My friend and I were arguing about whether or not one should button down the collar of a shirt if he was not wearing a tie. I said no; he said yes. Does it matter? If so, what is the ruling?

Don’t go patting yourself on the back just yet; you’re both wrong. In your quite needless debate on buttoning shirt collars, you both overlooked one very obvious point: Button-down collars are ugly. In this fashion-forward day and age, nobody should really be wearing a collar he can fasten to his shirt when there a plethora of fantastically stylish collar types to choose from instead. From narrow spreads to wide spreads, the collar width and size is a great way to add detail to a regular dress shirt in a way that the stifling structure of a button-down collar can’t.

Formal vs. black tie

I recently got an invitation for a Saturday night affair that said “formal” dress. I told the host that I thought it meant a tux, but he said no, just a suit and tie. That doesn’t seem right to me, and I told him most guests would agree with me that formal means a black tie and tux. Who is right? I don’t want to be the only one there NOT wearing a tux!

I would listen to your host if I were you. You seem to be making the common mistake many men make with the term “formal attire;” you’re confusing it with “black tie.” A black-tie event is one in which you would wear a tuxedo; whereas formal attire requires you to wear a suit and tie -- think cocktail-appropriate attire.

For a Saturday night event, either style of dress is appropriate, so you simply have to follow the directions given to you by your host. Trust me: You won’t be the only one there not wearing a tux. And if you are, it means that you’re style-savvy enough to know what “formal” means. You take the lead from the host as to which style of dress is appropriate, so as soon as those tux-wearers see how you and your host managed to show up in fabulously dapper suits, they’ll feel over-dressed and out of place.

Shoes and socks

Wearing the right socks has always been my weakest point. I have always worn white socks to work. My problem is that I have all different kinds of shoes. What socks can I wear with my Converse sneakers and my white leather loafers?

I am dedicated to helping you with your sock problem, but first and foremost I pray that these two shoe styles are not the only two you own. That being said, on to your sock color dilemma...

For your laidback Converse sneakers, I would stick with thin, white, ankle-length socks if you’re wearing them with shorts. If they’re being sported with jeans, opt for a light or charcoal-gray sock. (As an aside: The gray sock is severely overlooked, as many people tend to think that they should only be choosing between a black or white pair. When it comes to wearing jeans, gray socks are a subtle way to coordinate with both the shoe and the jean color). My rule of thumb is to avoid wearing white socks with jeans at all costs; they tend to stand out like a sore thumb.

As for your white loafers, since you are presumably only wearing these shoes in the summer months (and if you’re not, immediately slip them off your feet and put them at the back of your closet until the end of May), it is perfectly acceptable to go sockless. In fact, I recommend that you go sockless with white loafers. And, by the way, only wear them with jeans; paired with anything else, they’ll look rather “nerdish.”