Five fashion tips for plus sized men who want to dress like woman

Approximately half of all American women are over a size 14, which is considered to be “plus-sized” by the fashion industry. This is good news for crossdressers as it means more stores catering to the larger woman. Personally I’ve flirted with size 14, but spend most of my days between size 16 and 18.
If you’re still trying to understand how woman’s sizes work, take a look at this cross dressing size chart a few months ago.

Crossdresser Clothing

Overweight women want to look as good, stylish, and put-together as their “regular”-sized counterparts. In the typical department store, the selection appears to be quite divergent. The misses department displays stylish, budget-friendly options. The plus-size, or women’s, section shows high-waisted pants, tunic-style shirts, and sack-like dresses. And transvestite fashion seems to be enamored with spike heels and mini-skirts.

What is a crossdressing man with fashion sense to do?

Janet Perry, a plus-size 50-something and author of Bargello Revisited, shares some tips for making plus-size fashion fashionable:

  1. Educate yourself: Pay attention to what’s fashionable in fashion magazines, on TV, and in everyday life. Doing this shows you what trends are in and what is (or should be) out. Eventually, you will be able to spot the trends and know what’s fresh without having to be told (via magazines or TV shows like What Not to Wear on TLC).
  2. Know your own body: What is your shape? Do you have an hourglass figure or a square? An inverted triangle or a pear? How do you find out? You could have a figure analysis by a fashion consultant or you can figure it out for yourself. Hold a yardstick against your shoulder and your hip. In looking in a mirror, does the yardstick angle in or out? Does it stay straight up and down? If it goes in, you’re the inverted triangle; out, the pear. Straight? Either a rectangle or an hourglass. How do you tell the difference on that just based on the yardstick? See if you can put any fingers between the yardstick and your waist without moving the yardstick. If you can get at least two fingers between there, you’re an hourglass. Look for clothes that flatter that shape instead of hiding it.
  3. Know your colors: Perry advocates, “Have your colors done and stick to them.” However, knowing if you look better in cool, warm, or neutral colors will work well enough. To discover that, you need a swatch of shiny silver fabric, shiny gold fabric, and a mirror. Hold each of them in turn up to your face, right under your chin. How do you look? If the silver makes you look washed out but the gold makes you look healthy, stick to warm colors. If it’s the other way around, use cool colors. Both? Technically, you’re neutral, but you can wear cool or warm colors within reason.
  4. Accessories and shoes don’t come in plus sizes,” Perry says. Wear classic clothes that fit well and look good on you and indulge in the trends through your shoes, purses, and other accessories. Our crossdressing fashion sense should kick in at this point, as we realize that closed shoes and lower heels are the way to go if we want to be more passable.
  5. Avoid things that signal you don’t care: Sweatpants never stay looking nice. T-shirt dresses with no shape, pants that are made to look like dresses, and dresses or skirts that are too long make you look frumpy and heavier. No plus-size woman wants, or needs, that. Perry also says, “Muumuus don’t even look good on thin, beautiful Hawaiian girls.”

It is possible to be fashionable on a budget. Some stores, such as Lane Bryant, Fashion Bug, Katherine’s, Avenue, and Cato Fashions, to name a few, offer selections that are fashionable for plus-size women at various budget-friendly prices. An outfit (three separates) for an awards banquet, for example, recently cost less than $60.00 at Cato Fashions.

If you’re still having trouble you’ll find crossdresser fashion advice and more in this guide. Be beautiful!


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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14 years ago

I am 6’4″ 230LB and I am interested in the sizeses of womens cloths that I shoud wear. I wear a 42 or 44 C bra. I do not know what size of dress and shoes I should buy. Can you help me get started. Thank for you time.


7 years ago

I’m so new to all this I feel overwhelmed at times and excited at others. I’m pretty lucky to have a understanding wife that helps and supports me. But still I’m 6 foot 260lbs and my butt puts jlo to shame just point me in the right direction I plan on going out into the world the first time in February

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7 years ago

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6 years ago

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6 years ago

Thanks a lot for sharing this with all of us you actually
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6 years ago

Hello, after reading this amazing post i am too happy to share my knowledge here with

Donna Jewel
10 months ago

Hi, this pass week I dressed and went out, has been too long.I went to Sephora and everyone their was welcoming and friendly.Received makeup tips and bought some
makeup.It was so good to be a woman again!! Thanks for reading this.


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