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 Рwidest point where the derri̬re 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.
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| Wearing Boston Proper |
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| Alan Manson and other gentle men femulating in the 1943 film This Is The Army. Click here to view this film on YouTube. |
