(Last Updated On: March 17, 2023)

Over 50? Six Tips to Look More Stylish and Less Frumpy

There’s nothing wrong with a desire to be more stylish, fresh, and updated with our clothing style and overall look. As we get older, sometimes it’s easy to get into the habit of wearing the same clothes, or a repetitive style, over and over again because it’s comfortable for us.

Couple that desire for being comfortable, both in the clothes we choose to wear, and the security that particular style of clothing can bring, and we can risk falling over the edge into the world of frumpiness. So if you’re wondering how not to look frumpy, read on, my friend.

how not to look frumpy after 50 - 5 best style tips

The word ‘frumpy’ was first used in the 1840’s, and can also be described as plain, unshapely, and unappealing. I know. Those terms are a bit off-putting, but if we’re being honest, maybe there is a bit of truth in them when we look in the mirror.

Or, we might not see the literal frump in our wardrobe, but decide that it could use a bit of a boost in the style department. You know…we don’t want to look like an old lady!

All that said, if you’re reading this post and thinking, “well, that’s certainly not me…I am quite happy with how I look, my style of clothing, and there is nothing about me that anyone would say was frumpy!”, I say that’s awesome, girlfriend. You might want to just skip right on to another fashion topic that is more relatable. Because frankly, we don’t all struggle with the same things in our lives, do we?

So take this bit of advice and encouragement if it is applicable to you at this time in your life. Keep an open mind and a willingness to try something new, and that frumpy look you’re concerned about will be a thing of the past!

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Frumpy: dressed in an unattractive way; having an old, dull, unflattering, or untidy appearance


6 Best Tips: How Not to Look Frumpy

Most women in their 50s and 60s have a desire to look and feel attractive, which can be a challenge as the days, months, and years go by. We look in the mirror and see ourselves drooping, sagging, and shape-shifting. And, although it is a natural part of aging, it can become discouraging if we let that feeling of “what difference does it make anymore?” overtake us.

So, no…we’re not going to let that happen. One of the ways we can fight that “who cares” attitude is with some simple ways to keep ourselves looking fresh and updated. We’re not supermodels, our figures are not perfect, our skin is not taut and firm. But, so what? We can still feel confident with our choices in clothing, style, and outfits.

If you are determined to understand and live out ‘how not to look frumpy’, read on!

1 | Understand your Personal Style


There is nothing that will give you a style and confidence boost like a true understanding of your own unique personal style. And, it doesn’t matter how simple, unadorned, neutral, or classic you dress.

You have a personal style.

Once you understand and embrace it, girlfriend, you’ll see your wardrobe with new, fresh eyes.

Along with a solid understanding of your personal style is an understanding and acceptance of your body shape. We are all unique in our looks, but there is a pattern to our body shape. When you know how to dress and select clothing that will flatter your figure, it will go a long way toward eliminating the frumpiness.

So, here are some very helpful posts that will show you step-by-step how to define and understand your style and body shape, as well as a few other essential components:

Let’s take that understanding of your personal style to the next step with the rest of these tips to look more stylish in our 50s, 60s, and beyond.

2 | Make sure your clothes fit properly

make sure your clothes fit properly to avoid dressing frumpy

Some women think that by wearing clothes that are a size too big, or a boxy, undefined style, they’ll look slimmer and better. You know…hide all the things you don’t want to everyone to see. The problem with that is, you tend to end up looking frumpy, and if the goal is how not to look frumpy, this approach to dressing just doesn’t cut it.

So, ditch the baggy, slaggy, boxy, hide-it-all look.

If you want to wear a looser fitting top to hide the belly fat, that’s cool. I do that quite regularly these days. But, pair that with pants that are fitted. They don’t have to be leg-huggers if that’s not your jam, but keep them more fitted than loose, and the overall look will be more stylish and updated.

Wear your pants at ankle length, and not dragging over your shoes.

