Was simply going to address this over at Steve's place, but since he shut off the comments I'll spout my gibberish here.
First go read what Steve considers to be stylish with regards to formal wear. He's 99% correct but lives in Florida so there's always room for that one percentile of hickerish that follows everyone not from NY or London around.
I have several pairs of dress shoes and they are polished far beyond what can be achieved from patent leather. A good spitshine is deeper, glossier, and bespeaks a true understanding of proper footwear maintenance. Takes forever to get just the right shine this is true, but once the foundation hs been laid going back and spiffing them up is not a chore at all. And Cowboy boots are not stylish. Never were, never will be. One makes a statement by selecting the proper fabrics, style, aroma and accoutrements. One does not go shitkicker just because someone once said it's a way of being playful. There are dozens of things to do right, and each of these things can denote a certain degree of uniqueness, but being George Armstrong Custer for a day says you are happy with being half-dressed. This of course does not mean that men should not wear boots at formal affairs in Dallas. Well of course it does, but they wouldn't listen and it's because they wouldn't listen that makes it trashy. They do not revel in being sharp. They revel in being different because sharp takes too much time and effort.
Cummerbund and suspenders are proper formal attire, and there are many buns available that are designed to holster a small, formal weapon. But I've carried a large framed revolver when garbed in a monkey suit and it's all in the details. Owning one's own Tux is a must, and having it tailored specifically for you is really the only way to go. Leaving a little room here and there makes concealing your heat lots easier, and I've only been outted once by a particularly ravenous young thing who could not keep her hands to herself. Then asked if she could borrow my cell phone after mistaking my handgun for a dialy thingie that I wouldn't be caught dead with while formal.
When fitting into a 54 or 56 long, finding an off the rack tux can be daunting, especially when they expect your waistline to equal or exceed the girth of your chestline. But this is true for all men over the age of 35. We put on and take off weight seasonally and having that slightly oversized winter tux next to the form fitting summer one can mean all the difference in the world. I like parties of all kinds and never turn down the chance to play dress up so owning well-made suits has never been a big deal. Probably comes from wearing uniforms a lot. Try getting dress blues just right and you'll soon find that a tux is a piece of cake in comparison.
And yes, a pocket watch is a good idea. It's classy and who gives a shit if it doesn't get you laid because the object of your infatuation does not know this. YOU know it and that's what counts. And Steve is correct in saying that if a wristwatch must be worn then for the love of all that's good and just in the world go analog. Metal or obviously expensive leather bands only.
REAL studs, no plastic, thank you. Work on learning several variations of a genuine bow-tie knot. Get a small manicure set and do the frickin fingers even if it's just for this formal shindig. Like I said, you CAN wear your concealed carry weapon but NO spare magazines or Speed-Loaders. After you've been practicing for several decades a .32 Kel-Tec is just as deadly as a .44 magnum, so yes, by all means carry the smaller gun. Get a haircut at least two days before the event so it doesn't look like you've just gotten a haircut. Shave as close as possible without drawing blood. And just a touch of Aramis or Joop or Paco because women love the ever loving shit out of a man who smells good, but NO, repeat NO cologne with a picture of a ship on the bottle.
Black dress socks goes without saying. Trim the beard even trimmer than usual if you're a facial hair man. And now's the time to tell you a secret. Something that has NEVER failed me. Every, and I mean EVERY woman I have EVER known falls true to what appears to be an overly broad generalization. Girls who like beards give the best head. In every corner of the world. At any age or social structure. Drunk or sober. Rich or poor. Married or single. On the other hand, Girls who do not like beards just don't give average oral, they suck. I mean they don't suck. You know what I mean.
And I've left out a lot of other things but once you're headed in the right direction they come to you with time and patience and experience.
So dress right, stay in reasonable shape, and trim that thing. Dividends galore, lads, dividends galore.
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