Hi, OP! I've just spend weeeeeks looking into the exact same query. Here's what I found, if it's at all helpful. Note: A lot comes down to what look you prefer. The Cotopaxi Todo is 8L and comes in various colors, including black. Simple and light. Low cost. Can be found for under 60. The Cotopaxi Chasqui is 13 L and comes in various colors (look at multiple vendors and eBay to see options). It has pull handles on 3 sides (which I personally like a lot). Can be found for 60-80 bucks. Chrome makes the Kadet Max, which would have a lot in common with your present little guy but otherwise gives you MUCH more size to work with without being too bulky for transit. Cost new is 110-150. Aer makes some packs and slings that would also meet your criteria; prices range but expect 90-130. If you're into casual looks, both Patagonia and Osprey make super light slings. Topo also makes some interesting options, if you like their look. I suppose it's a little polarizing -- lots of colors and textures and whatnot. If you want something that's a mix of practical and pretty, Timbuk2 has a number of great smaller bags and slings. I've had a lot of their bags over time and can testify to their quality. They aren't always the "-est" in any category - not the lightest, not the cheapest, etc. -- but I find that they blend fashion and function incredibly well. I really like their Mini Castle Sling and also their Mini Prospect Backpack for a small but functional personal item that can be worn on the town too. All of the above are pretty casual (the Aer city sling can look a little "cooler" though). There are some other brands like PacSafe and Travelon who make slings, but I find they're a little bulky and usually pretty expensive for what you get. Because I didn't need my sling to be my day bag (I usually just carry a small purse), I opted for the Osprey Transporter Boarding Bag (on sale at REI.. with points added, I got it for $45 which is insane) because I simply wanted hands free / something that could be my personal item whether I'm one-bagging in a backpack or with a rollerbag. (PS: A lot of people say Tom Binh bags. I fully appreciate their utilitarian styling but I find them to be the ugliest damn super expensive things on the planet and could not bring myself to look into payind $300 for a sling that looks like something I could have bought thrifted from the 90s... and it would have been ugly even in the 90s...but they also make some bags that meet your criteria if you're interested.) Answer from wiLd_p0tat0es on reddit.com