Take stock of your wardrobe – what’s in the closet and residing in the dresser – with a critical eye for anything that is worn out, pulled out of shape, dreary from many trips through the washing machine, etc. It’s better to have a smaller wardrobe (think capsule wardrobe) comprised of the pieces that fit well and make you feel good wearing them, than to hang on to the clothing that should go into the repurpose bin.

find your perfect size with Measure & Made

Hey there friend, do you struggle to find pants, jeans, crops, & capris that fit you well? Yep, most of us have that problem.

Well, take a minute to learn more about Measure & Made, and their unique sizing system called ShapeLogic. Once you find your perfect size, you can buy and wear any of the bottoms on their site and they’ll fit you well!


3 | Trade in the Capris

how not to look frumpy - trade in the capris

You know…those little numbers that end just past the beautiful knee cap. Back in the day we called them pedal-pushers. If you are familiar with that term you’re old, like me. 🙂

Once you pass the age of 50 they’re not cute anymore. Unfortunately, that just-below-the-knee length capri is cutting off at the widest part of your legs, so you are accentuating that area of your body. Now, if you have great, shapely legs, and feel like a million bucks in those knee-length capris, that’s awesome. I’m a little envious of you, to be honest.

And, please don’t hate me for saying this, but the short sleeved, collared button-down shirt isn’t doing you any favors in the fashion department, either. If you love that look and don’t care about style or fashion, and just want to wear them every day, then go for it.

But if you truly want to elevate your style, put them away, girlfriend. You’ll freshen up and un-frumpitize your look. Yes, I just made up that word.

Instead, choose an ankle length fitted pant, jeans, or a longer, fitted capri style pant that ends a couple of inches above your ankles, paired with a longer length top that has a sleeve length you’re comfortable with. (Check out my review of Covered Perfectly for some flattering tunic length tops for women of all sizes and shapes). If the figure is up for it, a tucked in top is a clean, crisp look as well.

4 | Discover some new shopping sources

be open to shopping at new stores for a fresh approach to fashion

If you want to change how you dress, look for a different department, a new online shopping resource, or a store that you’ve passed by and never checked out. Yes, you can still shop at your favorite stores, but instead of making a beeline for the same department, section, or racks, take a fashion risk and walk through the other fashion departments.

You might be surprised at what is in them!

Here are some ideas for you to check out if you’re up for some online shopping:

  • Amazon – yes, shop on Amazon for women’s clothing and accessories. They have come a long, long way in the last few years in this area. You can filter in your preferences in size, style, color, brand, and more. And, think about giving Prime Wardrobe a try. It’s their ‘try before you buy’ program. I have used it before and love the flexibility it offers. I’ll tell you more about Prime Wardrobe here.
  • Nordstrom – you’ll have the option of online shopping with Nordstrom, or possibly retail as well, depending on your area. I’ve found that Nordstrom has quality clothing with a variety of price points. Use their filters for price, color, style, and more, and you might find some interesting, stylish options. It’s worth a look!
  • Chicos – with an eye for mature style, you’ll always find a classic look here. Casual or dressy, it’s worth a look. Check out these slit-hem ankle pants offered in a variety of colors. They’d be perfect with a longer length tunic top.
  • White House Black Market – this is a sister store to Chicos, and is geared toward a more updated look with a younger demographic. That said, however, there are some wonderful options to consider, and you can shop online or retail if available in your area. This could be a great place to shop for layering pieces.
  • Everlane – a manufacturer of ethically made, sustainable fashion, if that is important to you, take a look at what Everlane has to offer. When you’re shopping a slow fashion source you might not find as much variety in the styles, but you’re shopping with a purpose. Another option for layering pieces.
  • Target – similar to Amazon, Target has stepped up their fashion choices, and many of us have a Target store in our area, so we can choose to shop online, pick up in the store, or shop in-store. Most of us will peruse the Women’s department rather than the Juniors, and will find some classic as well as trendy option. The prices are affordable for most, so if fast fashion is workable for you (wear it for a season or two and then repurpose or donate), check out what Target has to offer.

