Originally published May 23, 2024.
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Matchy-matchy outfits, frumpy flats, oversized everything? Here are the style mistakes I avoid over 40, 50 and 60, and what to wear instead.
By Liz · · 10 min read

Originally published May 23, 2024.
This post contains affiliate links. If you buy through them, I may earn a small commission at no extra cost to you. Affiliate disclosure.
While wrinkles are inevitable, style blunders are surely avoidable. Fashion is all about expressing yourself and uplifting yourself, regardless of your age. Growing old doesn't mean you have to ditch your fashion sense and wear clothes that miss the mark and make you look old.
Who said that there isn’t any fashion for women over 40? Many ladies miss out on the joy of dressing up after a certain age or fight aging gracefully. Falling instead for chasing the fountain of youth, chasing the past for far too long, or just giving up and saying I am old who cares or I earned to dress this way.
This information isn't to age shame nor to dance around the truth. So take what you like and leave the rest, but maybe keep these helpful insights in mind.
Today I will share my best tips for beautiful ladies to save themselves from committing fashion over 40 disasters while getting dressed:
Matching shoes, matching bags, and matching accessories are a page out of the old catalogs and magazines. Gone are those days when dressing up in the same exact color head to toe that one store or one brand is pushing is not fashionable. As we get into our 40's, 50's and beyond an overly matching set can look aging or even worse like you are simply wearing pajamas.
Instead, I would recommend trying a monochrome look This a personal favorite of mine, it is so easily, yet so elevating. It certainly ensures a flawless ensemble every time. Not only does it make you look classy, but it also unlocks timeless and an elevated look without trying too hard.
To get started with your monochromatic look, a pro tip is to shop for a piece of clothing from one shop and match its coordinates by shopping from other shops. For example, if you find a pink pair of trousers from a shop you love, do not shop for a pink shirt, blazer, and accessories from the same shop; instead, look at others store or even other brands or maybe even other textures to buy the other pieces to finish your look.
This will give you different textures, different shades of pink, and varying tones, which, when coupled with each other, will make you look more fashionable and polished. And I think the hunt to gather these outfits are fun as well!
The love for chunky jewelry is difficult to fade away. Irrespective of age, women of all ages are prone to fall in love with chunky jewelry pieces. There are so many gorgeous options out there, I know! But, if you want to stay looking modern and fresh, you need to exercise caution and not overdo your accessories all at once.
Refrain from wearing several chunky jewelry pieces at once. Instead opt for wearing one of your favorite statement piece at a time, instead of wearing it in bunches or sets. Another thing I would advise against, is don't wear huge earrings. The classic large vintage looking earrings or the big statement earrings, we loved in our 20's and 30's from the 70's-90's...can now make us look like we are from that yesteryear as well. Instead, keep it current, keep it sassy and opt for hoops. I find hoops in varying sizes to still add a casual vibe to any look and also a bit of youthful essence as well. I have seen them on ladies from 18-90 and they just seem to always work. Oversized earrings can be heavy and pull on the delicate skin, already losing collagen and make your ear structure change faster and even make your face appear more bulky or saggy in the lower half. So just keep it simple. Less is definitely more in this department.
A statement bracelet can also enhance your look and prove to be a useful and sassy addition to your ensemble.
Oh the oversized trend. I can't wait for this one to pass. Can the 6 foot tall models pull it off, yes! But that isn't a fair question they look good in anything. I have more recently seen many middle-aged ladies fashionistas, where they pair an oversized shirt or sweater and pair it with baggy pants trying to hide weight or trying to be on trend. But this is actually completely wrong! While it may be pretty tempting to opt for oversized clothing to conceal your weight, such clothes can hamper your overall appearance and make you look heavier, frumpy, and older than you actually are. And trying to chase trends that just don't suit us, makes for photos we will cringe at in no time at all.
While wearing oversized tees and sweaters can be fine, the catch lies in how you style them! For example, an oversized classic tennis sweater with a V-neck, is attention grabbing and stylish tucked in somewhere with the sleeves rolled up and with some hoop earrings for a touch of sparkle. Further style this outfit with some gorgeous pumps or boots and a pop of color purse....you will certainly be gathering compliments while out running your everyday errands! This type of styling magic can make you look a few years younger instantly.
Either wear well-fitted clothes or style your oversized garments right, so that those clothes do not swallow your figure, giving you a sloppy aging appearance.
Ladies, let me tell you one of the top styling tips you have to know....shoes will make or break your overall outfit. Growing old doesn't mean that you have to look for granny shoes that give you an outdated look. Many who complain of backache, knee pain, and other health issues usually end up settling for old lady frumpy shoes.
