Buying women's underwear becomes much easier once you know your measurements. Guessing your size often leads to underwear that digs into your waist, rides up, feels loose in the wrong places or simply doesn't give you the comfort you're looking for. A few minutes with a tape measure can save disappointment, money and repeated returns.
Many crossdressers also assume they need to buy much larger sizes simply because they were assigned male at birth. While body shape certainly affects fit, women's underwear is designed around body measurements, not gender. Knowing your waist and hip measurements gives you a far better starting point than choosing a size based purely on instinct.
After running ClubCrossDressing since 2009, we've seen countless members become frustrated because they bought beautiful lingerie that simply didn't fit properly. In most cases, the problem wasn't the underwear. It was starting with the wrong measurements.
This guide explains exactly how to measure yourself, how women's underwear sizing works, and how to choose styles that feel comfortable and flattering. If you're completely new to feminine clothing, you may also find our complete guide to crossdressing a helpful place to begin.
Why measuring yourself matters
Unlike men's underwear, women's sizing varies considerably between brands. A size 14 in one retailer may fit almost identically to a size 16 somewhere else. Some lingerie brands even use dress sizing, while others use Small, Medium and Large.
Because of this, experienced shoppers rarely rely on the label alone. Instead, they compare their body measurements with the manufacturer's size guide before placing an order.
This is especially important when shopping online, where you cannot try items on before buying them. A proper set of measurements gives you confidence that you're choosing the closest available size.
What you'll need
You don't need any specialist equipment.
- A flexible fabric measuring tape.
- A mirror if possible.
- Something to record your measurements.
- Light clothing or underwear while measuring.
Avoid measuring over bulky clothing, as this can easily add a centimetre or two and affect your results.
Which measurements do you need?
For almost every style of women's underwear, only two measurements are essential:
- Natural waist.
- Full hips.
Some shapewear manufacturers also ask for your high hip measurement, but for everyday briefs, bikinis, hipsters and thongs, waist and hips are normally enough.
If you're shopping for bras at the same time, don't confuse underwear sizing with bra sizing. Bras require completely different measurements. Our guide on how to choose your first bra explains that process in detail.
How to measure your natural waist
Your natural waist is usually the narrowest part of your torso. It sits above your hips and below your ribcage.
- Stand naturally without sucking your stomach in.
- Relax your breathing.
- Wrap the measuring tape around your waist.
- Keep the tape level all the way around.
- Pull it snug but not tight.
If you're unsure where your natural waist is, bend gently to one side. The point where your body naturally creases is usually your waistline.
Write the measurement down in both centimetres and inches if possible. Different retailers use different units.
How to measure your hips correctly
Your hip measurement is usually the most important number when buying women's underwear.
Wrap the tape around the fullest part of your hips and buttocks. This is often lower than many people expect. Check in a mirror that the tape remains level all the way around.
Don't pull the tape tight enough to compress your body. It should sit comfortably against your skin without squeezing.
Many beginners accidentally measure too high around their hips, which results in buying underwear that's too small.
Should you measure while tucked?
Usually, no.
If you're buying everyday underwear, measure your body in its natural state. This gives the most consistent sizing across different styles.
If you're specifically buying underwear designed to be worn while tucked, you may want to take an additional measurement after tucking so you can compare the difference. However, always use the retailer's own sizing guide if they provide advice for tucking garments.
Comfort should always come before achieving a particular appearance.
Understanding women's underwear size charts
Once you have your measurements, compare them with each retailer's size guide rather than assuming you'll always wear the same size.
For example, you may discover:
- Your waist suggests a Large.
- Your hips suggest an Extra Large.
In that situation, it's usually better to buy for your hip measurement, especially with briefs and bikini styles. Fabric can comfortably accommodate a slightly looser waist far more easily than underwear that's too tight around the hips.
Stretch fabrics can offer some flexibility, but relying on stretch alone often results in uncomfortable underwear.
How different styles affect sizing
Not every style fits in exactly the same way.
Briefs
Traditional briefs provide the greatest coverage and are usually the most forgiving if you're between sizes.
Bikini briefs
Bikinis generally sit lower on the waist, so checking both waist and hip measurements becomes more important.
Hipsters
Hipsters sit lower still and rely more heavily on hip measurements than waist measurements.
Thongs
Because they use less fabric, accurate hip sizing becomes particularly important. A thong that's too small can quickly become uncomfortable.
High-waisted briefs
These usually benefit from accurate waist measurements, particularly if you're looking for gentle shaping or a smoother silhouette.
If you're building your first feminine wardrobe, our guide to crossdresser wardrobe essentials can help you decide which styles are worth buying first.
Should you size up?
One of the most common questions we hear is whether crossdressers should automatically buy a larger size.
The answer is no.
Your body proportions may differ from the average woman, particularly around the waist and hips, but that's exactly why measurements matter more than labels. Many members are surprised to discover they actually wear smaller sizes than they expected, while others need larger sizes because of hip or waist measurements rather than simply because they're male.
Ignore assumptions and trust the tape measure instead.
Body shape matters just as much as measurements
Measurements tell you which size to begin with, but body shape influences which styles feel best.
For example, someone with broader shoulders and narrower hips may prefer fuller briefs that visually balance their proportions. Someone with a fuller lower body may find bikini briefs or hipsters particularly flattering.
