I’ve been on this journey now for a while. Eight years since I retired from the military. If you were to just start with one outfit, what would it be. When I went into civilian government work, I was required to wear dress shirts, slacks and a tie. The tie requirement has gone away and I no longer wear the tie but I’m still wearing dress shirts and appropriate slacks. I guess my question has two answers for me. In the warmer months, I pair a nice polo with dress pants and sometimes jeans. I wear Chelsea boots a lot and try to pair my boots and belt with the outfit. When it starts to get cooler, I almost exclusively wear dress shirts, but sometimes change it up with Chelsea cowboy boots and jeans. So what is one great outfit to wear?

While visiting a local jeweler, my wife spotted a watch she absolutely loved. The sticker price was $395, but my inner WIS (Watch Idiot Savant) couldn’t resist doing a little reconnaissance first. Sure enough, I found the exact same watch online for $350. Armed with that bit of intelligence, I returned to the store and launched my opening salvo. “Is $395 your best price?” The sales associate didn’t even flinch. “Nope… I can do $340.” At that point I was already beating the online price, so I smiled and said, “Deal!” As we continued talking watches and swapping stories, a little rapport developed. While she was boxing up the watch, I casually asked, “Do you happen to offer a military discount?” “Yes, we do—and thank you for your service.” Just like that… another 10% vanished from the total. Final score: * MSRP: $395 * Negotiated price: $340 * Military discount: 10% * Final price: Just over $306 before tax. Not bad for a few minutes of friendly conversation. Watch collecting teaches patience, research, and timing. This time, all three paid off. Better yet, my wife walked away with a watch she genuinely loves, and I got the satisfaction of knowing the only thing sweeter than a new watch is getting one without paying full retail. I guess you could say this purchase was right on time