop compartment that’ll hold up to a 16-incher. Nice. The same area also has plenty of room for packing cubes filled with your favorite travel clothes. Moving forward, another splashproof zip slides open to reveal what I’d call the “work” area. The perfect place to keep things you might use on a flight, books, pens, snacks, sunglasses. This area had a couple of slots for pens, a phone, and a heavy-duty metal key clip that looks so nice.

The outside features two water bottle pockets, but they aren’t super deep, so I wouldn’t put any bottles over 22 ounces in those for fear they’d fall out when I took the bag off. There’s one more splashproof zip pocket on the very front of the bag, the perfect place for chargers, cables, and the like. There’s even a Velcro patch for your customizing pleasure. Personally, I keep the included DEFY patch on there as I think it looks striking. Altogether this bag is a looker with top-notch construction and materials adding up to an incredibly usable bag that’s built to last.

Tom Bihn Synik 22

The Tom Bihn Synik 22 is a fun reimaging of the TB Synapse. The Synapse is one of the most useful designs in the history of backpacks, but only comes in a 19 or 25-liter version. The Synik bridges the gap and also marries the more daily carry design of the Synapse with a suitcase-style full clamshell zipper opening on the main compartment that features removable tiedown straps to keep your clothes from falling all over the place.

The 22-liter bag is 11.4″ x 16.0″ x 9″ but seems to hold more yet look smaller. Impressive. There’s a padded top handle and a padded bottom compartment along with a padded back panel and shoulder straps that are padded to the point of overkill. There’s a side access zip for your 13″ laptop, but the compartment is only padded on the back side. This is fine if you are packing clothes on the inside, but I wouldn’t put anything hard or sharp on the inside if you’re carrying your laptop loose in the side compartment. They’ve kept the 5 external zip pockets from the Synapse. Having all these pockets accessible from the outside makes it one of the most usable travel bags to live out of. Anything you could need is just a quick zip away. They’ve also kept the expert construction and attention to detail. Anyone looking for the perfect mix of suitcase and daily driver with excellent usability for your world travels, don’t miss the Synik 22 by Tom Bihn.

Black Ember Forge Max

The Black Ember Forge Max in Multicam Black is an 18″ x 12″ x 6″ masterpiece that transforms on the go. It expands from 20-30 liters with a simple slide of the zipper. It also has an extremely comfortable padded back panel that quickly hides away the perfectly padded shoulder straps when using the bag in briefcase mode with the included (removable) briefcase handles. It also includes a removable padded shoulder strap and removable Maglock compression straps.

It’s been smartly designed with a multitude of slip and zip pockets throughout including an integrated laptop compartment that easily holds up to a 15″ computer, and a dedicated middle section for clothes. Combine that with the top-quality craftsmanship (right up there with the best I’ve ever seen), AquaGuard zippers, and rugged fabric, and this could be the perfect digital nomad bag for your world travels. At 3.5 lbs. it’s not the lightest bag out there but it’s definitely one of the most versatile and best-designed bags I’ve seen in years.

It’s also one of those bags that I can’t leave the house without a stranger mentioning how nice it looks. And they’re right. It’s a looker. If you don’t like talking to strangers and you need the smallest, lightest bag for your travels, you can pass on the Forge Max. But if you want a top-quality bag that has clearly been designed to live and work out of and look great doing it, that’s built to last, and gives you the flexibility to transform it on the go, check out the impressive Forge Max from Black Ember.

When I one-bag-travel, I ALWAYS have more than one bag. In my daily use I can easily get away with just one bag or sometimes – dare I say it – no bags at all! But when I travel I always have one main bag and then extra bags either inside that bag, or strapped to my body. What am I talking about? I’ll show you.

Hip packs! I’ve never once been told by an airline or security that I couldn’t have one of these compact hip packs in addition to my personal item bag – though you may end up with a different experience, so proceed at your own risk. Please note, I said “compact” hip packs. If it’s not small, I do think you’re pressing your luck. Having a hip pack for most of the things I’ll need during the flight lets me leave my main bag where it is. It also works as a small about-town bag at my destination.

Thrupack Ultra Summit Bum with Comfy Strap

If you want something super comfortable, but without any bells and whistles, go with the Thrupack Ultra Summit Bum with Comfy Strap. They use Challenge Ultra 200 fabric that is extremely strong for its ultra-low weight, making this 9″x5″x3″ 2.5-liter pack weigh in at just 2.4 oz without the strap – and 4.9 oz with the Comfy Strap. But the strap is not attached to the bag, so you can slide it onto your belt or a strap on your main bag as long as it’s less than 2″ wide. Very handy.

