To celebrate my 50th (tomorrow), I've booked a trip to Chicago for the first weekend of October. I plan on attempting to reconnect with family that I haven't seen in years, and I want to visit some places I remember enjoying when I was much younger. I live in the Austin, TX area, and the shopping here is dismal. Most of the major stores are nothing more than outlets, and boutiques are rare. I'm looking for suggestions on good shopping for men's fashion. I'm not going all out for North Shore bespoke, mind you, but I do want options with quality. Clothes, hats, shoes, accessories...I'm open to all suggestions. What are some places you enjoy? As a bonus, any restaurants, food vendors, coffee houses, etc. you'd recommend? It's been a minute since I've had real Chicago pizza. Thanks! I'm sure the weather will be significantly different from Texas. Having lived in Illinois and Alaska as well, I'd like to think I'm not a huge wimp when it comes to cold! Still, I plan on taking some light clothes to keep me warm in the evenings (and there's an architecture cruise I plan to take which I'm sure will require an extra layer).

I’ve been trying to find a way to carry my keys. I’ve pared it down to just 3 keys and alarm fob. Any suggestions?

Any suggestions for light material Sports Coats (lining) for hot desert climates like El Paso, Texas? Brands, etc. Thanks

Took a trip to Bandera, Texas, known as the "Cowboy Capital of the World. Saw this scene and I had to share it with everyone. Gives a new meaning to “saddle up” to the bar. I wore a simple pair of blue jeans, black Ariat shirt , black Stetson, black Invicta watch and my alligator and goat shin boots.

Light blue linen blend shirt, olive chinos, brown minimalist sneakers, Dobbs fedora, Seiko Samurai, and Washburn WG7S-O acoustic guitar I have in the office as a practice, arranging and noodling axe. If you're looking for productive, stimulating ways to spend your free time, learn to play guitar. Playing music is therapeutic, calming, and keeps your mind sharp! Nobody is "too old" to pick up a guitar and learn 3 or 4 open chords you can quickly play songs with. These days there is no need for "lessons," either. There are hundreds of videos online to help you get started, pick an instrument, tune & maintain it, and begin to play. I highly encourage it.