Of course, a great looking pompadour starts with a great cut. You may have a bit of trouble finding a barber who can do one well, so call around and ask. The hair is clipped very short on the sides and back (I love to take them nearly skin tight on the sides and back, so there's a nice contrast with the long top). The top is left with considerable length—the amount of length on top is really a personal preference, but you should plan on having four or five inches to get the pompadour just right. Often, if the top is left very long, there will be minimal blending with the sides. If combed straight down, the style would resemble a bit of a bowl cut, but the line will go away once the hair is slicked back.
To get a good pomp going, you'll need the right products and tools. First, you'll need a great pomade (for finer hair, go with a lighter pomade like Woody's Pomade ($16), and for very thick hair, you can't beat Murray's Pomade ($12)). One note of caution, if you use Murray's, your hair won't fall out of place, but it will take several shampoos to get the stuff out. You'll also need a blowdryer and a good brush (We love the Denman Classic Styling ($20)). Optionally, you may also want to have a great hairspray on hand, such as the Keratin Complex Firm Hold Hairspray ($26), to lock the style in place.
After a shower, towel dry your hair. Next, using your brush and blow dryer (high heat, low air flow), dry the hair on top by directing the front up and back. You may not need to use a blow dryer, but the heat will help give you more height and set the style up.
Once the hair is dry, apply about a pea-sized amount of pomade to the palm of your hand and work your hands around a bit to warm it up and emulsify it. Don't use too much as it will weigh your hair down—you can always add more later. Smooth the product through the hair until it is evenly distributed. Now, take your brush and slick the hair straight back on the sides and back and towards the center on top. If the hair isn't slicking back, you can add more pomade. At this point, you've got a decision to make. Part or no part? For a pompadour, either works, but we prefer unparted pomps.
Now for a little fine-tuning. Take the hand not holding the comb and place it on top of your head right in the middle so your entire hand comes in contact with the slicked back hair. Carefully push this hand forward while brushing the hair in front straight up. What this is going to do is help you get more height and volume at the front. This is probably going to take a bit of practice but keep at it. Once you've got some height on the front (viewed from the side, your hair should form a ramp from the crown to the front), you can now brush the hair near the top on the sides straight back. You can also use a comb to very lightly direct any hairs which may be out of place back to where they need to be. Once everything is in place, you may want to set the hair with a light coating of hairspray.
The pompadour isn't for everyone, but if you've got the hair and face for it, the style will certainly set you apart. If you want to see some very cool pompadours, check out the website for the Dutch barbershop site Schorem Haarsnijder en Barbier (hint: Google Chrome will translate this site for you). Now, run down and get a sleeve of tattoos and join a Rockabilly band or grow a beard and go adopt the hipster look. You're ready to rock the Pompadour.