How to Buy a Dress (For Men Who Crossdress)

Here’s a practical and confidence-boosting guide for men who crossdress and want to buy a dress—whether it’s your first time or your fiftieth. The key is to blend self-expression with smart shopping

Know Your Measurements

Women’s clothing sizing varies wildly between brands. Before one even dares slip into a dress, he must first become acquainted with his own proportions. Skip the guessing and arm yourself with actual numbers:

Bust – measure around your chest at nipple level (the fullest part of the chest).

Waist – narrowest part, just above the navel. (A proper lady always knows his waistline.)

Hips – widest point where the derrière declares its presence.

Shoulder Width and Height – helpful for dresses with sleeves or longer lengths; we often need just a smidge more room up top.

Tip: Keep a cheat sheet on your phone or in your handbag for easy reference.

Start with Stretchy Fabrics

If you’re new, try jersey knits or anything with spandex—they’re forgiving, flattering, and easier to fit over broader shoulders or a flatter chest.

Pick the Right Styles

Some cuts are more crossdresser-friendly than others:

Wrap Dresses – Adjustable fit and a waist-accentuating shape (ever-so forgiving).

Empire Waist – Flows from below the bust, a dreamy favorite, especially if one’s middle is still more lad than lady.

A-Line Skirts – Cinches the waist, swishes at the hips and thighs without clinging.

Fit & Flare – Feminine silhouette without being tight all over.

Avoid tight sheath dresses or tailored shifts until you get the hang of sizing.

Shop Smart (and Safe)

Worry not —many modern establishments now serve the gentler gent with discretion and charm.

Online – ASOS, ModCloth, Torrid (for curvier fits), Amazon, Shein and eBay offer privacy and range. Just check return policies.

In-store – If you’re comfortable, stores like Target, Macy’s or H&M can be welcoming. Go during quieter hours or bring a friend and do watch for curious sales associates.

Thrift Stores – Great for experimentation on a budget—and nobody bats an eye.

Pro moves: Visit mid-morning on a weekday; the aisles are quiet and the sales associates more patient. Also use self-checkout or order online with in-store pickup.

Try It On (Privately or Publicly)

If you're trying in-store, you’re legally allowed to use the fitting room matching your gender identity in many places—but know your local laws. At home, always try on standing and sitting—some dresses ride up. (A lady should always sit in her dress before committing. How else will she know if she can cross her legs properly?)

• Many fitting rooms are open-minded, but discretion is the better part of fashion.
• Bring a companion if nervous (a mother, sister or sympathetic wife is ideal).
• Try on with modesty. Always wear clean underthings.
• Check yourself from every angle. Twirl at least once.

Tip: Snap mirror selfies to get a full view—what feels good often looks even better than you think!

Support the Illusion

No ensemble is complete without the proper trimmings:

Shapewear for curves; waist cinchers and girdles tame the tummy and flatter the fanny.

Padded panties for a little oomph below the belt.

Breast forms, optional, but marvelous under a snug sweater dress.

Heels or ballet flats to complete the look

But remember—you don’t have to “pass” to be beautiful.

Confidence Is Your Best Accessory

You deserve to feel good in whatever you wear. The more you shop, the more natural it feels. Dress for yourself.

And hold your head high, your hemline modest (or daring, depending on the occasion) and your self-doubt firmly in the past. Whether you’re dressing for housework, hostessing or a heavenly night on the town—do it with pride, polish, and just a touch of perfume.

Wearing Boston Proper

Alan Manson and other gentle men femulating in the 1943 film This Is The Army.
Click here to view this film on YouTube.

Stuff 75: Confidence

By J.J. Atwell

Are you confident in your femme presentation?

Over many episodes of Stuff, I’ve talked about how you present in public and the role that your confidence plays in your believability. Did you take that to heart? How do you honestly feel?

I’m mostly confident

I’ve felt my confidence grow the more that I get out as JJ. Usually, once a month I’m out to a group meeting. That could be a safe, private venue like our clubhouse location. Little pressure there. Or it could be a public place like a restaurant for a Girls’ Night Out. A bit more pressure there as you are now out where you and your sisters are all easily seen and judged.   Surviving several of those evenings did wonders for my confidence.   

Going even further, JJ has gone out to a couple of stage shows. Doesn’t sound like a big thing, does it? You just sit there in the dark watching the stage, right? Yes, that part is true, but you need to get to that seat in the first place. That means passing through metal detectors and ticket collectors, then mingling with the other patrons waiting for the doors to open. Even greater pressure is intermission where everybody heads to the restrooms. Surviving a couple of those experiences gave me more confidence when going out. 

