Your Crowning Glory Revisited

Reader comments to my Your Crowning Glory post moved me to write this addendum to that post.

Large Caps

Many of you are big girls with big heads (myself included). Big heads call for big wigs (large cap size wigs). 

Some average cap size wigs can be stretched to fit our big heads, but the fit can be tight, so tight that they pop off your head. They also can leave welts on your forehead and even cause headaches (been there, done that).

Large cap size wigs are the solution. The problem is that there is a limited number of large cap styles. I searched the Internet and turned up a wig seller with 74 large cap styles (click here to see the 74). There may be a few more, but my guess is that 74 is close to the maximum number of available large cap styles.

Personally, I have large cap wigs from Envy, Noriko and Raquel Welch and I am a satisfied customer.

Roots

I love wigs with dark roots. 

For more authenticity, buy a wig with dark roots. The average person will be fooled thinking no one would wear a wig with visible dark roots – it’s counter-intuitive. So dark roots “prove” that your wig is the real thing.

I lost count how many times I have received compliments about my dark root hair. Even when I was doing outreach with an audience that was aware that I was a man in a dress, I received comments indicating that the commenters thought my wig was the real thing. 

Dark roots make a difference and definitely increase your passibility.

Wearing Boston Proper

Frank Marino, professional femulator

Your Crowning Glory

Choosing and wearing a wig is one of the most transformative (and sometimes intimidating) steps in crossdressing. The right wig can help you feel confident, feminine and expressive—but the wrong one can feel uncomfortable, look unnatural or just not suit your face or style.

Here’s a practical guide of wig tips for crossdressers, whether you are just starting out or looking to level up your femme presentation.

Know Your Goals

Do you want to pass/blend or are you going for dramatic flair?

Will you be wearing the wig for everyday use, photos or just for fun at home?

Are you going out in public or staying private?

Your answers will shape everything—from length and color to cap style and price range.

Choose a Color That Flatters You

First-time tip: Stick close to your natural hair color or a shade or two off (lighter or darker). This will feel less jarring and helps you adjust.

Skin tone matters:

Warm undertones? Go for golden blondes, auburns or chestnut browns.

Cool undertones? Ash blondes, black or espresso shades pop.

Avoid ultra-fake colors (like neon pink) unless you’re doing cosplay or drag.

Pick the Right Style for Your Face Shape

Round face? Go for longer styles with layers or waves. Avoid short bobs that emphasize width.

Square face? Try soft curls or side-swept bangs to soften jawlines.

Long face? Choose styles with volume at the sides or bangs to visually shorten the face.

Oval face? Lucky girl! You can wear any style.

Short wigs can be cute and manageable—but many crossdressers find medium-length to shoulder-length styles more feminine and flattering. However, a long style on a mature lady is unusual and may out yourself as a crossdresser. 

Cap Construction

There are three main types of wig caps:

Basic cap (wefted): Affordable, good for beginners, but less realistic.

Lace front: Natural-looking hairline, great for off-the-face styles.

Monofilament or hand-tied: The most realistic and breathable—but also pricier. If you are out among the civilians, you want your wig to look authentic, which means purchasing a more expensive wig. That’s what I do and on more than one occasion, a civilian thought my wig was my real hair even when they knew I was a “man in a dress”!

Pro tip: If you’ll wear the wig for hours, ventilation and breathability matter.

Secure It Right

To prevent slippage, use a wig cap to flatten your hair and keep things in place. Try wig grips (like velvet headbands) or double-sided wig tape. If needed, bobby pins or wig combs can give extra hold—especially on lace fronts.

If you have a full head of hair, braid or flatten it beneath the cap. If you’re bald or shaved, use a wig grip if you must (I am balding, use nothing and have seldom experienced slippage).

Style It Like You Mean It

Comb with a wide-tooth comb (never a brush) for synthetic wigs. Add a little dry shampoo to reduce fake shine on cheaper wigs. 

Don't use a generic hair spray on a synthetic wig; use a wig hair spray instead. Use heat tools only on heat-resistant synthetics or human hair wigs.

Consider thinning or trimming bangs slightly if they’re too long—carefully!

Want extra flair? Add a scarf, headband, or beret for both fashion and realism.

Wig Care

Wash every 6 to 10 wears with wig shampoo and cold water. Air dry on a wig stand—never use a blow dryer! Store your wig on a stand to preserve the shape and avoid tangling.

Pro tip: Own more than one wig so each lasts longer and suits different moods. (Don’t ask how many wigs I own! LOL)

Practice Makes Pretty

Wear your wig at home while doing chores, watching TV or getting ready. The more you wear it, the more natural it feels—and the more confident you’ll look in public.

Take Selfies and Ask for Feedback

Use photos to check proportions and silhouette and to see how lighting affects color and shine. Document your evolving style—so you know what works (and what doesn’t). If you're shy, post anonymously in crossdressing or femme fashion forums for feedback and support.

