First. What is your personal brand? What are five words that describe you? Ask your friends for a few words to describe you. That is your current style. If that doesn’t work for you, what do you want instead? List those words.
How conventional are you? Do you take risks? Are you serious? Playful? My personal brand has a lot of humor, and I am pretty comfortable being the center of attention, so I can get away with wearing a bright pink sport coat, or four different patterns (coordinated, of course), but I fade into the woodwork if I’m wearing a grey suit, white shirt and red tie. That’s me. Who are you?
Look for other styles
Next, find magazines that speak to your style. Look at the ads and the photos. What are the guys wearing? Imagine yourself in that. Would that look good on you? (some of the things in magazines are to be avoided, by the way) Read the style articles, too, but don’t always believe them when they say that this or that trend is coming back. “Hats” have been coming back for almost 50 years, but have never quite recovered since the 1950s. Don’t buy one because they are trendy, buy one because you like it.
Go to a store (that fits your style…) and browse. I know, we’re guys, we prefer hunting over gathering. So, think of this as scouting for your prey. Take a friend whose judgment you trust and run ideas by him / her, but make your own decisions! (BTW, you will make mistakes. That’s OK, that’s how you learn…) If you don’t have a friend you trust with this stuff, walk up to someone else in the store and ask his or her opinion about the shirt / suit / shoes you are wearing. This is a fun way to meet people, too.
Get some professional help
Find a knowledgeable salesperson in the store and enlist his / her help. Remember, they may be on commission, so they may want to sell you stuff you don’t really want, you will need to use judgment here too. A good salesperson won’t do this, preferring to build a relationship instead. You want that too, so that they will tell you about upcoming sales and offer to put stuff aside for you. This is VERY important if you are in any way a non-standard size (says the guy who is 6’5″). Anyway…ask him / her what colors and cuts look best on you. Not everyone looks good in all colors and patterns. Blue is great for me, dark grey not so much. Similarly, bold patterns make people look bigger and broader, which is great if you are 5’6″ and 120 pounds, but not if you are 6’0″ and 350 pounds.
Lastly, enjoy the process. There is a science, as well as an art, and you can learn both. Don’t take it seriously (except for those few occasions when you must, like funerals).
By the way, that is me in the photo above, no stock photo could capture the mood quite right….