But I’m not there yet!

You would think that with that level of experience JJ would have become very confident. Well, she thought she was. Then she got an invitation from a couple of my good, well accomplished, CD friends to go out for lunch and shopping in a nice, artsy community. 

For some reason, the thought of that scared me. Out milling amongst the general public with two other CD’s and our SO’s. Could JJ pull it off? She wasn’t sure she was ready for that. As I write this, I’ve pretty much convinced myself to go ahead and push the envelope further. I’ll report back on how this turned out in a future Stuff.   

I’ll be back

I’ll be back with more Stuff for sure. Comments are welcome either here on the blog or by email to Jenn6nov at-sign gmail dot com. JJ is always looking for more stuff, so let me know what you would like to read about.

Wearing StyleWe

Sharman Joshi and Sahil Khan femulating in the 2001 Indian film Style.

Happy Father’s Day

Boob Banter

Two 20-something ultra-feminized besties or “male ladies,” Kylee and Braydenne, chat over matcha lattes at a café, casually debating the next “natural step” in their journeys under the matriarchy:

Kylee (stirring his drink with a manicured finger): Ugh. So I tried on that lilac blouse I got from FemmeForm last week and honestly? It just hangs. No shape. I’m starting to think the girls need a little… boost.

Braydenne (sipping delicately): You mean surgical boost? Oh my goddess, Kylee. That’s a whole level of commitment. Like, silicone-serious.

Kylee: Okay, but hear me out—Tyler at HR already got his done and ever since? He radiates. He walks like a woman who knows she’ll never wear a blazer again.

Braydenne: True. His posture improved like, immediately. And he’s up two cup sizes and one pay grade.

Kylee: Coincidence? I think not. Plus, his wife threw him a “Boob Reveal Brunch.” I’m still jealous of the almond champagne.

Braydenne (twirling a strand of his highlighted hair): Yeah, that part looked cute on the Gram. But still. Surgery is big. My mom-in-law would freak—she already made me wear push-ups to her garden club so her friends would think I was “coming along.”

Kylee (smirking): Mine offered to pay if I went C-cup minimum. She said, and I quote, “We didn’t vote in the matriarchy just to have flat-chested sons-in-law.” Classic Linda.

Braydenne: Iconic. You always get the cool in-laws. Mine are still stuck in the “just feminize him gradually” phase. Like I don’t already own three sports bras and cry during mascara commercials.

Kylee: Look, I’m just saying—I want my tops to pop. And honestly, I think I’ve earned it. I’ve done the skirts. I’ve done the waxing. I’m tired of stuffing.

Braydenne: Valid. Though I do love a good falsie on casual Fridays. Low effort, high jiggle.

Kylee: Babe, imagine never having to tape again. Just a built-in bounce. Bras that fit. Boys would blush when we walked by.

Braydenne (pretending to fan himself): Okay, sold. Let’s at least get consultations. Worst case, we do a “try-on” party with those silicone demos and some wine spritzers.

Kylee: Yessss. And maybe I can finally fill out that peplum top without looking like a sad shelf.

Braydenne: To boobs?

Kylee: To boobs.

(They clink matcha glasses.)

Wearing Beulah dress and Saint Laurent bag

James Brown, Nigerian femulator

Gift Guide Gurl

Wearing Ann Taylor

Fathers’ Fashion Show

The Beach Boy Died Today

I love music. Last time I looked, I had over 15,000 songs stored on my computer. A lot of rock, but most other genres, too, but definitely a lot of rock.

My interest in rock music was kindled by The Beach Boys’ surfing music and the person most responsible for that music, Brian Wilson, died today. 

Bummer!

I am very sad about Brian’s death, but on a positive note, he will be rejoining his brothers in heaven.

So be it.

Father’s Day Gift Guide

What to Buy Dad as He Embraces a More Feminine Future

Father’s Day is upon us once again — but in today’s enlightened, equality-forward world, the classic Dad Gift Guide needs a serious style refresh. After all, many modern fathers are on a transformative journey: stepping into softer fabrics, letting go of outdated masculinity and embracing the joys of feminization — whether for work, wellness or wifely encouragement.

Here’s our lovingly curated guide for what to get the evolving Dad — whether he’s just begun shaving his legs or has already mastered the daily tuck-and-blend.

