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Posts by msulinski

Khakis or any kind of tan to mid brown would be fine. Mid gray and lighter would work too.
They deliver on Saturdays instead of Mondays.
Wait, you want them to taper the pants even more than they already are? SS pants already have a very narrow leg opening.
Socks with loafers are perfectly fine. If you are wearing them with long pants in a non-tropical setting, they are certainly preferred. Those loafers specifically seem to be a bit more on the formal side (looks like a low profile leather sole, no contrast stitching). If you wear a more casual pair with shorts, then skip the socks. For sock color, it really depends on the color of your pants.
I work in Manhattan also. The walks can be brutal some days. In addition to cotton, you could try tropical weight wool. I have a suit made in Holland and Sherry Crispaire that is 7.5 oz and unlined. It is probably the coolest-wearing suit I own. On the way home, I would loosen the tie and open the top shirt button. There seems to be some debate over undershirts. I am in the camp that believes they help. I have a bunch of Uniqlo Airism shirts that are supposedly designed...
As for shoes with shorts, I have a hard time figuring this out. So far I have come up with Allen Edmonds Sanibel and Preston. Any other recommendations?
I think you are better off getting 2 pairs. One for casual suits/sport coats/chinos, and a completely different pair for shorts.
There is no one shoe that does everything well. I can't think of a single shoe that works well with a suit or with shorts. Really though, why would there be? These looks are at the extreme ends of the formality spectrum.
I wouldn't wearing straps with shorts
 I agree. Even if your jacket looks good unbuttoned, it will look even better buttoned.
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