common fashion struggles for women over 50 and how to overcome them

Can You Relate? 13 Common Fashion Struggles for Women Over 50 and How To Overcome Them

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Do you ever feel like fashion is just not designed for women over 50? You are not alone! In a world where fashion is mainly geared towards younger people, it’s easy to feel as if your struggles don’t matter – or maybe as if they’re all in your head. But I’m here to tell you that many women in this age group experience common fashion struggles such as shopping on a retirement budget, balancing trends without looking like you’re trying too hard to be young, or on the flipside, finding the right clothes so you don’t look too matronly. While these problems can indeed be challenging, there are solutions that can help you look and feel your best. In this post, we’ll cover 13 of the most common fashion struggles for women over 50 and provide tips on how to overcome them!

common fashion struggles for women over 50 and how to overcome them

green tank | button-down | pants

1. Feeling Invisible in the Fashion World Where Youth Is Prioritized

As you age, it can be easy to feel like the fashion industry has forgotten about you. Many stores prioritize catering to younger age groups, leaving you with limited options for finding stylish clothing that suits your tastes and preferences. You may feel invisible in a sea of bright, youthful clothing and fashion trends like crop tops and ripped jeans that don’t reflect your personal style.

Fortunately, there are ways to overcome this feeling of invisibility and find clothing that fits your style and budget! One solution is to seek out stores that cater specifically to older women, where you’ll find more age-appropriate clothing options. Some ideas are Eileen Fisher, Talbots, and Frank & Eileen.

Another option is to shop the wardrobe basics at “younger” places like Madewell, Everlane, J.Crew, and Banana Republic. Though these stores are geared to a younger audience, wardrobe basics are for any age!

2. Shopping on a Limited Budget As You Approach (or Are in) Retirement Years

As you approach retirement, it’s natural to start thinking about ways to reduce expenses, including shopping for clothes. Shopping on a limited budget can be a struggle for anyone, but for women over 50, it can be especially challenging when you have limited funds but still want to maintain a fashionable and up-to-date wardrobe.

First, it’s important to prioritize quality over quantity. Investing in well-made, timeless pieces that can be worn for years is a better use of your money than constantly buying trendy pieces that may go out of style in a season or two.

Second, look for sales and clearance racks. Shopping during sales and taking advantage of clearance racks can save you a significant amount of money. Also, consider shopping at thrift stores and consignment shops, where you can often find high-quality clothing at a fraction of the cost.

Finally, don’t forget to shop online! Online shopping allows you to compare prices and find the best deals without leaving your home. Many online retailers offer free shipping and easy returns, making it even easier to find great deals on clothing.

3. Deciding What To Keep From Your Younger Wardrobe and What To Toss

As you get older, your style and preferences change. It’s only natural! While you may have loved those low-rise jeans or mini skirts in your 20s, they may no longer feel age-appropriate or flattering now. But, letting go of clothes you’ve had for years can be difficult.

Start by going through your closet and assessing each item. Ask yourself if it still fits well, is in good condition, and if it’s a style you still enjoy wearing. If the answer is yes to all three, then it’s a keeper.

For those items that no longer fit, are damaged, or are out of style, it’s time to say goodbye. Donate them to a charity or give them to a friend who might enjoy them.

You can keep a few sentimental items that you don’t plan on wearing again, but don’t keep items out of guilt. Remember, letting go of old clothes can be freeing and allows room for new, age-appropriate pieces that fit your current style and preferences!

4. Balancing Current Fashion Trends With Age-Appropriate Styles

As a woman over 50, you want a wardrobe that feels timeless yet current, but you also want to dress in a way that is age-appropriate. Balancing these can sometimes be a challenge!

While you don’t have to give up on all trends, it’s important to choose ones that flatter your changing body and suit your personal style. One key tip is to focus on incorporating trends in small doses.

For example, if animal prints are in fashion, try adding a leopard print scarf or a pair of snakeskin boots to your outfit, rather than going head-to-toe in animal print.

Another strategy is to adapt trends to fit your personal style. For instance, if jewel tones are trending and flatter your skin tone, opt for an emerald green necklace to add a pop of color to your ensemble.

5. Dealing With Age-Related Changes Such As Hot Flashes and Other Menopausal Symptoms While Trying To Dress Stylishly

I haven’t experienced it, but I can only assume that menopause is the pits. As a woman over 50, you may often face the challenge of dealing with age-related changes, such as hot flashes. And the last thing you want is to be sweating and uncomfortable in your clothes. So how to navigate this tricky situation?

