Help me dress to impress
 

One of my resolutions this year has been to get out of my shell a little more and socialize. I've been doing pretty good, for me, anyway. Back when the weather was cooler, I was getting lots of compliments on the jackets and fedoras. (I think a lot of the good reviews were from people just stunned that I was actually trying, instead of being my usual wallflower self.) Anyway, I like the attention. And pretty people talk to me. It's keen. But here's my problem. It's freakin' sweltering here in Florida, and I have a couple of social events coming up. Jackets seem not only silly but downright painful to contemplate. So, how does a 45 y.o. schlub create a late summer look that is cheap but charming? I'm counting on your assembled wisdom. (I have no fashion sense of my own whatsoever.)

I know this sounds counter intuitive with the heat, and not having been in Florida-level humidity in quite some time I might be wrong - but layering with cotton under shirts is a good way to go. As long ad you're sticking with short sleeves, a cotton undershirt with a light weight button down on top, looks great, and keeps the perspiration out of sight. I favor a solid color under shirt with a casual patterned linen (or faux linen) on top. And you can't go wrong with jeans (but then long pants in heat never really bother me, ymmv). Gap makes the most comfortable, best fitting jeans I've ever owned (the classic 1955s), worth the cost.

I have always found a bit of a retro look makes people stop and smile (plus it never goes out of style) make sure to only 'do' eras before you were more than a tot (mid 60's is our cutoff point). Look to rat pack and earlier looks. So for summer heat nothing is cooler than rayon & linen think about investing in a linen summer suit, if you go to burlington coat factory or ross that type of store -do NOT pay retail, you never get your money's worth. For a more casual look think rayon shirts and if you go for shorts make sure they are simply styled, cargo shorts are unattractive on anyone. Wear retro sneaks like converse is colors you like, if you wear sandals make sure they are not make of plastic unless you are at the beach . . . . if you wear jeans, again go with retro styles, no funny washes or weird cuts, a tiny bit loose is always better than too tight.
/rant

I'm a sucker for a man in jeans and a button down top.

Also, it may sound bizarre but check out pictures of Jeffrey Donovan and Bruce Campbell from Burn Notice. They film in Miami.

Bruce

Jeffrey

Group

You left out Gabrielle Anwar

I'd like to help you but I dress like a homeless lesbian.

:D

Why would Flippy want to dress like her?

And I didn't leave her out, she's in the group shot.

Plus, Gabrielle Anwar isn't very attractive.

Linen - and a Summer straw fedora.

I've been searching for a good linen summer jacket for awhile now

There are moments when she looks hot, but yeah, I mostly agree with you (too skinny for my tastes). I think sometimes her sexiness in in her actions, not her looks.