I have written a great deal over the years about getting your colors right from the start or as soon as you can to avoid wasting money. You can accomplish that by going to someone like Amy at Just You in Las Vegas because she has been in the business for so long and made up so many men just like you. Even if you were lucky enough to have purchased a wig in your natural color you are off to a good start but that part is easy. Getting foundation, lipstick, eyeshadow, blush and highlighter correct is an art and it takes an artist to get it right.
The same logic is applicable for wigs because there is a difference between what you like and what you look good in. The style worn by the hot chick in high school may have worked for her but not you. There is a chicken or the egg dilemma here for some as to do I buy the wig first or get the makeover first? I recommend going to a wig pro wearing your makeup which helps them find the correct color and style that compliments your face. It needs to be noted here though that older crossdressers must consider their current hair color. What was brown years ago is gray and white now and the skin lighter. The gallery below is my attempt to demonstrate how your look changes when you change hair colors. I took the original picture below and only changed the hair color, nothing else. The fourth frame in the gallery (MEDIUM BROWN GREY) is the original.
The 1st picture in each row is the lighter color which gets darker as you move right for each shade. If you think that the skin tone changes as the shades get darker you are wrong I only changed the hair color, everything else is unchanged. If this experiment works you will think the lighter colors make me look softer in the face while the darker colors bring out more detail and detail. At the very least you will note the contrast between the hair and face from frame #1 ASH BLONDE to frame #6 MIDNIGHT BLACK.
It is also important to note that because the only thing that I changed was the hair in each example the makeup was done for Frame # 4’s brown grey look. The foundation, contouring, and eyebrow pencil would need to be changed to compliment the different wig shades. The lipstick and eyeshadow eyeshadow have more room to play.
Because my eyes are blue I would choose reddish brown to medium red lipstick and copper/ bronze or brown eyeshadow and medium brown brow pencil on the first row.
Medium red lipstick shades and brown to dark gray or black eyeshadow and gray to black eyebrow pencil on the second row .
Medium reds, brown or bronze lipstick shades with brown or maybe bronze eyeshadow. I would also change to a warmer foundation shade with more of a bronze contour shade and reddish brown to dark brown eyebrow pencil for the 3rd and 4th rows.
After many years of trial and error I have settled on the medium length page/bob style wig which is very easy to style right out of the box. I have also limited my colors to blondes, and light browns both mixed with gray tones for s softer look. I am also toying with a salt and pepper grey wig in this style but my ego has not agreed so far.