Emmi Versus the Spiderman from Todd Randolph on Vimeo.

Over an espresso con panna this past weekend, a girlfriend confessed her fight or flight response to her date. In hushed tones she whispered that they had made it back to her place when he prematurely disrobed and revealed, not the classic boxer brief or trunk, but a fluorescent smiley face print thong.

After the lengthy intervals of laughter subsided, I wondered, “Where does a guy get a dayglo men’s thong in our increasingly stylish, yet still puritanically- influenced city of Boston?”  The answer was as close as the Marshall’s on Boylston street.  I took photos pretending to ignore the sales associates’ glare.  Now, while I’ve seen bad underwear on the racks before, it never occurred to me that they actually left the store with someone.  I always figured underwear like that ended up getting recycled into sponges or melted down into a Snuggie.  But clearly men out there are buying them, so just in case you ever wonder if you should expand your skivvies style, do not under any circumstances try these.

The last thing women want to find out about you at that oh-so-fragile, tender moment - the unveiling of your stylish attire- is that your stairway to heaven leads straight to Tacky Town.

If you’re cardigan shows cleavage, opt for a higher neck line, or a push-up bra.

A guy who wears a bow-tie could never hit a girl, right? Photo by PETER STONE/CNN  

Dressing for a public apology is different from dressing for any other public appearance because you want to portray respect, humility, and remorse rather than power and authority.  But it is equally distasteful to go overboard trying to appear gentile and dapper because it is easy to cross the line to mockery.

This is particularly true if you’re apologizing for the merciless beating a petite, defenseless woman who is a passenger in your rented Lamborghini.

Let’s hope you never find yourself having to make a public show of remorse, especially for such a heinous and distasteful act, but just in case the media does catch on to your Brazilian mistress, performance enhancing drug usage, or acceptance of bribes, here’s what to wear. 

Unlike your actions your attire should be straightforward and understated.  It should not scream any message to your viewing public.  Your best choice is a dark grey wool suit; not black – you don’t want to appear to be dressing for your own funeral.  Pair it with a white shirt and a grey silk tie with a simple, subdued pattern.  

Avoid bright colors.  A tone on tone color scheme is unobtrusive and dignified, and provides just the backdrop you want while ingratiating yourself to the public again.  Lastly, wearing anything with even a hint of flashiness will not help your case, like too much bling or say, a big Robbin’s egg blue bow-tie. 

A: Yes, this:

When it comes to swim trunks, avoid wearing anything too tight, flashy, or revealing.

Cyclops is angry.  Who could blame him?  His entire life he’s been subjugated to wearing two eye sunglasses.  But no more!  Designer Martin Margiela’s keen ‘futuristic’ design finally allows Cyclops the dignity he deserves.  Now he just needs some size 62 Addidas kicks to complete the look.

This ad is just too good to leave back in the 70s.  For those of you who had forgotten that America went through a period when an adult onesie signified “sex machine,” I present to you:  The Big Zip.  This Bee Gees meets Scarface meets gas station attendant getup has a spot on marketing message too, promising to transform you into a “walking turn on” because it “fits so tight it shows all you’ve got.”  Or perhaps one also has to carry around a giant wooden staff for maximum effect.

Think a Hawaiian shirt is just the thing to show off your playful side at cookouts this summer?  Think again.  Women generally hate these billowy bright mini muumuus.  Why?  Look at the fit.  Most men already tend to wear clothing that’s too large for their frame. Compounding the tent tendency by sporting a ginourmous loud, garish Hawaiian shirt, (no matter how luau-festive it looks merchandised at the store) is a major mistake - step back or you will be sucked into a major Tsunami of tacky.

If you’re wondering when it is appropriate to break out that wicked cool party shirt that makes you feel like you’ve got an express ticket to Margaritaville.  Here’s your checklist.

Are you:

A. In Hawaii or similar tropical island?

B. On a cruise with a bunch of retirees?

C. Having game night with your charity bowling league?

D. Playing shuffleboard with your grandparents in Boca?

Unless you answer “yes” to one of these questions, put the shirt down and walk away.  There are so many better fitting, smart casual summer shirts out there for men.  For example – the linen gingham plaid button down, priced at $19 from H&M in the picture above is just one of the many options available to you.  So, fun guy, unless your purpose is to provide women with a warning to run, there is simply no reason to publicly punish yourself (and others) by wearing giant palm trees, surfer stick figures or dolphins mating.