If you're still developing your style, our guides on choosing flattering fabrics and fits and developing your personal style explore this in much more detail.
Common measuring mistakes
Most sizing problems come from simple measuring errors rather than unusual body shapes. Taking an extra minute to check your measurements can make a noticeable difference.
The most common mistakes include:
- Measuring over thick clothing.
- Pulling the tape measure too tightly.
- Letting the tape slope upwards or downwards instead of staying level.
- Holding your stomach in while measuring.
- Using old measurements after gaining or losing weight.
If your measurements fall between two sizes, don't assume the smaller one will stretch enough. Look at the fabric composition and read any sizing advice provided by the retailer. Cotton underwear often has less stretch than microfibre or fabrics containing elastane.
How often should you remeasure yourself?
You don't need to measure yourself every time you shop, but it's worth checking every few months or whenever your body changes noticeably.
Weight changes, fitness routines and ageing can all affect your waist and hip measurements. Even relatively small changes can move you into a different size with some brands.
Keeping your measurements written down in your phone makes online shopping much quicker.
What if you're between two sizes?
This is extremely common.
If one measurement falls into one size and another falls into the next size up, think about the style you're buying.
- Stretchy everyday briefs usually allow a little flexibility.
- Structured lingerie generally fits better when you size for your largest measurement.
- Shapewear should follow the manufacturer's chart rather than sizing down in the hope of creating more shaping.
Buying underwear that's too small rarely produces a smoother appearance. Instead, it often creates visible lines and feels uncomfortable after only a short time.
Choosing underwear that feels feminine
Once you've found the correct size, the next decision is choosing styles that match how you want to feel.
Some members enjoy practical everyday underwear in soft cotton or modal fabrics. Others prefer lace, satin or silk because those fabrics make dressing feel more special. There isn't a right or wrong choice.
If you're only just starting to explore feminine clothing, you don't need an entire drawer full of elaborate lingerie. A handful of comfortable, well-fitting pieces often gives you far more confidence than buying lots of items that don't quite fit.
Our guides to building a lingerie drawer and choosing lingerie that feels feminine can help once you've found your size.
Buying underwear discreetly
Many people take their first measurements because they're planning to buy underwear online rather than in a shop.
Shopping online gives you time to compare measurements, read reviews and choose styles without feeling rushed. Most retailers also publish detailed size guides, making accurate measurements even more valuable.
If privacy is important to you, our articles on discreet crossdressing shopping and managing your privacy while crossdressing include practical advice on deliveries, storage and keeping purchases private where necessary.
Building confidence through clothing
Finding underwear that fits properly isn't just about comfort. For many crossdressers, it's one of the first steps towards feeling more authentic and relaxed when presenting femininely.
Ill-fitting clothing can become a constant distraction. Well-fitting underwear, on the other hand, quickly disappears into the background, allowing you to focus on enjoying the experience rather than adjusting your clothes.
As your confidence grows, you'll naturally discover which cuts, fabrics and brands suit both your body and your personal style.
If confidence is something you're actively working on, our Crossdresser Confidence Guide explores practical ways to become more comfortable expressing yourself, whether you dress privately or hope to venture out in public one day.
Can you ask for help?
Absolutely.
Many members of ClubCrossDressing remember how confusing sizing felt when they first started. Sharing measurements isn't necessary, but discussing brands, styles and fit can save a great deal of trial and error.
Joining conversations with people who have already tried different underwear brands often provides advice that size charts alone cannot. It's also reassuring to discover that almost everyone has ordered the wrong size at least once.
One of the biggest benefits of being part of a supportive community is learning from other people's experience instead of having to work everything out on your own.
Frequently Asked Questions
Should crossdressers use men's or women's measurements when buying underwear?
Use your own body measurements. Women's underwear is sized using waist and hip measurements, regardless of who is wearing it.
Can I use my men's trouser size?
Not reliably. Trouser sizes vary between manufacturers and don't account for hip measurements, which are often the most important measurement for women's underwear.
Is it better to buy a larger size for comfort?
Not necessarily. Buying too large can cause underwear to bunch, twist or lose support. Following the retailer's measurement guide usually gives the best result.
Do different brands fit differently?
Yes. That's why you should compare your measurements against each brand's own size chart instead of assuming you'll always wear the same size.
Can I measure myself without help?
Yes. A flexible tape measure and a mirror are usually all you need. Measuring twice helps confirm you've recorded accurate numbers.
Recommended Related Reading
Meta Title
How to Measure Yourself for Women's Underwear | ClubCrossDressing
Meta Description
Learn how to measure yourself for women's underwear with confidence. Discover accurate waist and hip measurements, sizing tips and common mistakes to avoid.
Category
Crossdressing Advice & Tips
Suggested Image
A neatly laid out soft tape measure beside folded women's underwear in several styles, including briefs, bikini briefs and hipsters, on a clean dressing table. The image should feel welcoming, practical and discreet, with no explicit content or visible models.
Explore More Crossdressing Articles
Looking for more advice, stories and updates? Browse our complete collection of crossdressing articles.
Browse All Crossdressing Articles
Looking for In-Depth Guides?
Prefer more detailed advice? Visit our Crossdressing Guides Hub for practical guides covering confidence, clothing, makeup, relationships and community support.


ClubCrossDressing ®



























