So, a big part of me nowadays is wearing nice clothes and looking good. I thought I'd post a little of what I've learned from my journey thus far. Looking good (to me, I mean) has really helped my self-esteem and maybe this will help someone out there.
First is pants or trousers. These are a major part of the wardrobe and they seem to get thrown to the side. First off, they can slim you or make you look horrible. To all men out there, if you have dress trousers, they are most likely made to be worn at the natural waist. The natural waist is where your side curves in. Usually it's right under or around your belly button. I know, most will say it's old man style, but it looks best and allows the pants to drape properly. Plus, if you have any belly at all, it will hide it and slim you down. You can wear a belt, but in my opinion braces/suspenders work best as they allow a nice drape. Nothing more classic!
Shirts are another issue. Figure out your correct neck size. If you cannot put two fingers (pointer and middle) inbetween your collar and neck comfortably, it is too tight. Slim fitting seems to work best for me, and I'm not super thin. It's not too baggy like traditional shirts and just look plain good. Start out with basic light colors and whites, along with stripes and such. The collars are not a huge deal, but pinpoint collars are the standard. Bigger men are often advised to stay away from spread collars as they can make a person look like they have barely any neck. But, if you are average sized, it's not to be worried about.
The shoes are important, but I won't stress it much. Black and brown go great with most things. Wear appropriate socks and, in my opinion, wear black when wearing black trousers.
Jackets (sport coats): The shoulders are the most important! When standing straight, your arms and sides should be essentially straight because of the shoulders. The shoulders should hug your natural shoulders and should make a nice V. If they are too tight or are going over your natural shoulder and not allowing you to move very well (there will always be some movement restriction, just note they are to enhance your shoulders, not be shoulder pads!) skip the suit. Make sure the jacket is long enough, it should end right at the upper thigh area. Measure at the biggest part of your chest, find that measurement. That is your jacket size. If it is a 40, for example, there is 40R (regular), 40S (short), and 40L (long). Find the correct length for you based on where the jacket lands. Also, if it is a sport coat, don't try matching pants as it most likely won't look like a suit but a badly mismatched pair of pants and jacket. I have successfully done this, though, with a black sport coat so it CAN be done.
Neckties. This is what I know most about. For starters, get basic patterns. Patterns work best with anything. Stripes work well, too, but I am not such a huge fan myself. Solids can work well, but can be bland. Basic patterns and florals are very nice, along with paisleys if you like that look. Match to your shirt. Generally ties are 3.5" in thickness, but skinny ties have been quite popular. Skinny ties are cool, but I prefer closer to average than anything. They also look way better on skinny people from what I've read online, so caveat emptor there. First things first, learn how to properly tie a tie. Learn the four-in-hand knot (YouTube has many great videos). This knot works for everything. You do not need to ever tie a huge Windsor knot even though most will say it's the most formal. The four-in-hand was the knot of choice for many years, and still is for a reason. Another great knot is the half-Windsor or Pratt/Shelby knot, if you prefer symmetry. Also, learn to make a dimple (essentially by making a crease while tightening the knot up your neck, YouTube has great videos). The tie should end at the waistline of your pants…no lower! Higher some people like, but that's an opinion not many share. Wearing under a vest allows for more mistakes (under a vest the tie and knot should be propped up a bit, too). Also, the smaller blade of the tie should be short than the fatter end, but if it isn't you can always tuck it into your shirt if the knot looks good or if the tie is quite long and you are a shorter male. If you are shorter (like I am) find ties by Ralph Lauren and even vintage ties as they tend to be shorter.
Pocket square/handkerchief: Not needed, but I like them. Learn basic folds by typing "how to fold a handkerchief" on YouTube. A basic white linen or cotton one will suffice for nearly any occasion but silk looks nice, too. Keep one handy for a special lady on dates if you're seeing a sad movie!
Hats. I don't know much about them. Just make sure it fits well and don't go too crazy with brim size. If it doesn't look good on you, find something that does!
I hope this helps someone. Of course, it's really all opinion and things I've read and learned along the way. If you like it, great 🙂 I know dressing up has really helped me feel better about myself.