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How to dress when you’re overweight

When you’re overweight, it can feel impossible to find clothing that is both fashionable and flattering for your figure. But there are a few easy tips and tricks to keep in mind that can make it easier.

How to dress when you’re overweight
Matilda Davies
· 9 min read

How to dress when you’re overweight: Your questions answered

  • What shoes should I wear if I’m overweight?

    Often, the suggestion for overweight women is to wear high heels to elongate the legs and make you look taller. While this is good advice, it often isn’t practical. But you can still elongate your legs by wearing shoes with a pointed toe (like brogues or mules) or wearing trendy trainers that aren’t overly bulky.

  • Can overweight women wear bright colours?

    Of course! Bright colours can look stylish and elegant on any body shape. To get the ultimate bold-yet-classy look, opt for a monochrome suit in a bright red or emerald green. Take inspiration from older celebrities like Viola Davis or Vanessa Williams, who are a lesson in rocking glam monochrome suits.

  • How do I accessorise if I’m overweight?

    With accessories, similar advice applies to clothing. Avoid overcompensating with large, gaudy accessories to distract. Instead, opt for simple, elegant pieces like a few metal bangles or a long pendant necklace to add some extra glam to your outfit without going over the top.

  • Is black flattering for overweight women?

    We always hear the ‘black is flattering’ mantra and lots of women rely on this. But black can also be a little boring. Just remember that generally, dark colours minimise and light colours maximise. So, if you’re a pear shape (larger on the bottom) or an inverted triangle shape (larger on the top), wear a darker colour where you’re larger and a lighter colour where you’re smaller to even out your proportions.

If you're overweight, it can feel impossible to find clothing that is both fashionable and flattering for your figure. Looking at the models on clothing websites and in fashion magazines who don’t look like you, how can you know if those clothes will look good on your body? But there are a few easy tips and tricks to keep in mind that can make it easier.

As long as you're happy and healthy, being overweight doesn't have to be a bad thing. Embrace your curves and love the body you were given. Whatever your style, there will be something out there that will work to both flatter your body shape and make you feel more you.

So, here are a few things to keep in mind when you’re looking to update your wardrobe, to make sure you’re dressing to make you look and feel your best.

Don’t rely on oversized clothes

Many women who are overweight or have larger frames will try to cover it up. Thousands of wardrobes across the country are filled with clothes that are (at least) two sizes too big for them and have a baggy and shapeless fit. It may seem obvious, but wearing clothes that are too large will only make you look larger. They make you look and feel less confident as well! Confidence is the key to looking great no matter what you wear, and trying to hide yourself is not the path to feeling confident in your body.

Well-fitting clothes will always be in vogue. Unfortunately, as they get older, many women lose track of their size and dress to the size they were ten or twenty years ago. If you're not sure what your size is or you think you may be wearing the wrong size, visit a local personal shopper who can measure you and explain your body type so you can dress to flatter it.

Make friends with your local tailor

Going hand-in-hand with the previous tip is finding a local, quality tailor and making them your best friend. Even if you know your size down to the centimetre, clothes are built for average bodies so that they can be replicated hundreds of times and fit most people. But the truth is: most people don't have the 'average' body. Bodies come in all different shapes and sizes. In addition, people carry their weight in different areas of their bodies and have different proportions. As such, most off-the-rack clothing won't fit perfectly.

That’s where your local tailor comes in. Buying all of your clothes custom-made would be both extraordinarily expensive and time-consuming. It's a far better deal to buy quality clothes and get them altered to fit your body perfectly so they'll last for years. Constantly buying new cheap clothes because things don't fit right or flatter you costs far more in the long run! Ditching fast fashion is much better for the environment, too. Depending on how much something needs altering, a basic tailoring service generally costs between five and fifteen pounds per garment. But it's worth it because then every piece of clothing you own will look like it was made for you. It will fit your body perfectly and be as flattering as it can be.

Wear the right undergarments

People often forget about their undergarments when trying to find a flattering outfit. However, they're more vital than you might think. Thousands (if not millions) of women wear underwear that's the incorrect size. This is particularly true for overweight women who may feel less comfortable getting measured and fitted correctly. Wearing ill-fitting underwear will make you look like you have more lumps and bumps than you actually have, even if you're wearing perfectly fitted clothes over the top. For underwear, take the tip above and go to a local personal shopper to discover your correct size. They don't have to measure you for underwear specifically, but you can buy underwear in the right size once you find out what size you should be wearing.