First, choose clothing made from breathable fabrics, such as cotton or linen. These fabrics allow for better air circulation, helping to keep you cool and comfortable. Look for clothing with moisture-wicking properties, which can help absorb sweat and prevent it from lingering on your skin.

Another tip is to dress in layers. This allows you to easily adjust your clothing based on your body temperature. When experiencing a hot flash, you can remove a layer to cool down, and then add it back when you start feeling cold again.

Also, opt for looser-fitting clothing styles. This allows for better airflow and can help prevent clothing from clinging to your body when you’re feeling sweaty. Look for flowy tops, dresses with an A-line silhouette, or wide-leg pants that provide comfort and allow for better ventilation.

fashion over 50 summer outfit


6. Finding Appropriate Clothing for Work or Special Events That Don’t Make You Look Too Matronly

Whether you continue to work, have your children’s weddings to attend, or both, you may have already found that stylish special occasion dresses for older women are few and far between.

It can be frustrating to feel like you have to choose between looking frumpy and looking too youthful! For work, consider classic pieces like tailored trousers, pencil skirts, or pleated pull-on pants paired with a blouse or blazer. Opt for timeless prints like stripes or houndstooth. You can add personality to your outfit through a statement piece like a chunky necklace or bold scarf. If you prefer dresses, look for shift styles in muted colors or prints.

For events or weddings, you can have a little more fun with your outfit! Try a jumpsuit or a maxi dress. Skip the stuffy matching bolero, and opt for a wrap, cardigan, or stylish blazer instead to elevate a simple dress.

7. Finding Clothing That Flatters Your Changing Body Shape

As you age, your body goes through many changes, and this can make finding clothing that fits and flatters a challenge. But I don’t have to tell you that! Many women over 50 find that their weight redistributes, with more weight settling around the middle, and it’s not as easy to lose weight as it was before.

This can make finding pants, skirts, and dresses that fit well around the waist a real struggle. To overcome this, look for clothing that has a little bit of stretch to it, such as spandex or elastane. This will allow the fabric to hug your curves without feeling too tight or uncomfortable. You might also consider clothing that has built-in shaping or control features, such as tummy control panels in pants or shapewear for dresses. Spanx is a great brand for this.

Another tip is to pay attention to the neckline of tops and dresses. V-neck or scoop necklines can draw the eye upwards towards your face and away from your midsection. Additionally, high-waisted pants and skirts can elongate your legs and give the illusion of a longer torso, helping to balance out any midsection weight gain.

8. Struggling To Find Clothing That Is Age-Appropriate but Still Fashionable

Nobody wants to look like they’re trying too hard to be young. Aging gracefully is a wonderful thing! First, it’s important to recognize that age should not limit your style choices. You can still incorporate trends into your wardrobe, but opt for pieces that are tailored to your body shape and personal style. Embrace classic pieces such as blazers, basic t-shirts, and slim jeans that never go out of style.

Another way to stay stylish is by adding accessories such as scarves, statement jewelry, and beautiful handbags to your outfits. These small details can make a big impact on your overall look.

One of the best ways to balance age appropriate yet stylish is to shop at the brands previously mentioned that cater to your age and style, such as Eileen Fisher, Talbots, and Frank & Eileen. These brands offer classic yet current pieces that are age-appropriate and stylish.

Related: Fashion Over 50: Aging With Grace & Embracing the Size You Are Now

9. Balancing Comfort and Style, Especially for Shoes

I’ve had many women write to me telling me that they want to wear cute shoes, but the cute shoes aren’t agreeing with their feet! As you age, your feet change too, becoming more sensitive and prone to discomfort.

However, that doesn’t mean you have to give up on stylish footwear altogether. The ideal shoes balance comfort and style and have adequate support and cushioning while still looking fashionable.

Here are some tips to find these shoes:

  • Choose shoes with a lower heel: High heels can put extra pressure on your feet and make you more susceptible to slips and falls. Opt for a lower, thicker heel or a comfortable pair of flats instead.
  • Look for cushioned soles: A padded insole or a shoe with a cushioned sole can make a big difference in how comfortable your feet feel throughout the day.
  • Consider orthotic inserts: If you have specific foot issues, custom orthotic inserts can be a game-changer for comfort. Look for shoes that can accommodate these inserts.
  • Invest in quality materials: Shoes made with high-quality materials like leather will mold to your feet over time and offer more support and comfort. Margaux, a high-end shoe brand, is known for having some of the most comfortable shoes.

