I always have a pocket knife on me. Amazing in how much you will actually use it if it’s always on you. Ever since I was a search and rescue swimmer, staples on me are a mechanical or quality quartz watch and a pocket knife. these two items can be generational and something you hand down to your kids. They patina and scratch as you make it yours. Other items noteworthy: If you get a knife, get a quality sharpening system and not some cheap one that will ruin your blades Fitness tracker A few high quality fragrances for every occasion you do, go to office, lounging, fall/winter, spring/summer, gym, date nights, lounging at home, fun scent, etc. A nice silver or gold chain necklace A couple nice bracelets A signet ring I have my grandfathers signet ring and this was the item that was used to identify his body after he passed away in a plane crash so this is another item that can be passed down. I’ll never forget when my mom gave me this. Good cuff links Tie bar If you wear dress shirts you must have shirt stays, I prefer the stirrup ones Quality leather belt and shoes Exercise gear, UNRL makes the best and shoes I like Brooks Quality pen Pocket flashlight First aid kit in areas you may need them like different levels of home and every vehicle you own, especially if you have a four wheeler or boat. Basic survival kit geared towards your environment, I keep one in both my cars A variety of tools, different saws for home improvement, hammer, ratchet / wrench sets, screwdrivers, power drill/power hammer, air compressor and nail guns for framing and finishing, sanders, routers, levels, basic tools to do most home improvements within your capabilities, I’ll add in paint equipment like a nice sprayer roller extension rod sanding block, paint trays, high quality brush like Purdy or equivalent. If you have training at least one firearm, suggest a few if you can afford, .22 lr, 9mm handgun, ar-15 style rifle and a shotgun, hunting rifle caliber if you hunt. Not necessary but once you get to a point of financial stability, the number one thing that makes me feel manly is having a manual transmission sports car. I absolutely love my Shelby GT-500, purchased it used and it’s an older generation but man it just makes me feel good every time I take it out for a Sunday drive on a nice day.