Bras can be challenging to get right. The sizing is confusing, and many women still don't understand how bra sizing works. The measurement directly under your bust is your band size, rounded to the nearest whole even number. The cup size is your band size subtracted from the measurement around the widest part of your bust (rounded up to the nearest whole number). In cup size, one inch is equivalent to an A cup, two inches is a B cup, and so on. So, if your band size is 38 inches and your bust size is 42 inches, your bra size is 38D. While you can work this out yourself at home, it's best to go into a store and be measured by a professional. While many women don't feel comfortable doing this, remember that this is their job. They have probably seen hundreds of women's bodies of all different shapes and sizes over the years. And ideally, you should get a bra fitting at least once per year because your bra size changes over time more than you think!

Embrace layering

For any body type, layering is a stylish look that can make you look more put together while still flattering your figure. The key is not to make any of the layers too bulky. For example, if you're going for a casual daytime look, like jeans and a fitted top, throw a flowy cardigan or a kimono on over the top. It will make you look like you put in that little bit more effort while also making you feel more comfortable if you're not used to wearing tight or fitted clothing.

In the summer, a kimono, a thin cardigan or an overshirt are the perfect match for most outfits. If you want to dress it up a little, go for a well-fitting blazer. In the winter, layering is a bit easier, and many people do it automatically anyway. A structured wool coat will elevate almost any look and be flattering at the same time. Less structured overcoats, like a trench coat, can also work well, particularly with dresses. Use a belt to sinch in the waist to avoid looking too bulky or hiding your figure.

Don’t overcompensate

Often, women get concerned about what they shouldn’t wear after 50, or if they're overweight, so they overcompensate. This can mean wearing clothes that are too big or too small, wearing loud patterns to distract the eye, or wearing lots of thick makeup to try and cover-up. Instead, if you want to look younger, slimmer and more stylish, look for well-fitting, classic, elegant clothes that will stand the test of time and make you look effortlessly fashionable. Confidence is the best accessory, and overcompensating will only make you look like you’re trying to hide yourself.

We've covered why wearing oversized clothes does nothing for you but wearing clothes that are too small has a similar effect. Everyone has seen a woman in clothing that is blatantly too small for her, and it rarely looks good. It tends to look like you're still wearing clothes that you outgrew years ago, and you're in denial about it. Well-fitting clothes are vital to looking your best at any weight. Patterns can be chic and beautiful if done right, but some overweight women find loud, gaudy prints as a way to distract from the body underneath. This is another classic overcompensation. Instead, go for a simple, understated pattern like a simple floral or vertical stripe. This will keep you looking classy and flatter your figure without looking like you’re overcompensating.

Think about the cut

Often, the cut of clothing isn’t something people think about when they get dressed, but it can easily make you look larger than you are, so it's worth paying attention to. The main thing to think about with the cut of clothing is where the clothing ends. Ideally, you don't want clothing to end on the larger sections of your body because it will highlight them and make them look wider. For example, a jacket that ends at the broadest part of your hips will make your hips look wider while covering up the skinnier parts of your body. So either look for a jacket that ends higher, like a cropped jacket that ends on or just below your waist, or a longer jacket that will elongate your figure.

This can be a great thing to use your tailor for. Unfortunately, clothing brands often aren't very good at making clothing that works for different heights, so it can mean clothes cut off in the worst place possible. But that doesn't mean you have to throw out all your favourite tops and jackets. Instead, visit your tailor and see if they can lift the hem a little, so the garment cuts off slightly above the widest part. This minor adjustment will work wonders in making your wardrobe as flattering as possible.

Pay attention to what makes you feel comfortable

As we've mentioned, the number one rule of looking great is feeling confident. Feeling yourself and feeling comfortable in what you're wearing will make you exude style and grace. Confidence can even improve your posture! Not feeling good about yourself and your body often makes people hunch their shoulders and slouch in an unconscious attempt to make themselves look smaller and avoid being seen. But slouching gives the appearance of dreaded rolls in women of most sizes. Instead, stand up straight, roll your shoulders back, and walk with confidence.

Even when you’re adhering to all of the other tips and tricks on the internet, not everything will make you feel confident in yourself. Everyone has different styles that make them feel good, and that's completely normal. So when you find yourself in an outfit that makes you feel like your best self, take a mental note of what you're wearing so you can replicate the outfit (and the feeling) later and find similar clothing that makes you feel your best.

Matilda Davies
Matilda Davies
Matilda is an experienced journalist and content creator who has written for local, national and global publications. She is passionate about culture and lifestyle content, and connecting with audiences through these topics.