🎀 The Introductory Intimates Set

Recommended: The “Blushing Basics”™ Kit from ObeyNights Lingerie Co.

Help him start from the inside out. This tasteful starter pack includes a lace-trimmed bralette, high-waisted control briefs and a satin sleep camisole — all in understated tones of blush, dove grey and obedience beige. Perfect for the dad who’s just traded boxers for beauty.

👠 Sensible Starter Heels

Recommended: “Heel Me Softly” Kitten Pumps (2-inch heel, reinforced arch)

Heels don’t have to hurt — especially when Dad’s still learning how to descend the stairs like a debutante. These ergonomically-designed pumps are both training tool and fashion statement. Bonus: Comes with matching foot soak and padded inserts.

💄 His & Hers Makeup Mirror

Recommended: The “Face Forward™” Vanity Kit (With Coaching Cards)

Support his new skincare and makeup routine with a dual-sided lighted mirror and laminated guide featuring helpful affirmations:

• “Yes, that’s your shade.”
• “Confidence is the best contour.”
• “Blending is obedience.”

👗 The Wrap Dress: His First Real Outfit

Recommended: “ComplyChic™” Jersey Wrap by SurrenderWear

Flattering, forgiving and just formal enough for family brunch. Comes in sizes for Dads still adjusting to hormone shifts and sits comfortably atop a padded shaper. Many wives report this is the first outfit their husband genuinely wanted to twirl in.

📚 Reading Material for the Reforming Man

Recommended Titles:

• “From Father to Femme: My Journey in Flats”
• “Boys Who Obey: Raising Sons in a Matriarchal Household”
• “Pressed, Dressed and Blessed: 30 Devotions for the Submissive Spouse”

Gift him the wisdom of other husbands who walked before him — often in matching ankle boots.

🧼 A Scent of Surrender

Recommended: “Demure Dusk” Fragrance by HerWill™

Notes of lavender, civility and vanilla musk, designed to subtly reinforce his softening mindset. Spritz after morning chores or before reporting to the matriarch.

📅 A Personalized Chore Collar & Weekly Planner

Recommended: “The New Honey-Do You Understand?” Set

Includes a custom-embroidered lace collar ("His Grace is Her Gratitude"), plus a floral-print daily planner pre-filled with tasks like:

• “Steam Her Blouses”
• “Practice Kneeling Posture”
• “Evening Wig Care & Reflection”

🧸 Bonus: For the Kids

Have the little ones present their father with a handmade “I Love My Sissy Daddy” card. Include space for glitter, lipstick kisses and a checklist of favorite shared activities:

☑️ Shoe Shopping

☑️ Practicing Curtsies

☑️ Watching Matriarch Manor™ together

No matter where Dad is on his feminization path — tentative steps in tights or already navigating brunch in ballet flats — a thoughtful, tailored gift can show your support and love. Celebrate him for the graceful figure he’s becoming, inside and out.

Happy FemFather’s Day! 💐

Wearing Bebe

Loretta and Veronica, circa 1962

Another AI and Photoshop creation of a vintage crossdresser photo with an early 1960's, Casa Susanna look.

Stuff 74: Bling

By J.J. Atwell

Do you bling?

When you get dressed do you include some bling in your outfit? How much do you use? What kinds of bling do you use? Is it enough? Too much?

Three Bling Rule

Have you heard about the Three Bling Rule? I hadn’t until my friend Gigi brought it to my attention. Nancy Joseph is the proponent of this rule which you can read more about by clicking here.

For those who don’t want to click on that link or bother reading her story, I’ll try to summarize. It boils down to: you need to count up your bling, because you are allowed only three “bling points.” And be aware that some things count as more than just one bling point. For example, sparkly earrings are one bling point, but a sparkly dress would be two bling points. Some other rankings:

• bold necklace (1 bling)

• shimmery metallic sandals (1 bling)

• cocktail ring (1 bling)

• shoes or bag (1 bling)

• jeweled cuff bracelet (1 bling)

Remember also that location matters in that you don’t want to have two bling points in close proximity to each others.

Are you a rule follower?

I’m not sure I agree with the Three Bling Rule. As much as I try to dress to blend, I’m a sucker for bling. Towards that end, I need to spend a bit of time thinking about my outfit and accessories. Not only does the outfit have to be harmonious between colors, patterns and textures, it also has to blend with what you see women wearing around you. It’s not easy being a CD!

