A messenger bag was fine for the daily drive to work, but when I was traveling with a 17” MacBook Pro, a Nikon DSLR, lenses, power brick, etc… I had a backache after a few hours. Since I was in San Francisco I headed over to Timbuktu’s store and bought a backpack. I moved everything to the backpack before I left the store and it was instant relief. I haven’t had any more problems with back pain since switching to backpacks. I have some smaller messenger bags and slings for quick trips, but they don’t get much use.
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Backpacks are said to be best for your back. Second only, apparently, to one on the back and a counterbalancing one on the front.
I don’t see myself carrying much on the front, though I do have a small “bum bag” / “fanny pack” for going through airports. (REALLY convenient, it turns out.)
What color do you have and what is the color of the interior lining? I picked up the gray one recently and the lining there is orange, which is a no go for me.
The interior is grey with red accents, and the laptop section lining is orange, which is my favorite color 
How about contacting Incase to ask if they will repair it? I have a Tom Bihn medium Cafe bag, and the clip broke. I emailed them about this some years later and they repaired it for me. After email discussion, I also ordered a “Freudian Slip” insert / organizer for it. This also fits in the original Ristretto which I got for my original iPad.
My two daily carry backpacks are a Swissgear for larger loads and a Booq which can carry a 15" MBP but has less internal space and forces me not to carry a heavy load. Sadly Booq went out of business and very few of their products are still available (https://sozodistributing.com/brands/Booq.html ).
I have been on a bag search for several years, and I finally landed on the Tom Bihn Synapse 25 a few months ago.
I have used Timbuk2 bags for a while and those were really good as well. I had the large classic messenger and then most recently had the Rouge Backpack (rolltop style bag with plenty of room inside for anything you want.
I ended up with the TB bag because I wanted a little more organization than I was getting from my Timbuk2 bag. I have been beyond happy with the Synapse 25. It carries my MBP, IPad Pro, tons of accessories, notebooks, power bricks, etc. I can tell that I love the Synapse 25 because I haven’t searched online for a new bag since I started using the S25 3 months ago! Haha.
One of my favorite features of the Timbuk2 Command bag is that it is as comfortable as a backpack if I sling the strap crossbody, with the strap on my left shoulder and bag above my right hip, or behind me.
I just think a messenger bag looks better.
I’m TSA Pre. Shoes, belt and jacket stay on. Before I even get in the security line, wallet, phone, keys and AirPods go in an exterior pocket of the Timbuk2 bag. If I’m outbound from home, keys stay in that pocket until I return.
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Same here, I saved and saved for Saddleback leather briefcase. It weighs a ton.
Now I carry a canvas Fishpond Boulder Briefcase.
Canvas - the first technical fabric…
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Buying a new backpack/bag is the worst…
I am looking for something to carry:
- a 15" laptop
- office stuff (pens,…)
- sometimes a camera (DSLR)
- sometimes gym stuff
And I want it to be:
- a backpack
- weatherproof
- good-looking (not look like a school bag, not “tactical”, …)
I have excellent backpacks for camera gear, but I miss a good one just for “daily office use”.
I agree. My EDC for decades was a series of Lands End canvas briefcases (sadly that model is now discontinued). I wore out a couple, and one was “borrowed” and never returned by a divisional vice-president. Stuff it with papers, books, or hardware, if you could close the zipper it could handle the weight.
I replaced my last one with a 34L backpack a few years ago but it is still my favorite “personal item” for travel.
Thanks. I actually wrote to Incase yesteday to see if they can repair it. I don’t want to add to the waste stream if I don’t have too and its a fine product otherwise in great shape.
I did hear back from Incase and they no longer offer a repair option for the bag.
My favorite Waterfield bag is their Sutter Tech Sling. https://www.sfbags.com/collections/slings/products/tech-sling-bag?variant=17563979481145 . I can carry my original iPad Pro, iPad Air 10.5, and a keyboard, along with my Roost stand and various chargers and cables.
I have 3 bags that I really like. As a bit of background, part of my gig is event photography, so these bags cater to expensive gear and lens organization — but you could organize these however you want.
Quick list:
- Ona Brixton. After a car accident a few years ago where I had a minor shoulder injury, this is the bag I wear the least. It’s a messenger bag, so it’s only good for those of us with tank shoulders. But I’ve had it for a million years and it’s a tank. Not completely waterproof.
- Peak Design Every Day Backpack. The small size is good for most people, I think, although I wish I had the large. I use this 90% of the time I’m out and about. It’s darn near perfect. It has survived African deserts and tropical storms, and kept camera gear and laptops dry and safe in there the whole time. I can’t recommend it enough.
- Lowepro Tactic 450 AW II. (I’d like to link it, but I’m new here — hi! — and only allowed two links per post.) This bag holds a ton of gear. It’s my go-to if I’ve got a big client shoot. I can’t recommend this to everybody, but if you travel a lot, this might be exactly what you’re looking for. Insanely comfortable. I can strap 20lbs of camera gear to my back and not feel the strain for hours. Only bummer is that you need to put a separate cover on if it’s raining (which is included).
The Everyday Backpack is probably the best place to start for most people, in my opinion. I’ve hiked mountains with and done all sorts of crazy stuff with it in multiple continents, and even the small one could hold my camera and a couple lenses, along with multiple sweaters, a laptop, water bottles, and more. But it’s still sleek for urban wear and professional enough for office work. A genuine workhorse bag. I love it.
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I got one from Chrome Industires. The build quality is excellent.
Some are fully water-proof roll-tops and some are just partially water-proof. I myself have and older Bravo bag. If it is heavily raining I will move my tech from the front pocket to the large roll-top compartment, which is waterproof.
I would now probably go for the Volcano.
I prefer my laptop compartment to be on the outside, because I cycle a lot in a very sportive position. If I carry other heavy stuff in my backpack (books, bottles etc.) their weight won’t be resting on my laptop.
For some this is a security risk, but as soon as it gets crowded in public transport the bag swings to the side with my arm over it.
I had a messanger bag from them. As you said, excellent quality.
Same here. I have shoes stored in my office to change from the bike shoes into them.
But I cycle into work when not too much is going on (external meetings). Often I have too much stuff with me, need to move between venues, etc. You really need several bags/backpacks… 
And since I am into photography, I already have some dedicated for that.
I love my Baron Fig Venture Slimline Backpack. Never seen it on a rainy day but it fits so much, doesn’t weigh me down, fits comfortably & I feel kinda snazzy in it. I am wondering if I can rub beeswax in it. Anyone try this yet?