With a Little Help from Her

For years, women have been helping the men in their lives dress better. A wife might select her husband’s tie, replace his worn-out shoes or gently suggest that his favorite shirt passed its expiration date sometime during the previous administration.

Lately, however, some women seem willing to take that assistance a few steps further and more men seem willing to follow.

Instead of steering him toward another gray suit or pair of khakis, she may wonder how he would look in a skirt. She may hold up a dress and announce, “This color would be perfect on you.” Before long, she is introducing him to hosiery, heels, jewelry and makeup. What began as a playful experiment may develop into a complete feminine makeover.

The surprising part is not that women enjoy doing it. Many women have years of experience coordinating outfits, applying makeup and choosing flattering hairstyles. Transforming a willing husband or boyfriend gives them an opportunity to use all that knowledge on a brand-new canvas.

The real surprise is how many men are willing, even eager to become that canvas.

Some have secretly wanted to wear feminine clothing for years but lacked the courage to say so. A woman’s invitation provides both permission and encouragement. Others may never have considered feminization until a wife or girlfriend suggested it. Once they see themselves in a flattering dress, expertly applied makeup and an attractive hairdo, their resistance sometimes disappears along with their trousers.

Women also tend to feminize men differently than men feminize themselves. A novice femulator left alone in a dress shop may gravitate toward the shortest skirt, highest heels and biggest breasts available. A woman is more likely to consider his age, figure and destination. She knows that successful femininity is not merely a collection of exaggerated female symbols. It is a complete presentation.

She may tell him that the tight red mini is inappropriate for lunch with her friends, then put him in a wrap dress that flatters his figure. She may replace his enormous wig with a believable pageboy, reduce the makeup and teach him how to walk naturally in sensible heels.

In other words, she may transform him from a man wearing women’s clothing into a presentable woman.

Trust is an important part of the process. Allowing another person to reshape your appearance can make you feel vulnerable. When a man permits a woman to choose his clothes, apply his makeup and guide his behavior, he is placing himself in her capable hands. When the experience is affectionate, voluntary and respectful, it can bring a couple closer together.

The woman may also discover that her feminized man is a delightful companion. He becomes interested in shopping. He notices her new shoes. He understands why getting ready takes longer than five minutes. He may even stop complaining about the number of dresses in her closet after realizing that he has begun filling another closet with dresses of his own.

Of course, not every man wants to be feminized, and no one should be pressured into it. But traditional rules governing what men may wear are gradually losing their authority. Younger generations in particular seem less frightened by clothing, cosmetics and styles once reserved exclusively for women.

As those boundaries weaken, more women may feel free to suggest feminization—and more men may finally feel free to say yes.

Sometimes all a potential femulator needs is an invitation from the woman he loves:

“Sit down, dear. I want to try something.”

And if she knows what she is doing, he may soon be asking when they can do it again.

(Thank you Emma Davies for your comment which inspired me to write this post.)

Wearing Shein

Veit Alex, model