1. Care for your skin properly! Well cared-for skin is always going to be easier to shave than dry, patchy skin. Irritated skin is going to be red and feel inflamed; unpleasant to experience and unpleasant to look at as well. Jack Black, Anthony Logistics, Lab Series, and Cosmedicine all make skin care for men. For less expensive brands, I know Target carries a line called Every Man Jack, and the products are of good quality. Moisturizer is key,
especially after you shave!
Any men's line is going to provide you with a product that has no odor or a faint masuline odor, as well as more masculine packaging so that if you're showering at the gym or at your girl's place and pull out your moisturizer, nobody's going to look twice.
For men's skin care, my top recommendation is
Kiehl's. Kiehl's is somewhere between high-end and Target, and they really have superior quality products. Nearly everything for men is odorless and the packaging ranges from nondescript (plain white plastic with black lettering) to masculine in appearance. I know that may sound stupid to say, but appearance of these products is a big deal to a lot of men.
2. Stop shaving with an electric razor. I know it's faster, but it does nothing to "train" your hairs to grow in one particular direction. It can even encourage your hairs to grow more chaotically.
3. When you do a wet shave, make sure it's really a wet shave. Don't just slap some gel-to-foam on your face and think you're doing a proper job. Wet your skin down with warm water before you apply any kind of soap or shaving cream. It helps if you shave after you shower (I believe most men do), but if you shower in the evening or something, just press a warm washcloth on your face for a couple of minutes before you get started.
4. Don't press so damn hard! If you have to press really hard to get a close shave, either your blade isn't sharp enough, your razor sucks, or your razor is a bad choice for the type of hair you have. Which leads directly to:
5. Choose a proper razor for your face. More blades does not always mean a better shave. Many men use razors with multiple blades, thinking that's the best choice. If you have a big problem with razor bumps and/or ingrown hairs, you might be shaving
too close for your skin and hair type, and you need to scale back a little bit. Try using a single blade razor, and use a new blade (or freshly sharpened blade) every day.
5. You can "train" your hairs, to a degree. Always shave in the same direction; don't switch it up thinking that's going to give you some kind of benefit. If you go with the grain, which I think it recommended, do that every single day. My brother used to go with the grain one day and against the grain the next, because someone told him it would reduce the appearance of the 5 o'clock shadow. It does not and his skin got fucked up. Consistency will encourage them to grow in the same direction.
6. Make sure you locate any ingrown hairs you can and gently pull them out of your skin before you shave. You can do this with a straight, sharp object like a pin or sewing needle. Now, don't dig around in your skin. Don't go tearing holes and poking things and drawing blood. You should be able to slide the pin under the portion of the hair that's above the skin and lift out the end that's grown back in.
Getting a good shave is harder for some than for others. Just bear in mind that just like with anything else, you get what you pay for. If you invest the time and effort into caring for your face properly, you will see results.