Sneakers with Suit – This should never be an option, I don’t care what your profession is; rock star, actor, hipster, etc. This is not a good look. PERIOD. If you put on a suit, there is a good reason for it. If you don’t wear it for work and it is something of a rarity for you, then you must be wearing it for something formal. Putting on sneakers with a suit diminishes the importance of the event you are attending and makes you look like an apathetic asshole.
Shirt buttoned to the top with no tie - Odds are you are not going to a Prada ad shoot, so cut the shit about wearing your button down shirt and buttoning it up all the way to the top whilst avoiding to put on your tie. I don’t understand why anyone would find this acceptable, it looks downright silly.
Square toe shoes - I mean, there is not much to say about this. Just don’t do it. For fuck sake, look how UGLY they are. Please, if you own a pair of these, just go and burn them or donate them to a third world country where owning a pair of shoes is a luxury.
The illustration below gives you some further edification.
Matching your pocket square to your tie – Do you want to look like a fucking groomsman/poorly dressed groom? If the answer is YES, then please, by all means, match your pocket square and tie. I understand why some people might opt for this (i.e. lazy men). It is easy to pick up that cheesy shirt/tie/pocket square combo that was put together by some brand in the department store as you walk by it. Do yourself a favor and KEEP WALKING. When in doubt, use a basic white pocket square as it will go with ANY shirt and tie combination you throw on. If you want to add some flair to your outfit that day, do it with your socks, a well placed lapel button or tie bar.
If you ever bought a combination like the above tie/pocket square, it’s OK, just don’t ever wear them together.
Athletic socks with dress shoes - This has to be one of my biggest pet peeves. There is no excuse for something like this to occur…EVER…it is ugly and inexcusable. If a woman ever looked down at your feet to find this atrocity, I GUARANTEE you she will walk away. The type of woman a gentleman will want is particular and she will not tolerate this level of ineptitude.
I will call you out on this if I ever see it.