Overcoming Shopping Anxiety: How to Shop for Feminine Clothes with Confidence

As part of transforming or getting ready, a crossdresser needs clothes. While online sites are good, nothing beats shopping in person.

Know Your Size Before You Shop

Knowing your size and budget helps to find items that will make you feel wonderful. The best thing to do is to research ahead of time before putting yourself out there.

Many clothing stores have measurement conversion charts to help you find your size. If you have larger breast forms, you may need to get a larger size of top or blouse. Hip pads will require larger sizes, especially pants. Skirts have a bit more tolerance for wearing different sizes, but you should still be aware of what size fits best.

Plan Your Look

Before going to the website or getting out the door, you should roughly know what look you want. I have a folder of outfits I have seen across the web that I save for reference.

I also have several store web pages saved, with wish lists of items I want. If you keep an eye out and actively monitor sites, you may find big discounts when sales happen!

Some sites have filters for the shape, color, and focus of listed items. Play around with filters to see if there are any patterns in what you like to help shape further searches.

Even if you have found your correct sizing, don’t be afraid to search outside those size ranges. Some items may be out of stock, but you can still wishlist them to be notified when they are back in stock.

Scouting Out a New Store or Website

Google search lets you search for an image of an outfit to find places to buy it. If you have photos of outfits you like, put them into Google Images to search for suppliers.

If you find a store with which you are unfamiliar, look it up for reviews. The ratio of good to bad ratings is a good indicator of the store’s quality.

When making your first purchase from a store, I recommend not buying too much at once. Buy a few items on sale to learn more about the store’s quality. Once you receive them, you should be able to buy more with little worry.

Shopping In-Person: Preparation Is Key

Know What to Expect

When looking to buy clothes in person, there are several questions to ask. Is this a store in your town, or are you out of town? If you are shopping out of town, is it a chain store that you are familiar with, or is it one you are unfamiliar with?

Familiar stores out of town can be good to go to as people may not recognize you. But they can also be scary to navigate if not 100% confident. You are never sure of how the cashiers and employees are with trans and crossdressers.

In general, if a store is a branch of a chain of stores, it will be approachable to both femme and non-femme. It can be a little harder to tell with local stores and smaller chains, which can have a wider range of attitudes to cross-dressing.

Some stores may openly support crossdressing. These can be good to watch, as they can make shopping a more pleasant experience.

Preparing Your Look

Once you have settled on a store, you should prepare for the day. If you are going femme, it can be a good idea to understand the normal shoppers at the store.

As part of scouting, find out what the regular customers wear there. This can help you tailor your outfit to make you comfortable shopping, among other things.

You may have previously also checked the time the store was busy. On the day, recheck how busy it is to see if it has changed.

If you have a normal preparation routine for going out, now is the time for it. Readers who have read about my routine will know mine roughly: shave face, shave body, moisturize, etc.

Putting together an outfit is my favorite part of it all. From your previous research, you may have an idea of how the average shopper dresses at the desired store.

You can absolutely put together a more elaborate, colorful outfit for the occasion. For many people, dressing femme is a critical part of their identity.

If you do make an elaborate outfit, depending on where the store is, you may get some attention for it. If that is something you don’t mind or actively love, enjoy it! I am quite shy in public, but I still try to incorporate things into an outfit to make it nice.

Personal Preparation Before the Trip

Going out in public while femme is such an exhilarating experience. It’s fun to look good, even if you wear a modest outfit. It is very fun to wear something cute or boho, though.

If driving, make sure your shoes are suitable for driving, or take your nicer shoes with you until you arrive. I love pretty shoes. My favorite pair are mule shoes with a black velvet wrap. But I know that they are in no way good for driving, so I carry a pair of black ballet flats to drive in.

Walking to the store can also be fun. It helps lengthen the time you can be yourself and gives you a sense of being part of the town or city. There have been a few times when walking has meant I encounter nice people or find other stores—places I wouldn’t have otherwise found if I had driven or taken a faster way there.

Be polite to people on your way there. Build up charm and positivity on your way there so that when you arrive, you are in a good space.

Confidence is Key: Shopping in the Store

Be Bold, Polite, and Confident

Be bold, polite, and confident. Most of the time, the store worker is focused on giving you a good shopping experience. Provided you act as another normal customer the experience should be good.

Several countries also have laws to protect people from discrimination, which can make shopping easier.

If you have done research, you should be able to find what you need. You can have a good time out shopping, but not loitering in the store will help avoid excessive attention.

Keep Your Budget in Mind

Be sure to know your budget. I am terrible at buying too many clothes, but with time and awareness have been getting better.

Always be on the lookout for a deal. Women’s clothes go through sale cycles faster than men’s. You are far more likely to catch bargains for end-of-season clearances. Items that also haven’t sold many units will be priced significantly lower.

Enjoy the Experience

If the store is particularly friendly, they know they will be able to sell more items. It is in their interest to be nice.

Hopefully, afterward you can take your items back home and enjoy your new clothes. A large part of buying clothes in person is confidence; the more times you do it, the easier it becomes.

Enjoy the new clothes!