Dec 13

Choosing A Proper Wig

We are fortunate to have Carollyn Olson and Kathy Hamilton help us in choosing a proper wig.

different wig styles

When a man goes out to buy his first feminine wig, it can be scary, intimidating and unnatural. I know from experience because I’ve been there and done that.

When I seriously started cross-dressing, about 20 years ago, I had been wearing, for the longest time, a wig I purchased at a garage sale. It looked good, but it was old and hard to care for and it wasn’t me. If I wanted to grow as a woman, I decided I had to do something about my hair. So, I bit the bullet.

My first move was to phone a local wig salon and ask if the staff was comfortable with a cross dressing client. On my first call, the lady responded “Yes, by all means.” I was thrilled, but going to the salon would be even harder to do than make a phone call.  The lady at the other end of the call would never know who I was after I hung up the phone. It would all change when I walked through the salon door. I made an appointment for the next week.

The days couldn’t go fast enough. When the big day finally came, I went to the salon in male mode, with my wig in a plastic bag. The stylist, Linda, was fantastic. She greeted me at the front counter (luckily the salon was empty at the time) and guided me to a private room.  I showed her a few current pictures and she was impressed, but agreed with me the wig had to go. I had an idea of various wigs I would like to try, but she handed me a wig book and said “see what you like.”

In the meanwhile, Linda put my wig on my head and began to style it the best she could. About 10 minutes later, the wig was much different, fuller and more lady-like than I could have ever expected. But, I was still in male mode and it was hard to see the true results.

We made an appointment for me to return a week later, but this time as Carollyn. She kept my wig for cleaning and styling and gave me a similar “loaner” wig to wear when I returned.

Carollyn Olson in first new wigThe big day came and dressed in a red sweater, black skirt and heels, I entered the store. Linda, who has become a dear friend, was waiting for me and again we entered the private room. She gave me a number of compliments about my appearance which helped me relax. Once in the chair, she replaced the substitute wig with my original wig. I looked so different and was pleased with my new look, but she wasn’t done yet.

Linda asked me if I would like to try a couple of other wigs. Of course, I said “Yes.”  Linda had been thinking about my hair for a week and had a few ideas. She left the room and returned with a handful of wigs, in all different styles and lengths, many of which I had selected during my earlier visit.

Linda explained that I have an oval face and light (Norwegian) complexion, thus, certain styles, including a long frock, would not work for me. So, we aimed for a shorter style wig, no longer than top-of-the-shoulder length with a golden blonde or frosted/rooted color, probably with bangs, due to my high forehead. (Please see accompanying facial chart with this article).

After trying four or five wigs, none of which produced the result I was looking for or that weren’t “really me,” her associate entered the room.

“Linda and I have been talking and we think we have something you will really like,” said Cindy. “Close your eyes and don’t open them until I tell you to.”

I complied and within minutes I was 15 years younger, with a new look, the same hair style I currently wear – Noriko Sky Sandlewood. I immediately gave my old wig to the salon to donate to a cancer charity and handed Linda my credit card.


Carollyn Olson in Norika wig

My first purchase was $165, but it was more than worth it, and one of the most satisfying days of my life.

Now, not everyone will be as fortunate as I was, or can afford such a high-priced wig, but consider the following factors.

  • Budget
  • Function
  • Shape of face
  • Own skin and hair coloring

Budget — While there are high end human hair wigs costing hundreds and even thousands of dollars it is quite possible to find very good quality synthetic hair wigs for a fraction of the cost. There are many varieties of wig companies offering varied levels of pricing at $100 or under on the internet. My favorite company on the internet is Name Brand Wigs due to its selection and styles, but there are many other companies on the internet that might suit your style, fancy or pocketbook. Salons have a number of other wig products, but they are usually higher than a similar wig on the internet. One problem, though, many hair dressers will not trim or style a wig that is not purchased directly from their salon. Try to stay away from the cheaper and lower grade wigs such as Paula Young (even though I have friends who love Paula Young wigs) and similar products available on the Home Shopping Club and QVC.

Function — Decide on the everyday use of the wig. Is it for attending a formal workplace, a glamorous party or simply for wearing in the comfort of your own home? Such considerations will impact on your choice of wig style and color. For example, if attending a party you can obviously be more fashion conscious and daring with color than if you are simply trying to achieve a subtle everyday look.

Color — If trying to match your own hair color, clip a small sample of your own hair to compare with on line color swatches. Your complexion color will have a lot to do with your hair color choice. Compatibility is important. You want your hair to blend in with your complexion and not the opposite. As you would with clothing, compare, contrast and then decide what looks best for you.

Facial Shape –Always choose a wig that enhances your natural facial shape and bone structure. Most common facial shapes are oval (longer length than facial width but extremely well-proportioned), round, narrow-faced or square-faced where there is a prominent jaw and brow/forehead of similar width. Any length and style of wig compliments the perfect oval-shaped face if you are fortunate enough to have such facial features. Rounder facial features and strong brows and jaw features normally require longer styles and the addition of layers or curls help to diffuse those strong facial characteristics. Try to incorporate good bang length to eliminate prominent brows in particular; page boy styles are particularly successful.

face shapes

Your skin tone, your natural coloring, plus, importantly, the shape of your face all are factors to be considered. You don’t need this book to tell you that men’s faces are quite different than women’s, and whilst there are 6/7 recognized different types of faces, many men tend to have only 2/3 of these, mainly square or oblong faces (see more below).

