To be honest, fashion is not something you can go digging around in 1996 to find out about, it is very much a whim of the season. However, when it comes to being 'dressier,' there is a great deal that has not change. Now, there is a large emphasis on a more classic feel with better fitting clothes, a far cry from the '80s shoulder pad craze.
Basically, if you're looking to bump up your style a bit:
- Beards are perfectly acceptable if you keep them neat. I would rather see a beard on someone than razor burn that would make me have PTSD.
- FITTING CLOTHING should be the single most important part of any man's clothing. If you're wearing baggy clothes to hide weight, lose it. You don't have to wear a twelve year old's shirt, but the fit of a garment is important.
- Dark wash jeans, they are extremely versatile and go well in the summer and winter.
- This is a preference of mine, but a brown banded and black banded leather watch. Steel watches are fine if you're a diver in my opinion, but you see them everywhere on any person who has a watch. Watches should also be simple, sleek, elegant. They are meant to tell time, not wind speed.
- In terms of suit style, a black suit should be a staple for every man. It goes with every occasional from weddings to funerals. Black suit with white shirt and black tie is a classic combination that seemingly few people go to. Try pairing a black tie with another color shirt like pink, French blue, or even a Gingham shirt and you'll find some great options. Darker brown and gray are also good choices, but have a little less utility.
- The shoulders should fit ON YOUR SHOULDERS and should not protrude beyond them. The sleeve length should be tailored so that 1/4 inch to 1/2 of cuff shows when your arm is at rest, regardless of if you're wearing French cuff or not.
- In terms of size around the midsection, you should be able to fit no more than your fist between your torso and the back of the buttons. Anything more than that, regardless of your weight, is too much.
- Buttons on suits: A two-button is a go-to choice now. Three buttons often look too boxy, they come off as pretentious. There is a time and place for them, but just like light khaki suits you need to be a particular build and look for them. They go 'sometimes-always-never' meaning the top button is optional, the middle is not, the bottom should never be buttoned. On a two button, it goes sometimes, never.
- Pleats in male dress pants are typically a bad choice, opt for a pair of flat-fronts and it will quickly enhance your dress.
- In terms of length, they should not bunch all at your feet, they should 'break' once and then terminate.
- BURN YOUR BLACK DRESS SHIRTS AND DO NOT PAIR WITH A WHITE TIE. This is not, nor will it be again, your prom in 1998. Darker shirts are fine when paired with an appropriate tie, but a black dress shirt is tacky. As are white suits. You aren't God or Satan, no need to dress like it.
- Your shoes should follow your sock color, not your suit. If you have a navy suit and are wearing black socks, black shoes it is. If you are wearing brown socks, brown shoes it is. Your coordination for belt, shoes and socks should all be the same color. Socks can be in a slightly different color but same palette.
- Learn how to tie and dimple a necktie properly. Learn the four main ways to tie one if you want to add a bit more arrangement to yourself. Your tie should be no more than 2.5 inches wide, about 2 inches is optimal.
- Silver based items (watches, cuff links, tie bars) are universal. It takes a particular person to pull of gold.
- Cuff links, tie bars, and pocket squares can all be great, stand-out accents. However, you should pick between one of the three and none should be obtrusive.
Look at Cary Grant, Steve McQueen, and Jimmy Stewart for some stalwart standouts of past style. George Clooney, among others, is a person now who exudes this sort of traditional style in a new way.
I'll add more later.