The back side of the Summit Bum features a breathable padded mesh, so feel free to get a workout in, the bag won’t get you extra sweaty. There’s also an open slip pocket for frequently accessed items like a phone or sunglasses. Bonus, they’ve put a small loop on each side of the back so you can use your own clips to attach it to another bag or to the outside pocket of the seat back in front of you. Behind the single AquaGuard zipper in the main compartment you’ll find two small slip pockets, each half the length of the bag. Personally, I would have preferred just one long one that could hold a phone, but it’s good for keeping keys and earbuds separated. The rest of the compartment is wide open for your snacks, charger, cable, backup batteries, etc. I think you could even get a small windbreaker in there if you rolled it up. A rugged, ultralight, simple hip pack with flexible carry options and a breathable back panel? Yes, please! Check out the Thrupack Ultra Summit Bum with Comfy Strap.

Patagonia Ultralight Black Hole Mini

The most compact, but still usable hip pack I’ve found is the excellent Patagonia Ultralight Black Hole Mini. This 1-liter hip pack features a breathable mesh back panel along with two zip pockets. It easily holds my phone, bag of trail mix, hanky, keys, pen, small notebook, backup phone battery, flashlight, lip balm, sunscreen stick, and earbuds with room to spare.

It’s small enough to squeeze into all but the most overstuffed bags when going through security, but big enough to hold everything I need quick access to on a long flight except a water bottle. At 3.5 oz. it weighs almost nothing, but its usefulness makes it one of my most frequently used bags for long walks and short flights.

North St. Bags Pioneer 12

My overall favorite hip pack for travel is the North St. Bags Pioneer 12. This makes a great organizer bag for inside your larger bag and is big enough for me to be a daily travel carry for most vacation situations. If I’m taking a warm weather weekend trip and don’t need to bring my laptop, the 5.7-liter Pioneer 12 (12″ x 7.5″ x 4″) is big enough to be my only bag with room for all my in-flight essentials and enough left over for extra shorts, socks, undies, and toiletries. If I’m using it as my sneaky extra bag it’s big enough to hold everything I’d need for even a transcontinental flight including lots of snacks and even a water bottle. It’s also designed for flex use. The removable waist strap is plenty long enough to use cross-body. There’s an optional handlebar kit if that’s how you roll. And there are multiple attachment points if you’d like to hang it to the seatback pocket in front of you or attach it to the outside of your main bag.

There are multiple organization slip pockets along with an external zip pocket and an internal zip pocket, but it also features a Velcro strip on the inside to add an optional additional zip pouch like the Shortstack Pouch. Like all the gear I’ve tried from North St. Bags, the quality of materials and made-in-the-USA construction is top-notch. If you’re looking for a versatile compact carry with plenty of built-in organization that’s built to last for a day bag or inflight essentials bag, don’t miss the Pioneer 12 from North St. Bags.

Bonus: North St. Bags also makes one of my favorite totes, the upcycled 26L Tabor Tote. Did you know most airlines let you bring a bag of food onto the plane that doesn’t count towards your bag limit? I found a small, simple tote works great for this.

Pouches:

I’m not a “route around in the bottom of my bag for stuff” kind of guy. I like to over-organize my bags – you could call it a hobby of mine. That’s why I LOVE pouches. The kind of pouches you’ll want should be very specific to how you carry. For me, these Rickshaw Bagworks pouches are my favorites.

Simple Pocket – For adding a secure zip pocket to any bag with its Velcro strip.

Zipper Pouch Mini – A flat 6×4″ pouch to toss in your bag.

Plush Micro Pouch – A tiny 4.25 x 1.25 x 0.75″ for organizing super-small items.

SweetPea Mini-Lanyard Pouch – A handy pouch for tiny things. I keep my earbuds in here and attach it to the inside of my bags with a clip so I can always find it quickly.

Hero Pouch – 4″ x 5.75″ with a 3″ bottom makes for a 3D pouch that’s great for USB cables, backup batteries, etc., or even a mini toiletry bag.

I’ve always believed that the less you carry, the better quality your carry items need to be. So when I travel what makes the cut?

