dress well while losing weight

How To Dress Well While Losing Weight and Look Ultra Stylish While You’re In-Between Sizes

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I’m sure everyone can agree that a weight-loss journey is no easy feat. Not only is there sticking to a new diet and finding the motivation to go to the gym consistently, but then there’s also adjusting your entire wardrobe as you slowly but surely drop a few inches. If trying to transition your wardrobe to your weight loss journey has been a headache, here you’ll find some helpful tips to show you how to dress well while losing weight. Because feeling good in your clothes shouldn’t be something you can only feel when you hit a certain size. It can happen now!

1. Invest in Clothing Items With Stretch Fabrics

Stretch fabrics will be your new best friend throughout your weight loss journey. This customizable fabric can adjust to your body no matter what the scale says. Basic pieces like jackets, bottoms, sweaters, and shirts in a stretchy knit, spandex, or cotton material can look great on your fluctuating body weight.

Stretch denim is also another perfect investment piece you need in your transitional wardrobe. Avoid rigid denim and look for jeans that have some stretch in the legs and thighs, as these will fit your fluctuating body the best.

If you are worried that you’ll waste money if you buy skirts and pants as you continue to lose weight, look for pieces with an elastic waist to help you on your weight loss journey. This is a must-have feature as they will transition with your body shape, being a piece you can wear now and later.

Denim jeans with an elastic waist can look cool, but proceed with caution as this style can easily look frumpy and outdated. Features like a drawstring waist or jogger silhouette style can make this look more intentional and even cool.

 2. Go for a Monochromatic Look

This is another important tip to know when learning how to dress well while losing weight. Solid colors like black, midnight blue, and plum have proven to be a great way of creating a slim and elegant look. There’s a reason why it’s the oldest trick in the book!

When you are building your new figure, you can dress up in a monochromatic look to create the illusion of a smaller figure before you reach your weight goal.

Related: Wondering What Colors Make You Look Skinny? Read This Post!

3. Wear Mid Rise Jeans

A struggle many women face is finding a new pair of jeans that can adapt to their bodies as they lose weight. It’s either the jeans end up being baggy, especially around the waist, or too small to squeeze in. However, mid-rise jeans are a good pair of jeans to wear during your weight loss journey.

They are universally flattering jeans that you can use on rotation. And since they are versatile, your styling options are endless. For casual days, wear them up with a tank top, sneakers, and cardigan. To dress them up, pair them with block heels and a statement blouse.

And if you are still trying to get a smaller stomach, the mid-rise jeans will act as a tummy control while you lose weight.

4. Accessorize Your Casual Looks 

“These sweatpants are all that fit me right now.” Name that movie!

Sometimes the only things that will fit you are your sweatpants, leggings, t-shirts, and joggers. And though you may feel as if they’re not your most stylish pieces, the good news is that you can dress them up as needed.

The secret to dressing up your casual looks is with accessories. No fashionable outfit is complete without them- including sweatpants! Accessories are always a good thing to purchase during your weight loss journey to jazz up your looks because they will be something you can wear now and when you reach your goal weight.

You can use accessories to dress well as your body size reduces. Elevate your t-shirt and jeans outfit with a scarf or an elegant brooch. Putting on some chic sunglasses with your baseball cap and joggers portrays a look that is casual chic. Layered necklaces can make even the most basic t-shirt look more stylish. Sunglasses, purses, and jewelry can finish off your look so effortlessly.

And don’t forget your shoes. A pair of good shoes can act as the perfect accessory to wear on your weight loss journey. Practical and stylish footwear like ballet flats and loafers will round off your looks perfectly.

5. Consider Shapewear

Wearing shapewear can make you feel more confident while you’re working to achieve your goal weight. Shapewear can give your outfit a seamless look by smoothening and lightly re-shaping your silhouette.

Whether it’s a special event or another day at the office, you will feel more confident wearing your tops and wedding guest dresses. And thankfully, shapewear has come a long way, so you can find inclusive sizes and shapewear in many different tones to match your skin shade.

6. Use Anson Belts

anson belt

Anson belts are not like ordinary belts. They have a “ratchet-style” system that’s hole-less, meaning you have the flexibility to adjust the belt throughout your weight loss without the limitation of holes.

If you find regular belts frustrating and you’re someone that’s always between sizes, one of the keys to dressing well while losing weight is to use an Anson belt for your pants or to cinch in your dresses and trench coats.

At first glance, they may look like they are primarily for men, but a simple leather belt can look great on anyone. Plus, they have stylish women’s options too.

7. Tailor Clothes As Your Body Changes

If you frequently read about ways you can dress better, then you probably read all the time about how you should tailor your clothes. And if you’re like me, then you usually dismiss this idea thinking it’s only for “hoity-toity” people. But in the right situation, it can actually be a good idea!

Sometimes it’s actually cheaper to alter and tailor your clothes than it is to buy new. Not to mention more sustainable. Depending on the fix, alterations range from $15-$75.

If you’re doing something simple like taking a shirt in or slimming the sleeves because you lost weight, then it makes more sense to simply alter what you have instead of starting over as the right tailor can adjust it to give you the right size for your body type.

On your weight loss journey, you can spend $15 to alter a shirt to your current size and the end result is a polished outfit and pulled-together look.

8. Keep Clothes That Fit Your Current Size

As mentioned earlier, you don’t have a whole new wardrobe whenever your weight changes! Instead, search your wardrobe to find clothing pieces that can look great on you while you lose weight.

Do a closet audit to make finding these items easier. Create three piles of clothes: Keep, donate, or alter. The clothes you keep are the ones that fit you now and you look good in them. You donate the clothes that don’t fit you now and you don’t like them enough to alter or make them work later.

Just make sure that you hold on to clothes that are classic, whether that be basic t-shirts or lightweight sweaters, as these clothing items can be worn all year round and for different occasions too.

And then once you’ve audited your wardrobe, do simple styling tweaks to make these existing pieces of yours feel new and exciting again. Related: 20+ Style Tips That Will Instantly Make You Look More Fashionable

9. Stock Up on Dresses (Especially Wrap Dresses)

Sometimes all you need is one gorgeous dress to have you look amazing while you lose weight. Forgiving silhouettes like a tie-waist shirtdress, babydoll, tiered, and a-line are all good ideas, but a wrap dress is a wardrobe must-have.

The best part about wearing wrap dresses when you want to dress well while losing weight is the tie feature. It is very useful if you need to adjust the size several dress sizes, as you can tighten or loosen the dress as your body fluctuates. Whether you have a wedding to attend or just want to look nice for your day-to-day, get a wrap dress that will fit you now and in the coming months.

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When you are trying to achieve your weight loss goals while maintaining a stylish wardrobe for your new size, there are many factors to consider, including your age and lifestyle. But these 9 tips will work for everyone and have you looking stylish in the in-between!

For more weight styling tips, follow these fashion hacks for mature plus-size women.

Up next: 10 Fashion Hacks for Plus Size Ladies Over 50

how to dress well while losing weight
how to dress well while losing weight


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making mychicobsession.com a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys, her biggest fashion critics.