I’ve been writing a lot of emails advising people on bag purchases and pairing. Which I realize now is a completely untapped market with potentially billions of dollars at stake for me. I’ll fill that void. My goal here is to provide an everyday “work” carry option, as well as a travel option, both keeping in mind different styles of dress codes. Unfortunately, this is aimed primarily at men, as I can’t intelligently speak to women’s fashion at all.

Each category has a few pairing options — pick what calls to you. I’ll note my setup at the end. Godspeed.

Everyday Carry and Travel Pairing Tips

I do have a few general tips which may help everyone when trying to decide on a bag setup. Here are those in no particular order:

Never carry two backpacks. You’ll look totally nerdy and be miserable trying to carry them. We’ve all seen that person in the airport with a backpack on their back and another on their front — please don’t do this. Terrible.

However, two shoulder bags is fine-ish. It’s never easy to carry two shoulder bags at once, but you can typically manage it without looking ridiculous or wanting to swear off travel forever. It’s not ideal, but it can work.

That said: one shoulder bag and one backpack is best. Doesn’t matter which is which (daily bag versus travel sized bag) but if you need two bags make sure they generally don’t utilize the same method of carrying. Most people typically are comfortable with a shoulder bag at one side of their body only — and you can still do that if you wear a backpack for your other bag. I feel like this tip really is bigger than you might realize based solely on the insanity I see in airports.

Roller bags are dumb. Yeah I know yours is clearly the greatest, but seriously fuck these bags. There’s only one reason to use them: it was a last resort. They are a huge pain in the ass to move from place to place, and they actually tend to hold fewer items than other options. They are heavy and cumbersome, and actually kind of gross if you think about the literal shit you probably wheel them through. I’m willing to bet if you try traveling without a roller bag one time, you’ll see the light.

Your pairing needs to look good together, so you don’t look disheveled when traveling with both. In other words: look like you had some modicum of forethought to the fact that these two bags might be one day used at the same time as each other.

Most packable bags fall into one of two categories: they don’t pack up very small, or they are utter shit to carry. There do exist some that straddle both well, but the caveats are many.

Lastly: one bag fitting inside the other is sweet, but nearly impossible to accomplish. And then, when you do accomplish it, it can be annoying when you are on the plane because everything you need is above you in your bag which is inside your other bag, and you don’t want to be that person rummaging through their shit while you await takeoff.

Take the above or leave them, they are just my tips. Not rules or anything.

Dumb Rules

These are the rules:

Canvas sucks for bags, but waxed canvas is sweet. If there’s no layer of wax on your canvas, you should rethink the bag.

Figure out the size of bag you like, based on what you have already. The key metrics: height of the bag, and width of the bag. Whether shoulder or backpack, sort out what feels too big for you and what feels too small for you. For me I know I can handle a backpack that is about 18” – 22.5” tall and about 12.5” wide at most. For shoulder bags I don’t like anything that is longer than about 15” and taller than about 12”. Having that knowledge allows me to quickly weed out bags that likely won’t fit me or work for me.

If given a choice, always opt for slim over fat bags. For example if one bag is 16x10x6, and another is 17x11x4, go with the thinner bag. Thickness is uncomfortable to carry and gets in the way — a larger footprint is almost always easier to deal with than a fat sack of crap.

Backpacks are more better than anything else and I am pretty certain that Ben Franklin, or Newton, or Einstein (someone like that) said that. It’s just science.

What you carry in your bag dictates everything you need in the bag. Figure out what you carry first. That will dictate what size bag you need.

Always try to keep your bag 20% empty, that will allow for eventualities of life. So when you add up what size you need for your normal stuff, add another 20% to that. That’s the size bag you need.

Always optimize for the bag you use the most. So buy the daily carry bag in the setup you want first, if what you do most if use the daily carry bag. If you travel nonstop, then perhaps you optimize your setup for that bag first and foremost.

Ok, now on to the bags…

Business Casual

If you generally exist with a business casual wardrobe, the key for you is going to be finding gear that looks non-cheap. This can be accomplished two ways: heritage materials and brands, or “fancier” looking technical bags. Here’s my suggestions for this type of bag:

Aer’s Travel Pack with that shiny nylon on it that looks nice than standard nylon crap and pairing that with a classic waxed canvas shoulder bag. Like so:

Another option would be to get a vintage styled duffle bag for travel, and pairing that with a leather shoulder bag. Like so:

On the complete other end, you could get something like SDR’s D3 bag and pairing it with the insane Nomin backpack. If you can afford it it looks like so:

The key here, is to pick what fits your office environment and your clothing — since you likely carry your daily bag more than your travel bag. So choose the daily bag which best matches your style, and then find a good travel bag to pair with it. Remember pairing the bag carry methods is more important than the looks because you simply will not be carrying them both together that often.

Smart Casual to Casual

If the business casual section felt a little too formal, then ‘smart casual’ might actually be your style — it’s a thing, whatever. Here’s the category which I think most ‘tech’ workers are going to fit in, and generally the style I see most commonly in workplaces. Then again, what the hell do I know, I work from home.

