This is an easy collegiate look you can pull off with minimal effort. First get this shirt by J.Crew. Dennis is wearing a varsity jacket in the picture. I however have a hard time taking anyone serious wearing those things. This baseball jacket by Rugby covers the look without bringing patches into the mix. The red, white and blue might give you too much of an americana problem but it just is a good color combo. It comes in green too if you cant handle it though.
Finish this look off with slim fitting light weight chinos or dark 501's and some chukkas. A clean shave and a nice haircut wouldn't kill ya either.
Don't have a 9-5? I don't care, dressing well doesn't hurt anyone. Wear this out for cocktails or dancing. Too hot? Here in San Francisco it's cold at night. I hate wearing winter coats in the summer. A suit with a shirt and tie is an easy way to combat bulky coats and hideous scarfs. That's right I said it, scarfs off fools.
Although this tie is different colors then Dennis' I think it will modernize and summerize your look. Get it at J.Crew. Please resist the urge to get a collar pin with bulldog heads at the ends. Your wearing a collar pin that's enough kitsch on it's own. Keep it simple with this one offered by Nordstrom. And a lighter weight suit from J.Crew should keep you from complaining about heat.
Wear this look only if you can pull it off without looking like your wearing a costume. You know who you are.
This is an awesome Stetson hat I found for sale at Sheplers. This smaller brim is best for urban wear. Don't skimp on hats people. This shirt does away with tired roses on your western while staying old school. Plus, I prefer a flat pocket for bolo tie wearin'. It's a Panhandle Slims.
Please keep it simple with the bolo tie. You don't need a coyote howling at the moon, a simple stone will do. Here's one from Sheplers.
Combine these two Hopper's by adding this Pendleton coat. Don't you want it anyway? Kills me.
This is easy. Stetson black felt hat. Sharks tooth! You can find one I know you can. Levis denim shirt, Levis denim jacket. Various beaded necklaces? Go to your local hippy store.