Travel Keyboard – If I’m just away for a weekend of fun, I’m not bringing a laptop, but if I’m taking a work trip that requires a lot of typing I’m not only bringing my laptop, but also a compact mechanical BT keyboard. Not only do I type faster on a mechanical keyboard, but the experience is SO much nicer. It’s so nice, that if I’m traveling for work and don’t need to do any video editing, I’ll just bring my phone along with this BT keyboard and happily write sometimes for hours. It’s the Keychron K7 Pro. This wireless/wired keyboard has a 65% layout so it’s super small and features ultra-slim keys that somehow still feel like full keystrokes. I originally got this so I could duplicate the pleasure of typing on the mechanical keyboard I used at home while traveling, but I liked it so much more than my home keyboard, I now use this one at home AND on the road. I went with the red key switches that give just the right amount of audible click without being distracting.

At just 22mm thick, it’s shorter than a quarter. And it’s only 12.04″ x 3.83″ so it easily slips into just about any bag – even my beloved North St. hip pack. It weighs just under 1 lb. but that includes the built-in 1550 mAh rechargeable li-po battery that’ll keep it clicking away for 130 hours over a BT connection. It feels like the perfect weight to me as it doesn’t move around when I’m typing. The built-in legs let you adjust it to 3 different angles, though I keep it flat. At first, I thought the space-saving omission of the F Keys row might be a deal breaker for everyday use – but a sacrifice I could make for travel, but I’ve been using this keyboard exclusively at home for all my projects including video editing and thanks to the customizable key combos, I find I actually work faster with this setup than on a non-customizable 100% keyboard. It doesn’t happen often, but I love when I get something compact for travel that ends up being so well-made that I use it every day. And that’s what happened with the impressive Keychron K7 Pro.

ANC Headphones – For me these are an absolute must for any airline travel. It’s the difference between me arriving feeling human or stumbling off the plane a complete zombie from all the buzz, hum, and rattle assaulting my brain for hours on end. I love the compact size of earbuds over headphones, but you have to find a comfortable pair with a battery that can last the whole flight. I’ve been using the EarFun Air Pro 3 which can be grabbed on sale sometimes for as low as $55. But don’t let the low price fool you. These sound great. And they can lower that annoying inflight rattle by up to 43dB. The cherry on the sundae is that these almost weightless little marvels will pump out the tunes for up to 9 hours without a recharge and with enough extra juice in the included case to extend those 9-hour sessions to 45! And they’re so inexpensive, if I had a flight much over 9 hours, I’d buy a backup pair and swap them for a nonstop flight of silence. Only, I don’t have to get a backup pair because they just launched the EarFun Air Pro 4 and they are even better!

If you time it right with a sale, the 4 can be had for just over $70. If money is super tight, go with the 3’s – you won’t be disappointed, but if you can spring for the extra cash, the EarFun Air Pro 4 are stuffed with the latest ANC (up to a 50dB reduction) and BT tech and will run for a whopping 11 hours without throwing them back in the case for a 10-minute quick charge to get an extra 2 hours or full charge multiple times for up to a total of 52 hours before needing to charge the case again. Though the 3 is comfortable and stays in the ear for all but the most rigorous activities, the 4 are the most comfortable earbuds I’ve worn and haven’t fallen out once.

Power – Did you know, a long, long time ago, people traveled the world without electronics! It’s true. Don’t be scared. Now that we all have phones, wireless earbuds, smart watches, and tablets a long trip requires power. And if you’re going the minimalist route, you’ll want top quality in a compact package. That’s why these days I’m not leaving for a trip without the small but mighty Anker Nano 3 30w Charger. It’s only 1.12″ × 1.12″ × 1.39″ – basically the size of an ice cube – yet it spits out 30w of fast charging and is dual voltage for world travel. It has built-in safe charging features and can be picked up for as low as $15.

If you need more power or the ability to charge multiple devices at the same time, step it up to the Prime Anker 100W GaN Wall Charger. It’s a little more than double the size but offers tons of juice and charging for two USB C and one USB A device all at the same time. And if I can’t be tied to a wall plug, I’ve always got the Anker Nano Power Bank. It packs a 10,000mAh battery into a 4.09″ × 2.06″ × 1.02″ cube that has two-way 30w fast charging.

Tools – I like to keep the excellent Leatherman Signal multitool handy on my daily adventures and often have the Micra on me if I’m just doing pocket carry for the day. But neither of these can come along if you’re hitting the friendly skies. So what’s a tool-loving traveler to do? Carry a tiny screwdriver!

I’m a huge fan of the 711L Lollipop Bit Driver. It’s just over 3.5″ long including the bit, but swing out the nested shaft at 90 degrees and you can get a crazy amount of torque. Or keep the shaft nested and drive in your screw single-handed by pressing your palm against the end. It’s the nicest screwdriver I’ve ever used. Also, it looks really cool!