GR1 26L or 21L, and a duffel bag are my top pick in the area. You can tone down a GR1 by picking one in the Steel or Navy colorways, then it looks less tacticool, however black is best. Get a matching duffel bag, particularly this one, and you are set. Like so:

Or, if you want something which is less rugged, but still will last a life time, a neat option is Tom Bihn. The Synapse 25 or 19 are fantastic backpacks, and when paired with the Road Buddy Duffel 36, a damn sweet pairing. Like so:

Or, you could still want something which feels lighter and ‘faster’, for that take a look at the SDR M1 shoulder bag, and I’d pair that with Triple Aught Design’s Meridan Transport Case. Like so:

The Anything Goes

I really picture the work from home groups here, or the people who truly work somewhere that it does not matter what they wear. Odd group, but hey, here we go.

The SDR Field Kit #2, Higashiyama and just that. Ok here me out for a moment. This is SDR’s 1M Hauly (designed to discretely carry $1 million dollars cash) with a collection of accessories for turning the bag into a daypack of sorts. At 20 liters it is not huge, but it’s really fucking cool. Look at it:

GORUCK GR2 and Bullet Ruck would be my next runner up combination. I’d get the 40L GR2 unless you are a smaller frame then the 34L, and pair it with the 15L Bullet. The Bullet will fit easily in the 40L and work as a makeshift packing cube when you travel, and the entire setup could carry your entire life. That Bullet though is ideal for coffee shop trips, no matter where in the world that coffee shop is. Like so:

Tom Bihn’s Shadow Guide would be my next pick. It’s actually big enough that some could travel with just it, but small and floppy enough that you can head out to a coffee shop without looking like a traveler. (Tom Bihn also told me that it is one of the few backpacks which carry those huge gaming laptops if that is your thing.) It’s also fucking sweet looking, look at this thing:

Bonus pick: This bag is one I know nothing about. But damn if it doesn’t look hawt. I mean, for real, I might need to buy this:

The Suit

This is the toughest of the lot because there’s no backpack which can really be worn with a suit, and still keep the look one should have when wearing a suit. So, I’ll do my best to give you some options, but note that the Business Casual section could also apply here depending on your environment and how suit, your suit is.

A classic briefcase with leather, paired with an even more classic weekender bag. In this case the traditional materials work in your favor to create a really complementary look to the suit. Like so:

You can also take a far more modern approach to it, with something that combines some elements that pull you back to traditional materials, but with a modern twist. A briefcase in leather but with modern sensibility, paired with a nylon shoulder travel bag. Like so:

Or, you can go completely technical in looks, but a fully modern twist on things. A shoulder satchel with a sleek travel bag. Like so:

The Budget Guide

Ok, so basically everything I have paired costs a lot of money, but not everyone has the money to spend. So allow me to now correct that. What I don’t want you to think is that these pairings are anything less than good. They are inexpensive, but not cheaply made. I have pretty much owned all these bags at some point, and still own and use some of them.

My go to setup and recommendation is a good travel backpack with a stellar lightweight shoulder bag. Like so:

Another great option is a lightweight backpack with a solid duffle. Like so:

Lastly, if you want to optimize for a really good daily carry with protection, and have great mobility when traveling you’ll want a more flexible travel duffle and an organized backpack. Like so:

My Setup

As you can likely guess, I have a huge collection of bags accumulated over a lot of time and reviewing. Right now I have about four setups that I rotate through for both daily use and travel. Here are those setups.

My primary setup is simply my GORUCK GR1. I alternate between a 21L and 26L (if I had to pick one, it’d be the 26L without a doubt). When I travel it is almost always the 26L, but when I am just going around for the day it is the 21L. That said, when I travel with two bags my setup is the 21L GR1 with Piorama A10 adjustable bag. That setup allows me to travel anywhere with any kit and have tons of space. The 21L is preferred when I have another larger bag because it fits very neatly under the seat in front of you on most planes, whereas the 26L sticks out enough to be annoying if your feet are larger.

Here’s three pretty common setups I carry for travel/work/play:

GR1 26L, my only bag for mid-length trips. (Before you ask, that’s a special edition GR1, which is why it has the extra goodies on it. I have two 26L GR1s and alternate between them solely depending on how many patches I want to utilize for that trip.

GR1 21L and A10 Duffle as my longer or bigger carry needs kit.

15L Bullet Ruck and A10 for family trips, where I don’t need to carry iPads to and from offices so I can have a smaller daily carry bag.

Other times if I am going for a trip that I need a lot of gear on, but I do not need much of a daily bag for I use the Tom Bihn Shadow Guide which is a killer looking backpack and pair that with my custom cuben fiber shoulder bag. Now, since you can’t get that shoulder bag, you should note that the size of that bag is based off Tom Bihn’s Daylight Briefcase which is a better bag for most people. This kit allows me to travel with one bag, but have a small bag for when I get to where I am going. The Shadow Guide is a fantastic size as an only bag if you need to pack bulkier stuff.

When I need to daily carry and look a bit more put together I forgo the backpacks and use the Filson Original Briefcase in Otter Green. I fucking love that bag.

Lastly, I do almost all coffee shop trips, and day excursions with the GORUCK Bullet Ruck 15L. It is such an ideally sized bag that it is a close contender to replace the GR1 as the best backpack out there. Close, but no cigar. The GR1 is still far more versatile and handles heavier loads of weight much better.

Hopefully this helps guide you as you seek to buy even more bags. You can never have too many.

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