But there are so many cute, stylish, and comfy shoes on the market these days, that you can buy without breaking your bank. Seek these out and save yourself money and time in purchasing ugly shoes that instantly hit the fast-forward button to make you look older than you are. Step into something fabulous, add support, there are comfy stylish shoes out there. Yes, there are even stylish orthopedic shoes as well if you have painful issues that require a bit more support.
Sometimes covering up too much isn't a good look either, as it can come off as too matronly and that can be an aging look. As we age, we often times try to cover problem areas and I totally get it, things change fast sometimes whether we like it or not. I myself have chosen high necklines to camouflage those bothersome chest wrinkles that usually result from side sleeping. It is a normal thing that comes with age and seems to, like many other things worsen as time goes on. So to save yourself from accruing those chest wrinkles and still leave open chest barring tops, consider scooping up a wedge pillow to sleep on your back instead of side sleeping.
Once you clear up or even minimize those lines on your chest you can confidently wear a v-neck top or button-down shirt to look for a sassy and stylish modern look. Discover the different range of neckline options available to achieve a look that highlights your personality.
I advise to just skip all trendy denim, unless you like buying things over and over again. But specifically here we will discuss trendy denim pants, more specifically for mature women. These styles can not translate the way you see it in your mind or on that model at the GAP that is 22! Oversized jeans can make you look a size or two bigger than your actual size. Cropped pants can make you look both shorter in height and bigger in size. Distressed denim can make you look like you are trying too hard to be 20 or 30 again. While embellished denim can come off as frumpy, scattered, juvenile or as a billboard for a brand you aren't hired to be showcasing.
Stay away from distressed, embellished, and tapered pants because not everything that is trending looks good when you cross your 40s and 50s. Straight cut, boot cut, and a wide leg pant are the best for us fashionistas over 40**. They are timeless and look stunning no matter your age.** Stay classy my friends.
Too many ruffles may look cute but on two-year-olds and little girls and even young women can pull offf a bit more ruffle. But for us ladies that are a bit older, I have to say, it can look juvenile or like you are trying to hard to look young. Fashionable women of all ages, who look to fashion trends and add a tasteful touch of ruffles here and there to accentuate your overall style really nail this. In general middle-aged women should opt fewer ruffles because skirts, shirts, and blouses with ruffles everywhere may not look stylish on us as we age and make us look bulky and heavier.
The combination of socks and sandals seems to works stylishly for teens and athletes, but when it is on a mature woman, it silently screams the ultimate grandma attire. And this you can sometimes see this clearly and sometimes we can't, so this is an example where maybe you totally agree with this assessment. When socks meet sandals, it presents a granny glam quotient that makes you look way older. This style for women over 40 is a hard, NO. Just avoid it all cost.
Now, if you HAVE to wear compression socks or supportive socks and you cannot avoid them in the daytime, make sure that you do not wear knee-length skirts or short dresses that showcase them and certainly don't wear the sandals these days. Instead, opt for trousers or a long maxi dresses or maxi skirt instead, to cover this fashion faux pas and chose a chic shoe that looks good and is supportive as well.
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These styling mistakes can make you age faster than a time machine malfunction. So, make sure that you do not commit any of these women-over-40-fashion disasters because life is too short to get yourself caught in a fashion funk!
But do remember ladies, fashion is fun and fashion is subjective. If you love to wear anything that I have said not to wear, you go for it; after all, fashion is all about feeling good about yourself. If you love something, go for it without any fear!
Keep watching: What NOT to Wear Over 40, 50, 60+ · Tummy-Minimizing Style Tips · Must-Have Flat Shoes for Stylish Women · No-Tuck Tops for Women Over 40
Shop my picks: My Amazon storefront · My outfits on LTK
Related: 10 Ways to Refresh Your Wardrobe After 40 · How to Dress for Your Body Shape After 40 · 10 Things You're Doing That Age You After 40
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This post contains affiliate links. As an Amazon Associate I earn from qualifying purchases. If you purchase through one of my links, I may earn a commission at no additional cost to you. I only share products I genuinely use, like or think may be helpful.
This post may contain affiliate links. I may earn a small commission at no extra cost to you.
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LizLiz is the creator of Stylish & Grateful — helping women over 40 look better, feel better, and live better.
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This post contains affiliate links. As an Amazon Associate I earn from qualifying purchases. If you purchase through one of my links, I may earn a commission at no additional cost to you. I only share products I genuinely use, like or think may be helpful.

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