The sexiest dress is one that is worn with confidence -- whether you are a man or woman. Men who prefer the look and feel of women's clothing often have trouble finding a flattering look for themselves. Some reasons for this are lack of guidance or an over-reliance on clothing made for women. However, there are some steps you can follow to achieve the perfect look.
Get into the habit of shaving, taking a multivitamin and doing abdominal exercises everyday. Shaving and vitamins will improve the look and feel of your skin, which in turn will give you the confidence to try on a wide variety of clothing, including more revealing styles. Doing abdominal exercises will flatten and tone your belly, which will improve the fit of any piece.
Use the Internet to find specialty stores that sell bras and underwear tailored for men who want to wear female clothing. Having the right undergarments is key to looking good in women's wear. Look for padded bras and padded underwear that will help you fill out curves and control your bulge. Most of these stores are discreet and will deliver your order in unmarked boxes.
When shopping in the women's section of department stores, bring along a supportive female or cross-dressing friend. Make sure to wear the appropriate undergarments as well as any wig or makeup you might normally use. Shopping as a woman with a woman will give you the confidence to deal with sales people or other customers.
While malls and department stores may be great in terms of price and variety, you will often have a more enjoyable shopping experience at a store just for cross-dressing men. These stores have very helpful staff and carry clothes that are made for men, so you're sure to find a great look and fit.
Maintain a basic wardrobe of A-line dresses and pant suits that you can fall back on for days when you don't feel like dressing up to the hilt. Getting into the habit of wearing simple women's clothing will gradually make you feel more comfortable in evening wear and formal wear.
Always do little things that will make you feel more feminine. Wear lingerie under your clothes, lipstick, earrings, heels or a wig to bring out your soft side. Whatever you're wearing, hold your head up high and smile.