A: In order to stand out from the crowd, either dress up or down, but stick with one and do it all the way.  Of course, there is a little bit of wiggle room, but if you want to stand out, just don’t plant yourself right in the middle of the “formality” scale by wearing a structured blazer, dress shirt and dark blue denim.

I think the dress shirt/jeans combo is so popular because guys consider it to be that “in between” look.  They think (incorrectly) that by wearing a button down, they are dressing up, but by wearing jeans, they are also keeping it casual.  Their mistake is thinking that the shirt is the piece of the outfit that defines the formality.  In reality, the pieces of the outfit that define formality are actually the pants and shoes.  You could wear a suit jacket, a dress shirt and a tie, but if you wear shorts, it’s still a casual look.  Or maybe they’re doing it because everyone else is doing it.  Either way, don’t follow their lead. 

As for accessories, the idea here is minimalism: skip the belt.  The pocket square is up to you.  You can wear your watch, but only if it’s subtle. 

If you want to make the look more casual, skip the tie.  Or you can skip the jacket altogether and wear a vest instead—but only if all components of the suit are from the same suit (i.e. don’t wear a medium gray pants and a charcoal vest).  As always, fit is absolutely key.  If your suit doesn’t fit, you’ll look like you’re trying too hard.  Tom Ford (left) does it right, as always.

On the other hand, if you’re going to a place where dancing is central, dress up by dressing down.  I say this more for practicality rather than for style.  Wear jeans, but mix it up by wearing jeans that aren’t blue.  A great pair of gray jeans can go a long way.  Slim chinos, like those by Mason’s (available at Barney’s New York and Douglas Fir), are also a great alternative.  In Milan, you will see men wearing navy chinos instead of jeans. 

Also, don’t be afraid to wear a blazer (roll up the sleeves to casualize it); again, just don’t wear a formal, structured blazer over a button down shirt and blue jeans.  The trend of the moment is a horizontally striped crewneck tee.  The gentleman in the gray jacket (right) has the right idea.