DorkDevil

1. Use a foundation, even if you cosplay a male character. It will look nicer if the entire face has the same skin tone and we are going to add the shadows anyway. Since my eyebrows are quite dark, I also use makeup to brighten them up a little bit.  If the foundation does not suffice to cover all skin blemishes you might use a concealer for that.

2. With some brown eyeshadow (darker than your foundation but not too dark either) we are going to change the appearance of the face's shape.

Warning: Don't use too much eyeshadow/paint/whatever, otherwise it will look fake. If something turns out not dark enough, you can always make it darker afterwards but if you mess up one step, you might have to redo all of them.  

First draw a smooth line under your cheekbone - make sure it's not too high.

Opening your mouth might help you to find the line to follow down to the level of your mouth, then.

Repeat on the other side and check if you're happy with the result. I suggest keeping it decent for now, since the stubble will reinforce that effect later anyway.

Add the shadow on your chin. Make sure to keep it visible, but rather narrow.

Follow your jawline to make your face look more angular. You don't really have to be very precise here.

(Optional) If you want you can add subtle shadows over the corners of your eyebrows too.

(Optional) Add the dark circles around the eyes, paying attention to the reference picture you are using. Not everyone's eye circles look the same and Dean's are large, albeit not too dark.

(Optional) With a small brush and still the same eyeshadow I usually add a dark line under my eyes, following my own eyes' wrinkles to make them stand out more, since Jensen Ackles practically is twice my age and I have not had the time to naturally copy all of his mature wonderfulness yet. Welp, hello makeup.

(Optional) If you are a perfectionist like me you can also add shadows on the sides of your nose (following your reference image(s)'s shadow-pattern) to make its shape resemble the original's. Carefully add the nasolabial folds. 

Smoothen everything up and add some last shadows.

Tip: I advise looking at your reference picture and deciding for yourself which shadows to add and which to leave out. If you add too many your face will look dirty, if you add the right amount the makeup will look convincing. 

3. Up to the next step. You'll need a roughly textured plastic sponge and dry aquacolor makeup - which basically is the kind of makeup usually used with a wet sponge to paint the faces of children and clowns. And ours. But not with a wet sponge. I. Uh... You get what I mean. (You should be able to find these things in carnival stores and costume shops. I partially work at an old-fashioned toy store, that's where I got it from.)

Dip the sponge into the dry color and then carefully tap it all the way from your 'sideburns' down to your chin. Again, just follow your reference image's pattern for that, since everyone wears their stubble differently and idk. Just do it. The plastic sponge will leave an awfully realistic stubble if you do it right.  Don't scrub the sponge over your face, use wet color or smear over it. It will look ugly and you don't want that. Stick to the rules and don't be a Loki.

Don't forget your upper throat. It wants stubble too.

Moust-ubble. 

4. Done with the hair and basically everything else. (You might want to wipe your hands after that.) Just add some powder for the highlights - upper cheeks, forehead and the back of your nose.

(Optional) If you are really crazy and/or devoted (and Castiel knows I am), you can use natural-looking/pinkish lipstick to draw the lines of your lips anew, in order to make them look like the original's.

Don't forget to powder them after that though. We don't want any gay Deans running around. (Or do we?)

5. That's almost it. Onto your head the wig goes (unless you are using your own hair).

6. Adjust hair and face.

7. Remember that you haven't dressed up yet.

8. Get dressed and wink.

9. ???

10. Success.

You really should get dressed before doing all that though.  And don't worry if it doesn't turn out right immediately, it'll get easier and quicker the more you practice. 

Also: If you’re planning on making gifs, learning the character’s facial expressions is very helpful!

I hope this will make crossplaying a little easier for you guys. Feel free to contact me if any questions remain. Good luck!