Want to add a ratcheting feature and go as ultra-compact itty bitty as possible? 711L also makes the surprisingly useful Mini Ratchet Wrench. It’s just 2″ long yet made strong enough for auto repair. Combine this with a compact bit extender and a couple of different bits like the Leatherman Bit Driver Kit and you’ve got one of the world’s smallest toolkits.

Water Bottles – I’ve got way too many water bottles. They are big and round and don’t use the space in my bag efficiently. Enter memobottle. I’ve got the SLIM Stainless Steel memobottle (Black) and the A6 Stainless Steel memobottle (White). Both bottles look like something you’d find in a design museum. They are a little weird to hold, but are smooth and nice on the lips. Most importantly, the non-tube design means they slip into small spaces in my bag without hogging up real estate. They aren’t insulated, but that allows them to hold more water in less space with the SLIM holding 20oz in its 10.6″ x 2.3″ x 1.5″ cuboid shape and the A6 holding 16oz in its 10.6″ x 2.3″ x 1.5″ dimensions. For my daily driver, I’m going to stick with my insulated tube-shaped Hydro Flasks, but for ultra-compact air travel, memobottle is my pick.

Nail Cutter – If I’m going to be away for much more than a week, I’ve got to bring a nail cutter with me. Sure, I can just buy a cheap one at a drug store, but then it’s all sharp and a mess. I find it very distracting and always end up having to file them. Well, not anymore. I recently got hold of the excellent EDJY Nail Cutter. They go into great detail on their website about why these are superior nail care implements – I found it quite interesting. But to give you the TLDR, unlike traditional nail clippers that use two sharp edges clapping together to essentially chew your fingernail off and fly it across the room, the EDJY Nail Cutter uses only one sharp side to slice the nail away, leaving it smooth and tidy and without the need to file off any ragged ends. It also catches the clippings. It’s not the smallest clipper by any means, but it weighs almost nothing and provides the nicest results I’ve seen in a nail trimmer.

Flip Flops – I can’t remember the last time I traveled without a pair of flip flops. Recently I upgraded my flipflop game with the Circadian Sandals from Earth Runners. These weigh just 5.9 oz and are only 9mm thick. These are minimalist footwear designed to give you the barefoot experience. The footbed is held to your foot with a single length of webbing with conductive stainless steel thread (more on that in a second) and a US-made buckle for adjusting the fit on the fly. Wearing these is the closest you can get to walking around barefoot without actually being barefoot. Not only is the footbed flat and wide, they use a copper plug that passes through the sandals to the ground below. It’s connected to the conductive webbing grounding your body to the earth.

I’m not going to get into the benefits of barefoot shoes and sandals, but I will say except for rare occasions requiring fancy shoes, it’s the only kind of footwear I use. I’m also not going to dive deep into the benefits of Earthing or grounding yourself to the Earth, but you may want to look into it. Top level athletes are using it to reduce pain and dramatically speed up recovery. Personally, I find that when I wear Earthing sandals on long walks in nature or even just around town, I feel more energized and cheerful.

Travel Pillow – In the old days I could be seen wheeling the largest overhead bag I could get away with and always with a big U-shaped pillow attached to it. Now just distant memories, I no longer use a wheeled bag and hadn’t taken along a pillow in decades. My neck ain’t happy about it. I like to sleep as much as possible while flying, but hate waking up with my chin on my chest and my neck all tweaked out of shape. But I still refused to bring along a pillow. That is until I found the NotNodi travel pillow. This clever little fellow compacts down to just 7” x 3”, leaves your neck free from sweating, and yet keeps you from the dreaded mid-flight head flop.

There is a long stretch of fabric that sits between your back and your seat. It’s attached to a small cushion that goes behind your neck. And attached to that is a headband that goes around your forehead. You can move around freely and even get up and walk around the plane without any trouble, but when you lean back in your seat it keeps your head from flopping around. You can also get it with a blackout eye mask for us light-sensitive types. But for the self-conscious traveler, you can just use your favorite baseball cap and attach it to the NotNodi in place of the headband. It’s a clever, compact solution to getting a decent sleep on a long flight.

With the right bag and accessories, I’m able to travel the world for weeks on end all with just a personal sized container. It’s easier to get around with less stuff and I can let the contents of the overhead bins shift as much as they like. Remember, the goal isn’t to see how much you can cram into a small space, but to free yourself from the burden of excess. By embracing this philosophy and equipping yourself with the right tools, you’ll discover a new level of freedom in your travels. So pack smart, travel light, and let your adventures, not your luggage, define your journey.