How Not to Look Frumpy: Simple Examples Millennials Midlifers (2023)

5 Fundamentals Of Dressing For Your...

Updated 4-19-2022

How not to look frumpy is a goal for women of any age. Yet it’s such an elusive factor and hard to say it’s ONE thing. I’ve talked about this idea on the blog before, but this time I wanted to get others’ opinions along with showing some simple examples.

Quote of the day: “The best feeling in the world, is to be able to help someone else other than yourself.” Charmaine J. Forde

I always think I know the answer to how not to look frumpy. Yet, then I wondered, what if I was dressing frumpy too, LOL? The idea of asking youngsters for their opinions stemmed from one of my blogger friends, Suzy’s, post “What Your 20-Something Wants to Tell You (and Needs to Hear From You)”.
So here was the question I asked my friend’s kids AND the women in my Forever Fierce FB group (midlife women).

What Do You Consider Old Age Dressing?

I’ll be including some of the answers below along with some simple examples I found on Pinterest of how to not look frumpy. I even included myself as one of the examples.

Definition of Frumpy

Of course how not to look frumpy, one must realize what it means to be frumpy. I shared the definition from the Urban Dictionary in a post here. Yet it still is hard to put your finger on the “ONE THING.” Maybe that’s because there isn’t one thing that makes someone frumpy.

In fact, I always think I can take ANY item and make it look great with modern shoes or accessories or trendy pieces.
Yet when I was researching the idea of how not to look frumpy, I did come up with the perfect opposite of frumpy.
What are they? Chic, vibrant and sexy. Now, remember, sexy does not have to mean showing skin. All three of these opposite connotations evoke the idea of making a statement. Not being invisible.

Millennials Viewpoints

Again the question is What Do You Consider Old Age Dressing?
While I may or may not agree with all of them, I still think it’s interesting to hear the younger generation’s perspective.
1-Non descript, loose and oversized
2-Dress Barn
3-Slacks. Pants that look like jeans but they’re not. They have straight legs with elastic waists.
4-Bermuda shorts, granny panties, and sketchers.
5-Prints that are smaller with bland colors
6-Anything that isn’t revealing
7-Cardigans and vests
8-Floral polyester, short sleeve button-up shirts, most capri pants, camp shirt over a tee.

Midlifer’s Opinions

And here are my generation’s thoughts on the same question.
1-Looking older than you really are.
2-Beige and colorless
3-Ill fitting clothes. Oversized and shapeless
4-Elastic waist pants.
6-Too many rhinestones
7-Nothing current
8-Careless and lacking personality
9-Velcro closing shoes and fanny packs
10-Polyester tops with big flower patterns
Again. I want to point out that with any of these comments above, I think it’s all dependent on how you pair items together. So let’s play a game below.

Make this Outfit Better

This is the game I tend to play when I’m people-watching. Because even though many of the above answers are one kind of item, I still believe you can make almost anything look fashionable.
I wanted to start with something I see ALL THE TIME in my retirement community.

The Red Sweater

Yes, everyone has a red sweater. It’s perfect for Christmas, Valentine’s Day and many other occasions. But let’s break down why this below photo seems like a perfect example of frumpy.
One, it’s shapeless. Two it’s nondescript. And three it’s paired with those grey slacks (read #3 of the millennial’s viewpoint).

Insider tip: The three of us tackled this same idea on the blog this winter. I can sum it up in two words: Focal Point.

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It took me two minutes searching on Pinterest to find examples of how not to look frumpy in a red sweater.

1-Add a modern kind of bottom. You may have thought you’d NEVER wear leather leggings, but I’m here to tell you they are cool. And why not wear them? It only shows what a chic woman you are.
2-Fabulous shoes & the half tuck. If I’ve said it once, I’ve said it a million times. Shoes can make or break an outfit.
The half-tuck can be weird, but it creates a longer leg line. It also can add an interesting detail to the overall look.

How Not to Look Frumpy: Simple Examples Millennials Midlifers (2)
How Not to Look Frumpy: Simple Examples Millennials Midlifers (3)

3-Details & Belt it. The interesting sleeves make the red sweater look chic. Sure, you may complain they get in the way, but I’m sure you can figure out how to push them up when you are eating. A belt can also be an interesting detail.
4-Different shapes. The shark bite shape or any asymmetrical hemline is always more refreshing than one straight across.

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How Not to Look Frumpy: Simple Examples Millennials Midlifers (5)

Here is Charlotte and Lesley showing how it can be done below.

Looking for examples from our site with older women for these suggestions? Here are the examples from my suggestions
1-Charlotte wearing red and leopard #1 suggestion
2-Lesley and the faux half tuck #2 suggestion with the half tuck
3-Fabulous shoes #2 suggestion with the shoes.

Another Make this Outfit Better

This next example of how not to look frumpy is more about a pairing as opposed to one item. I pick on the concept of matching/nonmatching because it’s part of my color recipe that can make our wardrobes bigger and more modern.

While matching is the way we were taught to dress and is easy, it can come across as old ladyish. One thing to remember is style changes. And you may think it’s hard to change what you’ve known and liked for so long. But I’d ask you to think of change in another way.
Have you ever pushed for women to be equals in the workforce or maybe for equal pay? These ideas of change are value based and much more significant than clothing. Yet we’ve pushed for them and expect them.
This is how I know we can ALL change our fashion style too. Change is a good thing and evolution is important.


