The one-time olive jar in which I keep my (too large) collection of silk pocket squares atop my dresser.
One easy way for you to kick your personal style a notch or two is by adding a few silk and/or wool pocket squares to your wardrobe. Typically, these measure 10"-16" square, or slightly larger, and the better ones have plump, hand-rolled edges. You'll know it when you see it. Keep your eyes open while visiting your local thrift or consignments shops. You stand a good chance of coming across a few cast off pocket squares from Italy, Great Britain, China, or Japan, or that still have lots of life left in them.
And no. You don't need near as many as shown above. Five or six in various patterns (paisleys, polka dots, foulards, stripes, etc.) ought to do it. Even with, say, just a navy blazer and a sports jacket or two in your closet, you can change up your overall appearance each day without repeating one "look" too often. Pocket squares never look exactly the same once they have been stuffed into the outter chest pocket of your jacket. There is always a slightly different variation on what pokes subtly out of your jacket or blazer pocket.
Keep in mind though that you never want to match your pocket square chosen for the day too closely to your necktie if you wear one. Why risk looking like you've purchased a matching set (cringe!) at the Men's Warehouse, Kohl's, or T.J. Maxx? It's far better to throw caution to the wind, demonstrating imagination and sartorial vision. Don't worry. It's hard to go wrong here. Either pick a square that has nothing to do whatsoever with your tie, which is perfectly acceptable, or choose one that somehow compliments your tie in some way, picking out one of its colors for instance. Maybe the necktie you've put on is a navy and yellow repp stripe, so try choosing a square that's got a bit of navy, or a bit of yellow in its designs.
And what about wearing the pocket square? Well, there are all kinds of complicated folds that you can find and try thanks to the internet, but I suggest simply stuffing your pocket squares into your jacket pocket and leave it at that. Far better to appear slightly nonchalant than overly self-conscious about your clothes and accessories. What you are after is a pulled together, yet relaxed appearance that somehow does not look as though you've spent hours planning everything the night before. That is the elusive sprezzatura (a popular Italian word right now) that seems to be discussed so much in the menswear blogosphere these days.
One thing. I'd suggest exercising a bit or restraint here. Just let a bit of your square show in your jacket pocket. No sense in going too over-the-top at this stage of the game in your sartorial journey from sweats, sneakers, and backwards baseball cap to a pulled together, classic appearance. Better to keep things understated and comfortable than risk looking like a cartoonish dandy from a Gilbert and Sullivan musical.
Returning to the matter at hand, consider your attire and manner of dressing like an adult male to be an ongoing work in progress that you'll nail some days and not quite on others. The fun comes in trying. And most of the time, you'll look miles better than most other men on the street in most places these days. So, really, don't obsess too much about getting it exactly right. Have fun getting dressed in the morning, relax (you look great), and go forth!