You may not be able to wear every cute shoe you see, but they exist. If you kiss enough frogs, you’ll find your prince!

common fashion struggles for women over 50 and how to overcome them

10. Feeling Pressured To Dress More Conservatively As You Age

Though there’s nothing wrong with dressing conservatively, society often expects older women to dress in more matronly clothing and are often surprised to see a stylish older woman. No wonder sometimes you feel like you’re losing your style.

But this doesn’t have to be the case! It’s important to remember that style has no age limit and that you can still rock stylish outfits and feel confident in your clothing choices.

The best way to overcome this struggle is to incorporate classic pieces into your wardrobe. Timeless staples like a well-tailored blazer, a stylish trench coat, and a classic pair of jeans can be styled in many different ways and will always be in style. These classic pieces can be paired with more trendy items to create a stylish, age-appropriate look.

Another way to break out of the conservative dressing mold is to experiment with accessories. Adding a statement necklace or a pop of color with a scarf or purse can add some flair to even the most conservative outfits. Plus, accessories are a great way to show off your personality and add some fun to your outfit.

Need help on building a wardrobe from scratch and adding the right wardrobe pieces to your closet? I created a resource for you that will help you build your dream wardrobe!

11. Choosing the Right Undergarments for Different Outfits

Wearing the right undergarments can make a huge difference in the way an outfit looks and feels! But with so many different types of undergarments out there, it can be overwhelming to figure out what to wear with different outfits.

Don’t be afraid to invest in this area. After all, you want to choose undergarments that are comfortable, supportive, and that work well with the specific outfit you’re wearing. This is a tall order!

For example, if you’re wearing a form-fitting dress, you may want to choose a shaping undergarment to smooth out any bumps or lumps. If you’re wearing a sheer blouse, you may want to wear a camisole or nude t-shirt bra underneath.

Related: Top 10 Best Undergarment Brands for Everyday Wear

12. Figuring Out What Looks Best With Gray Hair

One of the biggest visual changes that come with age is the transformation of your hair color, especially as it turns gray. For many women, gray hair can be a challenging change to their beauty routine, but it doesn’t have to be!

Choose a shampoo and conditioner that’s formulated for gray hair to maintain its luster. Also, make sure to keep your hair moisturized to avoid dryness and frizz. Lastly, consider investing in a hair treatment to give it extra shine. Own your color – don’t hide it!

While you embrace your gray, find a cut that works with your hair’s natural texture and density. Whether it’s a sleek bob, textured layers, or even a curly style, there are endless options for every woman. Embracing your gray hair can be liberating and beautiful if done correctly, not to mention it can enhance your style.

Related: 15 Smart Ways To Invest in Your Wardrobe and Make It Better

13. Dealing With Skin Changes

As you age and change, your skin undergoes some changes of its own too. One of the most common skin changes women over 50 experience is a decrease in elasticity and the appearance of fine lines, age spots, and wrinkles. This can make certain clothing styles and fabrics less flattering, and certain colors may emphasize these “imperfections”.

To deal with these skin changes, there are a few things you can do. First, consider visiting a color professional so you can get a list of the best colors to wear for your skin tone. This can do wonders for your appearance and confidence!

Another tip is to pay attention to the neckline of your tops and dresses. As the skin on your neck and chest tends to be more delicate and prone to wrinkling, opting for higher necklines or adding scarves or statement necklaces can draw attention away from these areas.

When it comes to skincare, taking good care of your skin can help minimize the appearance of fine lines, wrinkles, and age spots. Consistently moisturize and protect your skin from the sun’s harmful rays with SPF. Additionally, incorporating products with anti-aging ingredients, such as retinol or hyaluronic acid, can help improve skin texture and tone.

As for makeup, using products that focus on hydration and luminosity can make a big difference in enhancing aging skin. Ditching heavy foundations in favor of tinted moisturizers or BB creams can help achieve a more natural look, while also hydrating the skin. Using a brightening concealer to cover dark circles and spots can also help with achieving a more youthful appearance.

As you get older you may find that you need to tweak your beauty and skincare routine, but just remember, at the end of the day, your skin tells the story of your life, so wear it proudly!

Related: 8 Best Foundations for Aging Skin Over 50

By understanding the common fashion struggles that women over 50 face and how to overcome them, you can now create a wardrobe that is both stylish and comfortable!

For more tips to elevate your over 50 fashion, keep reading: Fight the Frump: 12 Easy Ways You Can Fix Your Frumpy Outfits


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 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.