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From my experiences in Mid Town...there are some patio bars like woodrows previously mentioned that allow shorts/flippy floppies etc however many of them, at night, require jeans or slacks and do not smile upon tennis shoes/sandals.
if you want to make sure you have zero problems getting in somewhere, i recommend telling everyone to wear jeans.
nobody petal parties in midtown...not that i have ever seen, that is a washington thing.
I wouldnt use the wave...i would just get an uber black...once in midtown you can walk to most bars...and uber can take you to treasures...dont think the wave goes that way
Almost all places allow shorts if wearing nice dress shoes etc with them (no tennis shoes)
Lots of people petal party in midtown but it would be miserable in July.
I would go UberXL if having up to 6 people, anything less than 4 use UbverX. Super cheap way to get lots of people around and like I said above I would go from dinner to downtown for drinks then head to midtown for last 2hrs or so of the night.