Dear Colin: I've been told that if I don't wear "proper clothes", there will be "CONSEQUENCES". You're a fashionable chap, any pointers?-ADAM
Send, “Dear [Name]….” and a question for the advice of my muse!
“First of all, please keep in mind that whoever told you that only had your best interests at heart.”
“I’ve been forwarded photos of your wardrobe (and wardrobe malfunctions) and I believe I may be able to save you yet. We’ll start with small, easy steps and not sweat the details. First, what you’re going to want is a Shirt. This part is non-negotiable. Pick one or several in a single, solid color for starters. Patterned shirts are Advanced Mode, at your current state you are not ready for that kind of responsibility. The safest option is white, but light blue, light purple, cream and dark red are also good choices. When in doubt, show the color to Pierce or Shaundi and listen to them.”
“Next, you’ll want some nice pants and a suit jacket to pair with the shirt. Again, start off with something safe first or you can go horribly wrong if you don’t know what you are doing. A dark gray, dark blue or dark purple can work well, and black is always in, but looks the most formal. Make sure the pants and the jacket match, I cannot stress this enough!”
“Now the tie. In a more casual setting this can be optional, but more formal settings require a tie. Picking the right tie can be the hardest step for the, ahem, fashion challenged. It is a skill that develops with experience. To help you out on your first time, show off the potential tie along with the rest of the outfit to someone and pay close attention to their reaction. Some negative warning signs to watch out for are the following: bulging eyes, wrinkled nose, gasps of shock and revulsion, color draining from the face, retching noises and more. Positive signs are nodding, hums of approval, smiles of the mouth and eyes, and encouraging words such as ‘that looks good’ or ‘finally, something decent’. Again, when in doubt, bring along Pierce and/or Shaundi or show to the staff at the store. As a last resort, you may message me.”
“The final step is picking the shoes because oh god, mate, you’re seriously not planning on wearing those combat boots with your nice suit, are you? No, don’t answer that, and no, going barefoot is also not acceptable. There are tens of varieties of mens shoes and fashion rules of what goes best with what, but that is beyond this basic guide, so all I’m going to say is pick something that’s dark, leather, looks polished and has a fairly flat sole with a little bit of heel. No boots unless it’s winter and/or you’re wearing jeans, and since you’ve approached me for pointers on ‘proper clothes‘, you’ll notice I haven’t included jeans. Don’t wear jeans with a suit unless you really, really know what you’re doing, and trust me, mate, you don’t.”
“I suggest you print out this guide and take it with you to the store to reference as needed. Good luck and congratulations on your first steps toward looking like a fashionable member of society. Best regards, Colin.”