Beginner Crossdressing Tips

We estimate that 30 to 40% of all visits to our retail showroom in Fairfield, NJ are from relative ‘novices’ who have dressed sporadically during their lifetime (possibly from childhood) and come to us because they reach a stage in their life when they want the lifestyle to become a more regular happening. For many this will mean dressing on their own and in private with no wish to go out in public. They may take pictures and share online and interact with other crossdressers or even admirers but for the most part they dress in private and want to keep the lifestyle separate and indeed hidden from their regular ‘male’ life.

For those starting out on this journey of discovery and delight we include some basic tips for the beginning crossdresser with a particular emphasis on easy and inexpensive solutions. We know many clients who can only experience the wonder of dressing up a few times a year so it’s important they know how to put together an outfit quickly since time is often of a premium.

For Volume 1 on this subject we will concentrate on:

  • Basic Shaping Garments
  • Dresses v Skirts and Tops
  • Undergarments and Hosiery
  • Shoes

For beginners to crossdressing it’s important to concentrate on easy and cost-effective purchases at the outset of your femme adventure to ensure you have a pleasurable experience. With that in mind all the recommendations we give are based on experience of what will work for most body-types.

BASIC SHAPING GARMENTS: Most body-types require some shaping to emulate a female shape; it doesn’t matter if you are lean or a fuller body-type you will need one or more of the following items to get you started:

Breast Forms: Breast forms do 3 things for the male shape: first of all they make all ladies clothing fit and look much more attractive. Secondly, they help soften the look of wide male shoulders and thirdly, breast forms just automatically make you look and importantly feel more feminine. Unless you have a thing for large breasts then start with a C or B cup so you are proportional. Also, if you go too large you’ll have issues finding ladies clothes that fit. If you can, buy silicone forms since they are the closest to looking and feeling like the real thing. You can spend hundreds of dollars on these but to begin with look for sale items like the Wider Full Teardrop Breast Forms from that cost from just $19.95 a pair and can be used with regular bras or even adhesives.


Corsets/Cinchers/Slimmers/Girdles: Moving on down the body part of creating an ideal female silhouette is to strive for an approximation of an hourglass figure; that is a waist slimmer than the chest and the hips. This gets more difficult for most with age but there are quick solutions. If you only need to smooth the waist area and lose just an inch then a simple rubberized slimmer or girdle will help. If you need to lose 2 to 5″ then you need a steel boned corset. These take more time to fit when dressing but they are the only garment that can radically reduce the waist area to get the female shape you want. You can buy rubberized cinchers from $10 or an Affordable Steel Boned Corset for just $49.95.

Hip Padding and Padded Panties: As a male you will most likely have very little natural female hip action going on and so need to add here. There are some realistic silicone options now available running in the hundreds of dollars but we want simple and cost-effective here so go for either stand-alone foam pads held in place by good quality pantyhose or a good quality pair of padded panties like the Padded Rear and Hip Shaping Girdle which contours nicely for a natural fem-shape and just needs to be pulled on an off. It also costs less than $50 so is very reasonable.

DRESSES VERSUS SKIRTS AND TOPS: You’ve figured out your foundation garments that will give you an approximation of a female hourglass figure shape and now you want a simple outfit or two that you can dress up. As a beginner remember some of the basics wherever you clothes shop. Male bodies have different proportions: wider shoulders, longer torsos, slimmer hips etc. If you are particularly athletic with a triangle shape body then unless you pad up in the hip area you will definitely want to shop for skirts and tops where you can but bigger tops but a smaller skirt to fit your body-type. Many like to dress in skirts and tops because you can mix and match outfits to great effect. On the other hand dresses are simple and sexy if you get the right shape. For most beginners where shaving the body is not an option then dresses like our basic Little Black Dress for Crossdressers is an ideal solution. It’s sexy, stylish, cut with wider shoulders and longer torso and full length sleeves and high neck to mask hair. If you feel brave enough to venture out to shop at consignment stores or even chain stores just make sure to choose garments with some spandex/lycra in so they will stretch in areas like the shoulder – 100% cotton or polyester will not work for most.

UNDERGARMENTS AND HOSIERY: Most novice dressers we meet cannot suddenly start shaving all over the body as friends and family would notice which could lead to awkward questions. Long sleeve, high-neck dresses will take care of the upper body but for legs some good quality Opaque (full cover) Pantyhose, stockings or stay-ups will not only shape the legs but mask all hair and blemishes. The other essential for a beginner would be a Crossdressing Gaff for tucking the ‘boys’ to get a nice flat front on your dress or skirt. If you don’t use a tucking gaff then you can do the same with multiple pairs of control top pantyhose but that can become hot!

SHOES: Just about everyone we meet wants a pair of high heels and many novices will start out aiming for a 4 or even 5″ shoe. We always say that unless you are well practiced then do your feet and back a favor and start out with a 3″ heel shoe that’s easy to walk in like the Divine Ladies Pump. For sizing the easy rule of thumb to remember is you add 2 full sizes to your male shoe size for closed toe styles and add 1.5 full sizes to your male shoe size for open toe styles. If in doubt call us at and we’ll make sure you get the right size. If you simply can’t help yourself and feel you must have a 4 or 5″ heel then make sure it has a platforms sole which is much easier to walk in. Other good recommendations for novice dressers are pumps with ankle straps for added security, plain T-strap sandals for the same reason or even ankle boots which give great support. Remember, keep it simple and start out conservatively; you can always get bigger heels once you have practiced. Choose a neutral color like Black with your first pair so it will match with your first outfit. If you start dressing more and buy more outfits then you can think about shoes with color later on.


For beginner crossdressers the number one tip is to buy effective, affordable and simple solutions. If you only dress occasionally then buy good affordable everyday items like the examples above at and take care of them. Store correctly and you will have for many years to come. If not sure where to start then read the articles in our Crossdressing Tips section and follow up with us with any questions to make sure you get the right garments in the right size first time around.