Bra Fitting 101

Posted by Anna Reid on

"I don't think my bra is fitting me very well"

"I have no idea what size I should be wearing"

"Can you help me find a bra that fits??" 

These are some of the most common things we hear at The Cherry Tree Boutique! Read on if you'd like to learn how to find your size, and how to troubleshoot some common fitting problems. 

Figuring Out Your Bra Size

The main thing you'll need to determine your bra size is to take two measurements: your band, and your cup. You may find it easier to have someone else help you measure. Measure yourself while wearing an unpadded bra (but preferably not a sports bra), and either a thin shirt, or no shirt at all. Stand tall with proper posture, and hold your arms out to the side.

To measure your band, wrap the tape measure around your ribcage, just under your breasts, where the band of your bra is sitting. The tape measure should be parallel to the floor, which may mean it doesn't follow the band of your bra all the way around. The tape should be flat against your skin, but not tightened or super snug. The number you get, in inches, is your band size. Let's use 36 as an example. 

To measure your cup, use essentially the same process, but measure around the fullest part of your breast. Many women find the measurement goes right across their nipple, but this isn't always the case. Again, the tape measure should be against your body, but not pulled too tight. The measurement in inches, helps determine your cup size. Let's use 44 as an example.

To calculate your cup size, you need to calculate the difference between your band and your bust. Each cup size is equal to 1-2 inches, depending on the brand of bra. The cup sizes go up in alphabetical order as follows: A, B, C, D, DD, E, F, FF, G, GG, H, HH, J, JJ, and so on. 

So, in the example above, of a 36-inch band, and a 44-inch bust, the cup size would fall anywhere from a D to a FF, depending on the brand. Commonly, European brands are sized smaller in the cup than American brands. This person might wear a 36D in an Olga bra, for example, but a 36FF in an Elomi. 

The Perfect Fitting Bra

So, how to tell when your bra fits correctly? The band should always be on the LOOSEST hook-and-eye setting when trying a new bra, and should be nice and snug. The reason for this is as you wear the bra, it will stretch, and you need to then be able to tighten it. The band should not be so tight that it is painful or uncomfortable, but should still be quite snug. The most common fitting mistake we see is women wearing a band size that is too large. The majority of the support in a bra comes from the band and cup structure, so especially for those with larger breasts, it is very important that your band is tight enough, and it may need to be tighter than you expect. Your shoulders will thank you!!

The front of the bra, where the wires meet (if it's a wired bra) should be laying flat against your breastbone. If not, you may need a larger cup size. 

There should be few-to-no wrinkles or gaping/space in the cup fabric, and your breast tissue should not be spilling out the top or sides. 

For those with unevenly sized breasts, we always recommend fitting to accommodate the larger side.


Here we will discuss a few of the common fitting issues and how to solve them!

Band Riding Up

This is a very common problem to have. Fortunately, it has a simple solution! If your bra band keeps migrating up your back, it means your band size is too big. Your upper back is wider than your mid-back, so if your bra band is correctly sized to your mid-back, it won't be able to crawl its way up. 

Breasts Falling Out the Bottom of Your Bra

It's no fun having to stop an activity or task because you've got an underwire sitting straight across your nipple! This is essentially the same problem as above, but happening in the front instead of the back. If you find your breasts are prone to slipping out the bottom of your bra, this is a sign your band is too big. 

Straps Digging In

This is another telltale sign that your band is too big. As mentioned above, the majority of the support in a bra should come from the band and cup, leaving just a little bit of stabilization to be done by the straps. If your straps are digging in, this means too much of the weight of your breasts is being put on your straps, and not enough support is coming from your band and cup. This can be fixed by - you guessed it - moving to a smaller band size. 

Straps Sliding Off Shoulders

This one is also very common. If your band fits correctly, it could simply mean that your straps need to be tightened. However, if you have a narrow frame making your straps prone to sliding down your shoulders, you could benefit from wearing what is referred to as a "U-Back" bra. This simply means the straps are set fairly close together in the back, and they form the shape of a "U" with the band of your bra, rather than looking like the upper half of a capital "H". You may also want to try racerback, or criss-cross styles. At The Cherry Tree Boutique, we do sell converters for $2 which can convert any bra straps into a racerback!

(Pictured below is the Elomi "Kim" bra, an example of the U-back style mentioned)

Breasts Spilling Out Top of Cup, AKA "Quadboob"

If you find the top of your cup forms an indent in your breast tissue, making it look like you've got a boob on top of your boob, not to worry! This simply means you need to increase your cup size. 

Breasts Spilling Out Sides of Cup, AKA "Sideboob"

Sideboob is a thorn in the side of MANY women. Sometimes, it seems no matter how much you adjust your band or cup size, you've still got that pesky underarm bulge that will not go away. The tendency is to increase band size to make the bulge less pronounced, but this truly will not solve the problem (unless your band is WAY too tight) and will simply offer you less support. 

A couple notes about sideboob before we talk about solving it. First off, women of all, and I mean ALL, shapes and sizes struggle with it. It is natural to have some fat in our underarm area. Some of what we see as "fat" is also simply the relaxed muscles that allow us to put our arms over our heads! Second, I promise you that you notice it more on yourself than anyone else does. Think about it - how often do you notice another person's underarm fat? How often do you notice your own? 

With all that said, there are a few ways to minimize it. Occasionally, going up a cup size will help. Often times, transitioning from a molded cup to a cut-and-sewn style will offer a smoothing effect on the sides. This is because the cups conform to your shape, more so than your breasts having to conform to the shape of the bra. Another trick is to try to find a bra with side support pieces. We do have several of these available at the Boutique, and any of our staff would be happy to help you with them. 

Underwires Causing Pain

A correctly fitting bra should NEVER hurt you. Sometimes, a brand new bra can take a couple of wears to really feel like it's "broken in", but even during that period, it should never be painful. A good-quality, correctly-fit underwire should not poke, dig in, or rub you. Before giving up on underwires completely, it can be worthwhile to come in for a fitting, and perhaps try on a couple of brands you've never tried before. 

Having said that, some women just do not like the feeling of an underwire, and that's okay too! This is especially common in women who have had an injury to their ribs or torso, or breast cancer survivors. We have many options of wire-free bras and are more than happy to help you find one that meets your needs. 


Hopefully this has shed a little light on the world of bra fitting! Fittings are always free at The Cherry Tree Boutique, and any of our knowledgeable staff would be happy to help you find your perfect fit. Thanks for reading!


- Anna

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