Anyone looking for a top quality, durable, go anywhere, manly bag should look at the
Tilley Intrepid Bag based on a WWII utility bag. It isn't cheap for sure at $300 bucks however it is an amazingly strong bag that should last decades of hard use.
Had looked at them for years then I bought one 4 years ago as a diaper bag when my son was born and laughingly said it was for him as a good excuse for the wife. After 4 years of use as a baby/diaper bag it's also served as a quick shopping bag, gym bag, weekend woods bag (including Canadian winter camping), overnight away bag and general travel bag. Smart packets can live out of a bag like this for days.
While there are no outside pockets like in many gun purses designed for women it shouldn't be that hard for a good tailor or local leather worker to modify. I prefer to carry on my person however there have been times when this is better.. Beach trips, doctor visits, just to toss out a few. I carry cross body meaning strap on my left shoulder and bag on my right side making it pretty much impossible for a snatch and grab.
I know it's not for everyone and is pricey (though have you seen the prices of some women's purses!) however it's a great option for a rugged stylish man bag. I've been wearing their Tilley hats for 20 years now and still have the original one I bought along with a few newer ones. I know their quality is top notch. Made in Canada, eh!