I saw this photo on Pinterest and thought to myself that this pink skirt is really pretty. However, the fact that the oversized, floral top, matching jewelry, and black “classic” shoes are paired with it, makes the look old ladyish. (I realize it’s worn by an old lady, but even a 20-year-old in this exact outfit would look frumpy).

Therefore I quickly searched Pinterest and found 4 other examples to show how a pink, midi skirt could be worn to look better. Most of these include the idea of dichotomy or yin/yang.
For the frumpy example, I could also point out that the materials are the same. If you are always combining cotton items with cotton, you aren’t taking into account contrary textures.

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1-Statement Jewelry with Dichotomy. Adding bling with statement jewelry especially over a top that is opposite of it always is fun. You may consider a striped turtleneck as casual, but the addition of a statement necklace brings an element of surprise and vibrancy.
2-Denim and Shoes. Denim is a great way to add a casual flair to any skirt or dress. And a fun print shoe gives two solid pieces more personality.

Insider tip: I’ve showcased 5 different ways to wear a chambray shirt. If you don’t have one yet, make sure to add one to your fall style.

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How Not to Look Frumpy: Simple Examples Millennials Midlifers (10)

3-Graphic Tee and Sneakers. Both the graphic tee and the sneakers are part of the yin/yang which can make any skirt outfit more modern. Notice the half-tuck again. The half tuck can help the proportion. In fact, I would argue that the longer skirt below is more pleasing to the eye because of its proportion.
4-Denim Jacket & Purse. Here’s a staple that can cover almost any frumpy top. If your top seems ill-fitting then a modern jacket is a trick to pull it all together. In fact, I would argue, you could add a denim jacket to the original frumpy look and it would be 10X better.
That and an add-on trendy purse will be a great focal point.

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How Not to Look Frumpy: Simple Examples Millennials Midlifers (12)

Here are both Charlotte and Lesley working on adding more than just 2 colors to an outfit.

As for examples from my site with older women, they can be found below
1-Statement necklaces by layering #1 suggestion
2-Cathie wearing sneakers and skirt Cathie shows how the #3 suggestion works so well
3-Graphic tee and skirt #3 suggestion

How Not to Look Frumpy the JTouchofStyle Way

I almost purged these beige, linen pants. Why? Because I took them out one day and the word “frumpy” came to mind. In fact, I went as far as putting them in the giveaway pile before I realized that I should prove that I could make them stylish.

What’s wrong with the outfit below? I could seriously wear any one of these items with other pieces and look nonfrumpy. This is why they aren’t great together.
1-Too many wrinkles. While I’m all about embracing wrinkles to a degree, too much can look too sloppy. This is one reason it’s good to combine different materials in an outfit.
2-Nothing fitted. Not that your items need to be tight, but there is no shaping in this look.
3-No focal point. Everything blends together instead of having something fun to look at.
4-Bland Colors. See #3 above.

Related post: How to coordinate your looks with dichotomy, color, and proportion

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Beige and linen. They could be a recipe for frump very easily. Yet I took the dichotomy idea along with some great shoes to make them into an outfit that I felt fabulous wearing.
1-This top. The silkier top with the fun sleeves and tied knot front has all kinds of interest. It’s also nice because the hemline creates that half-tuck.
2-SHOES! You don’t have to wear heels, but you need at least a couple of pairs of shoes with personality. Maybe that’s a print, animal print or a bright color.
3-Statement earrings. Your earrings should be there to bring people’s attention to your face. Remember that when you always reach for a small pair.

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Interesting Color Combinations

This could be an entire post in itself. But I would be remiss not to mention that color combinations can be impactful. It’s the opposite of many of the comments regarding how frumpy is bland and colorless.

Insider tip: If you need help with different ways to combine colors, make sure to check out my color recipe post.

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In Conclusion

Here are a couple of ideas on how not to look frumpy.
1-Make sure your tops have some kind of interesting detail. Don’t think that a print is always the answer. Think interesting hemline, neckline, or sleeve.
2-If you have a boring top, add in a fabulous scarf, necklace, or jacket
3-Shoes. Always update and make sure your shoes don’t look orthopedic.
4-Color. First, make sure you wear colors next to your face that look good on you. Second, have fun combining colors you haven’t worn together before.
5-Start shopping at other stores. If you wear what you’ve always worn, you will never look any different.
6-Stop saying I can’t wear that. You are limiting yourself and not having fun. TRY EVERYTHING.

Insider tip: There are ways to find your best colors. I compared a couple of online options here.

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Photo credit:Rob Filogomo & Pinterest

My Goal

Thank you for visiting my space on the internet. I like to showcase how it’s never too late to look great for women of any age, size, or working with any budget.
I feel I’m here to help move beyond the fashion rules of yesterday and evolve. Style and clothes are made to give you joy. Not cause us stress because we are worried about what others think.

My hope is that you get ideas and inspiration from Charlotte, Lesley, and myself. It’s not about copying what we wear, but about using what you already have and updating items along the way.
Most of all it’s getting us to think differently and dare I say, have fun.


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