5 | Look at your feet

don't forget the shoes when learning how not to look frumpy

One area of our style that can give us away is what we choose to put on our feet. Of course, if you have health issues that require a certain type of support, the options are more limited.

But for the rest of us, we can choose to take a little bit of a fashion risk with our footwear. There are so many interesting options in shoes that will look better than the sturdy orthopedics, and we don’t have to wear a higher heel.

Flats, mules, low-heeled shoes, sandals…there are a wide variety of material and color options that will look good on us and update our outfits.

6 | It’s not just about the clothes

dressing stylish is more than just the clothes you wear

When we’re talking about how not to look frumpy, it really is about more than the outfit you wear, my friend. It is a total look that includes your hair, skin, accessories, tootsies, and above all, your confidence as a woman over 50.

Here are a few additional thoughts and tips:

  • Create one focal point with your outfit. It might be some really cool shoes, or earrings, or a belt that is in a contrasting color.
  • An all-black outfit can look amazing when it fits properly, the pant or skirt length is flattering, there is an accessory that pops, and you are standing tall, with confidence. Dressing in neutrals can be very cool. Did you know that good posture can make you look slimmer?
  • Pay attention to your skin at this time in your life. Our skin changes as we age and can become dry and drab if we don’t treat it well, with products formulated just for us.
  • Keep an open mind and be willing to try something new. Sure, there are some types of clothes and styles that just aren’t good for us to wear anymore, but don’t cut the options too slim, my friend. If a particular piece is speaking to you, take the time to try it on. It might just be the perfect look for you!
  • remember the hair, the glasses/sunglasses, the jewelry, etc. Similar to our choice in clothes, we can become quite comfortable with that ‘safe’ hairstyle we’ve worn for a long time. I know, because I did that myself. The hair color, too. But I took a leap and went to my natural gray hair as well as experimented with some different styles. And I won’t ever go back! So, consider a new hair style, update the glasses, switch out the jewelry, and see how these changes can take you from frumpy to fabulous.

In Closing: How Not to Look Frumpy

It’s always a bit of a touchy subject when discussing how we look as women over 50. Some of us are fiercely independent, confident, and don’t want anyone even suggesting how they should put an outfit together much less intimate that they might have a little bit of an uninteresting, old lady look about them!

So I certainly hope I haven’t stepped on any toes, but I know because I hear from many women in midlife about the frustration over a changing body shape, weight gain, and decreasing self confidence. We might ‘dress to disappear’ without even realizing it.

Sometimes we can fight back with a fresh approach to how we choose our clothes and accessories. And that’s what these tips are all about. If you’ve been feeling old, uninteresting, not particularly fetching at this stage of life, try opening your mind, your heart, and perhaps your wallet, and see how a fresh approach to style can give you a fresh new outlook!

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how not to look frumpy

2 thoughts on “How Not to Look Frumpy After 50”

  1. I have a probably not a unique problem. But It’s my problem. I own many, many t-shirts. Mainly because I don’t go anywhere but to Walmart or the gym. I look “frumpy” all the time. When I do go somewhere else, I don’t know how to dress. Going out is usually dinner somewhere and then home. I live in Kansas and it is a 1000 degrees here. So blazers and long pants are out most of the time. Also I am about 30 pounds over weight and have no waist. skinny legs. I am kinda shaped like a Mr. Potato guy with tooth pick legs. LOL Hope you can suggest something. Linda

    1. Hi Linda, I can give you a couple of tips. First, check out my post on learning how to dress for your body shape (yours is an apple) for some general tips. For those times when you want to dress a bit more stylish, I’d recommend a tunic style top, doesn’t have to be fancy or expensive, along with a pair of skinny jeans, pants, or leggings. Check out the styles of tunic tops that are made for our midlife bodies from Covered Perfectly. There are many different styles to choose from. I hope this helps!

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