Edit: Updated title. Hello all. Please forgive me starting a whole brand spankin' new thread just to field my own question. But, I'm doing it because I think the question is specific enough, and I'm just needing some advise from those of you who have real world experience with my options. I'm really looking forward to hands free walking. My budget consists of $150 of Cabela's gift cards. I already have a Rush 72 clone Get Home Bag in the Truck. Question: Should I buy a Moab 10 sling bag, or Covrt 18 backpack? Will the Moab 10's strap be long enough for a tall guy? I work in a financial operations office that's business casual. Ages in the office run from early 20s to nearing retirement. I'm technically bridging the gap between Baby Boomer and Gen X. I'm also tall (6'4"), and not skinny. I recently noticed that no one carries a big ol' lunch cooler like mine. Instead, I see small sacks, messenger bags, duffles, and small insulated lunch coolers (usually soft sided). I'm thinking that carrying my cooler makes me look like I'm going on a picnic. I picked it up because I take leftovers in glass containers and they are heavy. I can limit the glass to just one, and go plastic for my salad. The big cooler is on the right. An example of a glass container in front with a Vic Explorer for scale reference. My wife's Maxcool lunch cooler is on the left. Current "EDC" set up: Food goes inside the cooler. I carry my computer glasses in one side mesh pocket. In the front zipper pocket I carry: 1. Prescription pills 2. Bottle of Zyrtec 3. Bottle of nasal spray (allergies) 4. Victorinox Waiter 5. Plastic eating utensiles 6. Glasses cleaning clothe 7. Salene eye drops Top desk drawer: Vic Classic SD Chapstick Second desk drawer: Condor pocket organizer - AA flashlight Leatherman 1st Gen multitool First Aid goodies Snack bar 7" pry bar Write In The Rain pad Pens N95 mask I keep the Condor there in case we have a disaster, or fire drill. I'm on the fire safety team and would assist in building evacs. When we have a fire drill, I grab the Condor and take it with me. What I'd like the capacity to carry in a new lunch/EDC: Lunch (probably in a thin bag/neoprene, to go in a MOAB 10 or COVRT 18) The contents of the Condor so it's always with me. Small umbrella or light wind shell (Colorado Springs has almost daily afternoon thunderstorms, then sun again) Hat and gloves (in winter) Discreet change of clothes (simple skivies, maybe a shirt) Contents of my cooler zip pocket Sunglasses Computer glasses case Maybe a water bottle (think Stanley) Hands free carry The MOAB 10 should be able to handle all of this, except maybe the water bottle. I'm concerned that the strap would not be long enough for me. I could also use this for day trips such as to the zoo, short hikes, etc. Pros: Smaller, hands free carry option. Sling pack is more secure in public spaces. There won't be tons of unused space. Only $100 (allows me to get other goodies and stay within budget). Cons: Too tacticool for a business office (would have to get black). Water bottle may not fit in CCW pocket and would have to go inside. May not carry well with heavier glass container full of lunch. Won't carry a laptop (not a consistent need). The COVRT 18 should be ok for my taller frame and carry everything I need plus more. Pros: Large enough. Has two water bottle holders. Less tacticool with discreet MOLLE. Can carry my large laptop (not a consistent need). Would work great for at a theme park or zoo for carrying the family's junk. More color options. Would work well for day hikes. Cons: $130 (not much room for extra goodies). Maybe too large for office EDC (if left on desk, would stand up too tall and could be a distraction). One strap carry would require holding with a hand (no hands free carry). May look too much like something a college student would carry. It's not something different. So, what's input? I'd really like not to have a full backpack, but am willing too, especially since it could be used outside of work. But, the idea of hands free carry and simply throwing the sling bag over my head is attractive to me. I'm just concerned that the MOAB won't carry well, will have a short strap that will make it carry way too high on me, and may look to tactical for an office. It seems like the fabric of the MOAB would hold its shape better that the COVRT's thinner material would. Please let me have it! Bring on the knowledge! Bring on the opinions! Bring on the socially interactive banter, and bestow on me some advice! Thanks!