But, as a starter, well before choosing a wig style, do the following to work out what type of face you have, measure:

  • Your face across the top of your cheekbones
  • Across your jaw line from the widest point to the widest point
  • Across your forehead at the widest point (usually somewhere about halfway between your hairline and eyebrows)
  • From the tip of your hairline to the bottom of your chin

measuring face shape

With the following information you can determine which face is the most similar to yours, and which wig style you should consider to purchase, plus more importantly, which wig you should avoid.


square face shape

Square shaped faces are as about as wide as they are long, and have a strong, square jaw line and usually an equally square hairline.

Look for wig styles that add height to the top of your head, as this will elongate the symmetrical square shape, and narrowness at the sides. Off-center parts with height at the crown look great on square shaped faces and short-to-medium length wigs, especially with waves or roundness around the face to soften the angular shape, are also good choices. Wearing a wig with layers and wispy looks around the face is another way to soften your face shape and will achieve a nice balance to your otherwise straight features.

However, avoid long straight styles that accentuate a square jawbone, straight fringes or center partings, or a straight bob ending at the jaw line.


Oblong face shapeOblong faces are longer than they are wide and are often long and slender, about the same width at forehead and just below cheekbones. May people with oblong faces have a very narrow chin or high forehead.

The wig style you choose should add width to your face to help minimize its vertical length. Preferred wig styles are short to medium in length, with longer top layers such as wedges and graduated bob cuts. Those wigs with chin and shoulder length that turn under or flutter out also work very well.

Layered styles in medium and longer lengths, with wavy and curly textures, will flatter the face and neck, whilst obscuring the straight long lines of an oblong face; in addition, straight across bangs, feathered bangs, or half bangs with side parts soften the forehead.

Long haired wigs should be avoided as they will make your face appear even longer 


diamond face shapeThe Diamond shaped face is widest at the cheek bones; with a narrow forehead and jaw line each of approximately equal width — in some ways a cross between heart and a dramatic oval shape!

Fortunately for those with this shaped face, it allows for a number of hairstyle options. Ideally, though, diamond shaped faces need a wig styled with fullness or width in the forehead hairline and to the lower cheekbones of the face. Hair should be styled close to the head at the upper cheekbones where the face is broadest. Wig styles that tuck in behind the ears also will work well, especially if you have a good cheek bone structure.

Almost all hairstyles work with a diamond shaped face, so you should experiment. If you have a dramatic diamond shape, leave weight in the back nape area and this will achieve a balance between your cheekbones and relatively delicate chin line.

Wearing a wig with height on top or volume on the sides is to be avoided. Whilst some fringe cover can hide a narrow forehead try not to wear too much hair on your face, thereby hiding your best features.


heart face shapePeople with a heart shaped face have a large and wide forehead, high cheek bones, sometimes a widow’s peak hairline, and a narrow “v-shaped” chin. Look for a wig that allows you to bring some hair across your face to soften its width. In addition, keep the hairstyle closer to the head near the eyes and fuller around the jaw.

Where additional width is desired, this can be done below and in front of the earlobes. Longer, layered hairstyles work well and a chin length bob is ideal for this type of face shape as it makes the jaw area appear wider and more balanced.

Styles with too much height at the crown should be avoided otherwise the face will look longer.


oval face shapeWith an oval shaped face the length is, typically, equal to one-and-a-half times the width is slightly narrower at the jaw line than at the temples, and the hairline is often gently rounded.

This type of face is well proportioned and allows for the most versatility in wig choices and, in fact, most wig styles whether short or long, straight or wavy are suitable.

Consider your best features such as your eyes, cheeks, or mouth and then accentuate them with your wig style.

Styles that cover up your “perfect” features such as heavy fringes, or too forward-directed styles should be avoided.


round face shapeThe round shaped face is as wide as it is long, and full-looking with a round chin and hairline; the widest part of the face is through the cheekbones. Good choices are wigs with a fullness and height at the crown, but not at the ears; off-center partings help reduce the face’s roundness. Wigs with a short, swept-back hair style or with a style longer than chin length should be considered.

To help make your round face shape appear longer and narrower, aim for wigs which have layering at the top to achieve fullness, whilst keeping the rest of the cut relatively close to the face to elongate the round face shape.

It’s best to avoid chin length hair and center partings as these tend to accentuate roundness. Because the widest part of your face is at the cheeks and ears, you need to avoid having the fullness of the cut there, as it will make your face appear wider. Short crops or straight “chopped” fringes should also be avoided.


pear face shapeThe cheekbones and jaw line of a pear shaped essentially broaden to showcase a wider faced look, and the face features a distinctly narrow forehead, with a rounded chin. It’s best to look for wigs that will add volume above the jaw line as layers can create fullness on the upper half of the face.

Hair on the sides of your head and at the nape are best set and combed in a pattern close to the head since any style too voluminous will add weight to the bottom of the face. However, don’t be afraid to show your forehead as this will draw attention upward and away from the jaw line. Also, if you have bangs, angle them slightly and tuck them behind the ears to draw attention upward.

It’s relatively easy to work out which shaped face you have and which wig will suit you the best; if you can’t do this yourself ask a friend for help — or, failing that, try and get advice from a qualified wig vendor or other beauty practitioner. In any event, getting the right style is essential and will lead to you having that much more confidence in getting out and about.

More information on face shapes here

Don’t be afraid to ask a stylist for help. Remember, our money is just as good as the money of any other woman.

Lucille Sorella gives us some of the mistakes to avoid in choosing your wig

A complete guide on the history of wigs and everything you want to know about wigs is in the Sister House Wig Nook

Carollyn Olson