Take all your body measurements. Before shopping for clothes, you have to know all your measurements. The 4 locations you have to measure are your chest, bust, waist, and hips. Use a cloth tape measure and wrap it around these 4 areas to get your measurements. Write them all down so you have this information while shopping for clothes.[1] X Research source Keep the tape straight and parallel with the ground while taking measurements. If you plan on wearing a bra, you should measure your bust with the bra on and stuffed the same way you plan on wearing it. There are many techniques for stuffing your bra to the size you want. This is much easier if you have someone around to help you. Find an open-minded friend to assist. If you’re a member of a cross-dressing support group or have made friends in the community, try asking one of them. Measure the distance from your hips to your knees. This is important if you plan on wearing skirts or dresses. Hold the measuring tape at your hip and extend it down to your knee. Note the measurement at the top of your kneecap.[2] X Research source A simple method for taking this measurement is kneeling on the floor so you can reach your knees more

easily. Skirts and dresses usually rest just above the knee, so subtract 1–2 inches (2.5–5.1 cm) to get a good skirt length. Subtract even more if you want a shorter skirt. Plan on covering your more masculine features. All men have different body types, and some features look more masculine than others. Examine your body and see what looks particularly masculine. If you want to pass as a woman, you should plan an outfit that covers or masks these features.[3] X Research source For example, if you have particularly big arms, this might make your crossdressing persona look more like a man. Plan on wearing sleeved dresses or long-sleeved shirts to cover these more masculine features. Ask female friends for their opinions. If you’ve shared your crossdressing plans with female friends, they can be a big help in finding the right look for you. Ask their opinions on what clothes they think would look good on you and take their advice.[4] X Research source If you have female friends who are willing to come along, bring them to the store with you for help picking out and trying on clothes. Shopping with a partner will make you less self-conscious. Advice from fellow crossdressing men

is valuable as well, because they’ve been through the process before. If you have friends or know of anyone who cross dresses, ask them for advice too. If you don’t know anyone personally, there are many internet sites and message boards where cross dressing men share advice and suggestions. Examine how women dress in different situations if you plan on going outside. Some men prefer to cross dress at home with no one around, but others want to go out in public and pass as a woman. If this is the case for you, observe how women typically dress in different places. Then try to adjust your outfits to these situations.[5] X Research source Think about the places you’ll go when crossdressing. Will you just be going out to the store, or will you be visiting a nightclub? You would dress very differently for these occasions. Keep your outfit appropriate to the situation to avoid being recognized. Start out by shopping for clothes online. When you’re first starting out, you’ll probably be shy about entering a store and trying on women’s clothes. Luckily online shopping is a great, anonymous way to start finding clothes. Look on retail sites for clothes that interest you and

order some outfits to get started crossdressing.[6] X Research source Some sites allow you to plug in your measurements and the website will automatically find the right size for you. Utilize this tool if a website has it because you may be a different size at different stores. As an added bonus, many websites allow free returns, so you can make mistakes early on while you find the right clothes and sizes. There are also websites that specialize in products for crossdressing. Check these out for women’s clothes designed for men to wear. Look for shoes that are 1 or 2 sizes larger than your male shoe size. Shoes can be difficult to find for crossdressing men because their feet are bigger than most women’s. It will take some trial and error, but a general rule is to add 1 or 2 sizes to your normal male shoe size to find the corresponding female size.[7] X Research source Adjust this guide if you have to. For example, if you’re normally a size 9 but a women’s size 11 is too big, try a size 10. Buy shoes that you’re comfortable in. If you’ve never worn high heels before, 6 in (15 cm) heels are impractical. Start with a smaller heel, about 2–3 in (5.1–7.6 cm) at most.

Then, if you find these comfortable and get used to walking in them, you can try higher heels. If you want a boost that's easier to walk in than high heels, try platformed shoes. These give you a similar effect without the trouble walking. Buy pantyhose if you don’t plan on shaving your legs. Shaving your legs may make others suspicious if you’re trying to keep your crossdressing a secret. You can hide your leg hair with pantyhose. These will cover your masculine-looking legs without the need for shaving or waxing.[8] X Research source Some websites have a pantyhose sizing chart that will help you find the right size. If you’re between two sizes, go for the larger size to you know they’ll fit. Pantyhose come in many styles and colors. Start by shopping around online for a look that appeals to you and the look you’re going for. You could also wear stockings for a more comfortable option. These only cover your legs and don’t extend all the way up to your waist. Consider a wig to complete your look. A wig will complete your transformation. These are specialty items that you can’t find in most retail stores, so find a special wig retailer. These are items you probably

shouldn’t buy online, because trying on a wig and seeing how it goes with your outfit will help you select the right one. Take your outfits into account to plan on which wig you want.[9] X Research source Try finding a wig store that specializes in crossdressing or drag attire. Employees here will know exactly how to work with you and help you find the right wig. If you’re shy about going to a regular wig store, try telling employees there that you’re planning a costume and need a wig for it. This way you can avoid any stigma that comes along with crossdressing. If you want to pass as a woman, don’t skimp on the wig. A cheap version is fine if you’re only dressing up at home, but a low-quality wig will look very obvious in public. Return anything that you don’t like after trying it on. Finding the right clothes is a trial and error process in the beginning. You’ll make mistakes like buying the wrong size or getting an outfit that doesn’t match the look you’re going for. Don’t hesitate to return any of these items and try again. After a few tries, you’ll have a lot more success finding the right clothes for you.[10] X Research source Bring a woman with you to

shop at the store. You may feel uncomfortable as a man buying women’s clothes in public. If you bring a woman with you, people will probably either assume that she is buying the clothes for herself or as a gift for someone else. This is especially helpful if you haven’t come out to friends or family as someone who cross-dresses and want to keep it a secret.[11] X Research source If you have crossdressing or male-to-female transgender friends, bringing them along can be a huge confidence boost. They’ve gone through the same things you’re going through now and can help give you support when shopping for the first time. Shopping with friends is also important for safety reasons. You can avoid being accosted or harassed if you’re in group. Shop at a thrift store to avoid being recognized. Many crossdressers prefer doing their shopping at thrift stores because people they know are less likely to shop there. This way, they can shop in peace without worrying about someone seeing them.[12] X Research source Try shopping during an off-peak time to further reduce the chances you’ll encounter someone you know. Weekday mornings are usually quiet in most retail stores. Stay calm and

courteous with all store employees. You will probably receive a few strange looks while shopping for women’s clothes, especially if you’re trying them on. Try and ignore these reactions unless someone confronts you. For the most part, store employees will probably treat you like any other customer. As long as you are polite and courteous, employees should treat you with respect.[13] X Research source If you do experience a rude employee, consider leaving that store and shopping somewhere else. No need to give that store your business if you were treated badly.