Taking a trip to Chicago · Real Men Real Style Community

Taking a trip to Chicago

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).

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