I’ll be back

As always comments are welcome either here on the blog or by email to Jenn6nov at-sign gmail dot com. JJ is always looking for more stuff, so if there is something you would like to read about please let me know!

Wearing Joseph Ribkoff

Harvey Korman femulating (again) on television’s The Carol Burnett Show.

Any Color As Long It’s Red

By Monika Kowalska

Red lipstick boasts a rich history, evolving from ancient adornment to a modern symbol of empowerment. Recent archaeological findings revealed a 4,000-year-old vial in Iran containing pigments similar to modern lipstick, demonstrating the enduring legacy of bold lips. Ancient queens like Mesopotamia’s Puabi and Egypt’s Cleopatra used vibrant lip colors to signify status and power, while in ancient Greece, red lipstick was associated with sex workers.

Over the centuries, red lipstick’s meaning shifted dramatically. In medieval Europe, it was viewed as wicked or even linked to witchcraft. Queen Elizabeth I revived its popularity among the aristocracy, but later, its use was stigmatized and even criminalized. In the 20th century. Red lips became a symbol of feminist rebellion, especially during the 1912 suffragette marches and later, of patriotic femininity during World War II. 

From Hollywood icons like Marilyn Monroe to contemporary figures like Taylor Swift, red lipstick has remained a beauty staple. Today, it continues to serve as a bold political statement, seen in protests in Nicaragua and Chile, reinforcing its enduring power as a tool for self-expression, defiance and identity.

There’s something almost magical about red lipstick. The moment it touches my lips, I feel transformed, bolder, sexier, more me. It’s not just makeup, it’s armor, it’s rebellion, it’s romance. And over the years, red lipstick has become my signature, my ritual, my unapologetic wink to the world. 

I wasn’t always brave enough for red. Like so many of us, I started with soft pinks and glosses, dipping my toes into femininity one sheer swipe at a time. Red felt too loud back then, too “look at me,” too dangerous. But the first time I dared to wear it outside the safety of my bedroom mirror, something changed. I saw a woman looking back at me, confident, elegant, a little mischievous. I fell in love.

What I adore most is how versatile it is. A matte red can make you look like a 1940s starlet, a glossy cherry evokes summer nights and clinking wine glasses and a deep crimson whispers secrets in candlelight. Red can say “I’m in charge” or “Kiss me” or sometimes both at once. Isn’t that delicious?

I remember one summer rooftop party in particular. I was wearing this little black off-the-shoulder dress, nothing too flashy, but the red lipstick? She stole the show. I caught the eye of a woman across the terrace. She walked over, introduced herself, and said, “I only came to tell you that your lipstick is doing everything right.” We ended up talking for hours under string lights, sharing secrets and sipping rosé like we were old friends. That’s the power of red, it starts conversations, turns heads, opens doors. 

Of course, there are rules, finding the right shade, prepping the lips, perfecting the cupid’s bow. But honestly? Sometimes I break the rules. I blot it with a tissue when I want that just-kissed effect. I swipe it on with my finger when I’m in a hurry and want that effortless, Parisian smudge. Red lipstick doesn’t have to be perfect. It just has to be you.

When I wear red, I don’t hide. I strut. I take up space. I laugh louder. I flirt more. I remind myself that I deserve to be seen, to be heard, to be desired. Even on days when I’m tired or doubtful or wearing the same pair of jeans for the third time in a row, red lipstick shows up for me. And I show up for her. There’s an intimacy in applying it, too. That slow swipe across the lip, the soft press of tissue, the little dance you do in the mirror after. It’s a ritual, a flirtation with yourself. And honestly? I wish every woman would fall in love with that moment.

To all of you reading this, whether red is already your go-to or still sitting untouched in your makeup drawer: try it. Try it on a random Tuesday. Try it when you’re cooking dinner. Try it when you’re crying and need a pick-me-up. Let that red speak for you when you’ve forgotten how. And if someone says, “Wow, that’s bold,” just smile. Say “Thank you,” and mean it. Because darling, so are you. 

Here’s to red lips and all of you who dare to wear them. 💋

Monika has been interviewing trans people in her blog, The Heroines of My Life, since 2013. Click here to see who she has interviewed lately.

Wearing Boston Proper

Carlotta, circa 1963

Playing with AI and Photoshop over the weekend, I tried creating vintage crossdresser photos with an early 1960's, Casa Susanna look. Carlotta (above) was my first attempt. 

The Modern Male

Fashionable Fellows