Own Your Look

The most important wig tip? Confidence. 

Whether you’re going for a natural girl-next-door vibe or a glamorous diva look, wear your wig like you mean it. Women and other crossdressers will pick up on your energy more than your hairline.

Caveat Emptor: The preceding tips are synthetic wig centric.

Wearing Teri Jon by Rickie Freeman

Nancy Ng after reading our recent post about French maids.

Women and Their Crossdressers

In an age when gender roles are increasingly questioned and redefined, male crossdressing remains a subject that invites curiosity, confusion and conversation. While society slowly grows more accepting of gender nonconformity, personal relationships—especially with women—often reveal the most complex and emotionally nuanced responses. How do women really feel about men who wear traditionally feminine clothing? The answer is far from simple.

Love and Acceptance: “He’s Still the Same Person”

Many women react to a partner, friend or son’s crossdressing with love, empathy and even delight. For these women, crossdressing isn’t a threat—it’s a facet of identity that adds depth, vulnerability and authenticity.

“He trusted me enough to share something so personal. That kind of honesty only made me love him more,” says Megan, a 42-year-old teacher whose husband came out as a crossdresser after 10 years of marriage.

Some women find joy in exploring femininity together—sharing beauty routines, shopping for dresses or attending drag shows as a couple. To them, male crossdressing is not a deviation but a form of self-expression that challenges rigid norms in a healthy way.

Curiosity, Uncertainty, and the Search for Understanding

For others, the reaction is more tentative. These women aren’t necessarily opposed, but they wrestle with questions:

“Is he still attracted to women?”

“Is this just about clothing, or something deeper?”

“What does this mean for our intimacy?”

Women in this group may feel confused, worried about societal judgment or unsure how to talk about it with friends or children. Their feelings are often marked by a desire to understand, even if that understanding takes time.

“It didn’t bother me morally,” says Linda, 34, “but it was a shock. I had to grieve the version of my husband I thought I knew.”

Mixed Emotions in Romantic Relationships

Wives and girlfriends may feel particularly vulnerable when they discover a partner crossdresses—especially if it was hidden for years. Feelings of betrayal are common, not because of the crossdressing itself, but because of the secrecy.

Sexual attraction can also shift. Some women find their partner’s femininity erotic or endearing, while others struggle to reconcile it with their image of masculinity. This doesn’t make them intolerant—it often reflects deeply ingrained social cues about gender and desire.

“I don’t mind the clothes,” admits Sara, “but when he’s in a wig and heels, I don’t recognize the man I married. I’m still figuring out if I can be attracted to that version of him.”

Toleration with Boundaries

Some women adopt a “don’t ask, don’t tell” attitude. They may tolerate crossdressing as long as it’s private, infrequent or confined to certain contexts. These women may care deeply for their partner but draw boundaries based on their own comfort level or social concerns.

They might say:

“Just don’t do it around the kids.”

“You can dress at home, but not in public.”

“I need you to be my husband most of the time.”

This dynamic often reflects negotiation, not rejection. In many cases, these women are open to compromise but need time, space, or reassurance.

Disapproval and Rejection

Not all women are accepting. Some respond with shame, anger or outright rejection—particularly if they were raised in conservative or traditional cultures.

For them, crossdressing challenges core beliefs about masculinity, marriage and morality. They may feel their partner is “less of a man” or fear judgment from family and community.

In some cases, the relationship ends—not because of cruelty, but because the emotional gap becomes too wide to bridge.

“I couldn’t deal with it. I felt lied to, like everything we had was based on a false image,” says one anonymous ex-wife.

Mothers, Daughters, Sisters: Family Ties and Generational Shifts

Beyond romantic relationships, women also encounter crossdressing as mothers, daughters and sisters. Mothers, in particular, may struggle with a son’s crossdressing—torn between unconditional love and cultural expectations. Some become fierce protectors and allies. Others respond with denial, avoidance or confusion.

Generational attitudes play a huge role: younger women are more likely to embrace or celebrate gender nonconformity.

Daughters of crossdressing fathers often report a mix of embarrassment and eventual pride. Sisters might become confidantes or stylists. In many cases, women within families adjust over time—and sometimes become their loved one’s strongest source of support.

A Personal Journey for Every Woman

Women’s feelings about male crossdressers are shaped by deeply personal factors: upbringing, beliefs, past relationships and how crossdressing is introduced into their lives.

There is no single “correct” reaction—only honest, evolving ones. What’s most important is that these feelings be acknowledged, not dismissed and that both parties in any relationship—romantic or familial—have space for open, nonjudgmental conversation.

In a world where traditional gender roles are giving way to self-expression and authenticity, women’s responses to male crossdressing are more visible, nuanced and vital than ever.

Wearing Boston Proper

Harry McEntire femulating in the 2012 British film Unconditional Love.