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Have you ever considered a messenger bag ? I love em and they are so conveinent and they hold alot of stuff too .
I was thinking the same, PL. I have a few, very nice leather messenger bags, each with 1 very sturdy, wide, adjustable strap. I began collecting them when I lived in London/Boston/NYC & carried as much stuff as the OP, because I was on public transit for 2-4 hours/day... carried a book, umbrella, gloves, scarf, sometimes a light/suit jacket, cap/hat, coffee thermos, lunch thermos... all the accoutrements we underground, urban dwellers in rainy, cold, snowy locales carry, who are away from home from 7am-7pm+). All were happily, surprising finds at local charity shops... it seems, over the past few years many are getting rid of heavier leather bags (once used for lugging laptops from office to home) in lieu of the nice, light, neoprene, protective covers now available.
In addition, the OP might like to look look at larger satchel/tote bags with 2 handles (which sometimes also have a crossbody strap), as well. This way, the stress of the heavy contents will be divided & not all relying upon 1 strap.
I have several of these in leather... also bought from charity shops. My only fuss with them is most don't properly zipper, although some do... not a great option if on public transit or in big-city crowds.
And, everyone may already be aware, but, if a strap breaks, anyone who does alterations should be able to fix it. I had a strap break on a leather crossbody bag, stretched to the max on a regular basis. It was sewn by a local cobbler for $10 & hasn't broken since. He said he fortified it (I believe he placed some sort of material in-between the leather overlap), since I was using it regularly. It's my go-to bag, because it's roomy but thinner & great for subway use or if I'm going bargain shopping & want to slide it from front to back whilst rummaging through bins. I don't use public transit any longer (thank goodness), but it's still my favorite bag.
Good luck!
P.S. Thank you Southern Belle on conditioner info & Jade for all your info on bags/cleaning!
May I ask those of you with leather bags, how do you take care of them? Does anyone use those bottles of leather polish for a once/yr sprucing up? Or, just a wipe down if rain, snow or any moisture has gotten onto the bag?
Honestly, and I feel a little sheepish about this - I do not do very much at all. And they really look good! And stylish! My now 17 year old daughter and I bought the last ones - and we both still use them.
One of my cats peed on one - no fault of the bag - and I had it cleaned at a local dry cleaner. It came our well, without any bad odor.
I'm not sure that I'd call "Coach" a designer. I just think that they make good bags. Not overly trendy or overly preppy - in a style that can fit all.
I like Coach and Fossil.
Fossil uses heavy-duty leather but they're really nice bags.
I've had my Coach and Fossil bags for years and they're still holding up.
Women's Tumi bags! I have had all of my Tumi bags for over five years and they all look new.
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I was thinking the same, PL. I have a few, very nice leather messenger bags, each with 1 very sturdy, wide, adjustable strap. I began collecting them when I lived in London/Boston/NYC & carried as much stuff as the OP, because I was on public transit for 2-4 hours/day... carried a book, umbrella, gloves, scarf, sometimes a light/suit jacket, cap/hat, coffee thermos, lunch thermos... all the accoutrements we underground, urban dwellers in rainy, cold, snowy locales carry, who are away from home from 7am-7pm+). All were happily, surprising finds at local charity shops... it seems, over the past few years many are getting rid of heavier leather bags (once used for lugging laptops from office to home) in lieu of the nice, light, neoprene, protective covers now available. 
