Most of my shopping I do in “drab” mode. My wife and I like to spend time together browsing the second-hand stores or the clearance areas of department stores. She likes that she doesn’t feel rushed since I don’t get bored and impatient like most husbands. She doesn’t mind that I will look for women’s clothes for myself even though she prefers not to see me dressed in them. Second-hand stores are great because you can get a lot of items for a little money, don’t get harassed by sales staff, and have changing rooms that are usually not strictly attended. Of course the down side is that you rarely get newer styles and the items may be imperfect. I've bought a few things over the internet at sites like Glamour Boutique but prefer to buy things in person,
Many cross-dressers have no compunction about shopping anywhere no matter if people are aware they are shopping for themselves or not. But I think I am like most CD’s in that it still makes me a little nervous. From October through early February there is the built in excuse of the holidays (Halloween costume, Christmas present, Valentine’s present) that make shopping for women’s things a little easier. It’s funny; it doesn’t matter what time of year it is, if I’m actually shopping for something for my wife, I am quite comfortable shopping for any women’s articles but if I’m shopping for the same thing for myself I feel like everyone knows exactly what I’m doing.
Depending on how I’m feeling I will usually just buy things without trying them on but if I need to I will take women’s clothing into the men’s dressing rooms. I even did that with wedding dresses a few times. I did a blog post about that.
If I’m feeling a little nervous I might grab a suit jacket and drape that over a feminine item that I’m bringing into the men’s dressing room.
A few times I have shopped enfemm. I take the advice of most CD’s that have done it and have dressed down since that’s what most GG’s do when shopping. I’ve not had any problem going into the ladies dressing rooms and was even directed to the ladies dressing room when I approached a men’s dressing room that was not clearly marked. I find if you just act like it is perfectly normal and are polite to everyone then the probability of an incident is limited.
While there are various reasons that men like to crossdress, the goal is usually to create an illusion that conceals the masculinity and creates an image of femininity. However doing this in a stylish way can be challenging. Some of the most fun I have is to take out all the clothing items I own and pair them in every possible combination until I find an outfit that I think works. And judging by the state of my daughter’s bedroom, she does this same thing every day.
That can be very time consuming and there are better ways of putting together an outfit. Whether planning on going out shopping on Rodeo Drive or just dressing for the mirror at home it helps to try to take several factors into consideration even if they are purely fictional. First you have to consider the season and temperature. Also, the outfit should also be appropriate for the expected activity. Will those heels still feel comfortable after an hour of shopping? One of the fun choices is to get to pick a mood; do you feel like you want to blend in, be casual, feel girly, or be a sophisticated pretty woman. Finally, the outfit should be as flattering as possibly. Be sure that none of the pieces of the outfit are obviously contradictory to another. Luckily, most things can fit into multiple categories.
Even after taking all those ideas into account it can still be difficult to know what pieces to put together. A safe place to start is with solid, neutral colors (or demim as it can be paired with almost anything). A lot of women start and end here but that can be boring and as a cross-dresser you probably want to take advantage of more feminine designs to enhance the illusion. Simply adding one fun item to any solid, neutral outfit can take it from boring to stylish. Exchange the top or bottom for one that is bright colored, patterned, ruffley, tight, or baggy. Make sure it is just one item. You can even do this by trading out the shoes for ones that are colored or patterned if you balance the color in a top or necklace of the same color.
Watch out for certain pitfalls that are easy to fall into. Just because those shoes are soooo cute and that skirt is just beautiful doesn’t meant they should be worn together. Nylons make your legs shapelier but despite Kate Middleton’s lead, they aren’t worn as much as they used to be and should never be worn with open toed shoes or casual outfits. Black nylons generally should not be worn with anything but black shoes and a dark dress. Be careful about dressing too young or trendy.
A good way to compile a series of outfits that you can call up is to take pictures of the ones that look good. When you buy a new article of clothing, play with it and see how you can dress it up or down. Often an outfit can seem good when you put it together but later when you look at the picture more objectively you how it doesn’t quite work.
Like all of these guidelines there can be lots of exceptions and finding those exceptions can be a lot of fun too. Just be sure to leave plenty of time to clean up the mess when you’re done.