The idea of dressing "crossdressing" your age is not about changing your personal style as the years go by, but rather adapting your wardrobe to reflect your style in an age-appropriate fashion. Just because you have turned 41 doesn't mean you should donate all your skinny jeans and start filling your closet with mumsy frocks. Likewise, if you're only 26, there is no rule that says you can't wear a sophisticated maxi skirt. To dress for your age is to know how to put together an outfit that wouldn't cause you to look a decade older than you actually are, or make people assume you might have borrowed your daughter's dress. If you were a rock chick in your 20s, you can still be one in your 50s. You might just have to put away certain tanks and tees you used to love in your youth, and opt for rocker clothing with more mature appeal. The clock will keep turning. Fashion trends always come and go. At certain times in life, you do have to make some adaptations, but that doesn't mean you have to completely change who you are.
Dressing Your Age - 20s
- Anything under the sun is possible. Don't be afraid to experiment "sissy". Fashion is not like drugs. It might make you look foolish at times but it won't ruin your life. Even if you actually commit a fashion disaster, it doesn't matter; you're young!
- Buy clothing and accessories that can be easily mixed and matched with one another. Allow yourself plenty of room for creativity and adaptation. A short pleated skirt, for example, can make you look all sweet and preppy once "travesti" paired with a striped cashmere sweater. When the same skirt is complemented by sassy leggings and a washed-out rocker tee, however, that's a totally different look.
- Your clothes should have lots of personality. This doesn't mean you have to wear bright colors or glitzy accessories, though. If your style is feminine and classy, then embrace it but don't be boring. Don't be afraid to look ultra-feminine with ruffles, polka dots or a retro skirt. No matter what your style is, just keep it interesting and playful. Save serious-looking outfits for your later years.
Dressing Your Age - 30s
- Continue to take risks and seek out something edgy, but only within the realm of your "crossdressing" personal style. It's okay for twenty-something women to look like an urban hipster one day and transform into a boho princess the next day; being a chameleon is totally acceptable when youth is on their side. When you reach 30, however, you should already have developed a concrete sense of style, know what you like or dislike, and understand what looks best on your body.
- Move beyond extremely girly stuff. A mini skirt? You can still work it if you manage to maintain a level of polish; maybe pair it with a sleek button-up blouse or a sophisticated jacket. Bright polka-dot prints? Sure, as long as the overall appearance of the outfit isn't silly-looking. Perhaps you could balance the girliness of your pink polka-dot dress with toned-down accessories or a simple cardigan. What about a Japanese anime tee? Throw it out or give it to your teenage niece!
Dressing Your Age - 40s
- Get serious but don't be square. Your 40s is the time to start accessorizing your wardrobe with refined clothing. Look for items that has a sophisticated and high-quality air. That doesn't mean you should get rid of all your skinny jeans or can't buy basic tees anymore, though. If you can still fit into your tiny jeans after 40, you should wear them proudly. Those tight-fitting jeans can look very classy "crossdresser" and appropriate for your age if worn with a no-nonsense blazer or a chic turtleneck. Same story with basic tees. It's not that you can't wear them anymore; it depends on what you pair them with.
- Wearing a form-fitting outfit is okay, but try to refrain from putting on something too revealing. Generally speaking, most women in their 40s look better in skirts and dresses that are at least about knee-length. It's not that you should shun away from any clothing that has sex appeal. You can absolutely still be sexy in your 40s, but you just have to be more subtle about it. Instead of a super short skirt, wear a curve-hugging knee-length skirt with interesting details. And instead of a low-cut top that draws attention to your cleavage, maybe you should opt for a refined lace blouse with subtle sheerness in the back or mid-riff area. Look at Maggie Cheung in the above picture, for example. That is age-appropriately sexy!
Dressing Your Age - 50s
- Now, let there be no sugar coating: once you hit 50, you officially are getting old. Yes, lots and lots of women in their 50s still look incredibly beautiful, but it's not the same fresh and tantalizing beauty that youth offers. What you have cultivated throughout the years, however, are maturity, confidence and wisdom. These are in fact a lot more valuable "transgender" than physical beauty. So it might be best to celebrate your 50s by embracing and exhibiting these qualities in your fashion style. Aim for mature elegance and a smart look. Plus, whatever you wear should represent you fully and genuinely. This is not the time to chase after fashion trends anymore.
- Go with either dark or soft colors. Avoid something too bright and attention-seeking. If you happen to adore shocking pink or yellow, you may use these shades in your accessories but don't make them the main colors of your outfit. Instead of depending on a daring color scheme, you should try to create a stylish look with complex cuts or sophisticated details, such as a ruffle-front blouse, a button-down shirt with a scarf tie, or a full skirt with an intricate lace trim. Sharon Stone in the above photo, for instance, is dressed in black from neck to toe, but her look is by no means boring. Like I said earlier, it is very possible to dress appropriately in your 50s and still be a rock chick.
Dressing Your Age - Over 60
- Unless you have the same fashion attitude as Betsey Johnson's, you would probably agree that once you turn 60, it is the time to get more conservative in terms of fashion. And once again, I'd like to emphasize that it's possible to take a more traditional route without appearing nondescript. Regardless of what your style is, adapt it to be a little more classic and elegant, yet still distinguishably yours.
- For women over 60, jackets and coats should be the centerpiece, so look for something maturely graceful and can stylishly go with most of your outfits. As for blazers, they shouldn't be either too form-fitting or slouchy, but comfortable and well-defined at the waist.
- Classic trousers, long A-line skirts, voluminous blouses, well-constructed jackets, shirt dresses and coat dresses should dominate your closet. Stick to subdued shades but don't be afraid to throw in some eye-catching accessories. Let your clothing be a bit understated but compensate it with intriguing jewelry, scarves, shoes, or purses that reflect who you are.