31 Street Style Outfits For Women Over 40 & 50

Street style outfits for women over 40 & 50: Fashion is perhaps the most empowering tool for a woman. Especially at the ages of 30, and 40. Since women at this age feel comfortable with themselves, they know what they want, and what they feel comfortable in. Similarly, they are unapologetic.

Take advantage of all of these freeing features of being 40 and take the time to invest them into your clothes. After all, clothing is a form of self-expression like any other. And only when you are truly mature, you are able to use your clothes to speak to those around you.

Moreover, be ready to see outfits that are going to refresh your wardrobe. We have prepared a rundown of outfits perfect for any occasion, and style.

How Should Women Over 40 Dress Street Style?

Many people hear the words street style and interpret it as white t-shirts, and oversized ripped jeans. However, street style has lost this image a long time ago and is now even considered the most fashionable and expressive part of fashion.

Moreover, it is not about one style or one occasion. After all street style became infamous because of models and celebrities being photographed on the streets by the paparazzi. And as most of us, these individuals were on their way to a plethora of events and occasions, this is what makes street style so relatable and transferrable.

No matter what occasion or time of day, there is a street-style outfit perfect for you. Although that is not to say that street style doesn’t have a unanimous appeal, here are some things to note:

  • Shoes: comfortable shoes prevail in street-style outfits. Primarily because people walking through the cobbled streets of fashion capitals would prefer to remain on the side of functionality. You should do the same.
  • Layering: as could be predicted leaving the house without a drive requires you to be prepared for weather changes. Therefore people layer clothes. This is perfect for a windy day, or a spring day when the weather can change without precedent and catch you off guard. For which peeling some layers off remains a necessity. Here are some tips on how to Layer Your Clothes Like a Pro.
  • No Gowns: Although this style is applicable for all occasions, one rule prevails. People in gowns don’t walk the streets, they are driven off to their glamorous events. So if you want to portray a street style aesthetic, you will avoid fancy long gowns.
30 Street Style Outfits For Women Over 40 & 50

31 – Stay Breezy in Maxi Dresses

For Summers, Maxi dresses, as well as tiered dresses, are a must-have as they can easily be dressed up or down without compromising on comfort. Here are some expert Dressing Tips for 40 Plus Women.

30 Street Style Outfits For Women Over 40 & 50

30 – Keep it Casual with a White Blouse and Jeans

Even if you aim to look stylish and chic there is no need to reach directly for a dress. A pair of casual jeans and a shirt will do. The secret lies simply in the way you style it. Try going for a light wash on the boyfriend jeans. Pair it together with a light blouse, but keep it unbuttoned, with a shirt underneath. Next, try to keep it light on the top colors. So match the shirt with a light brown blazer.

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29 – Casual Yet Chic with a Chanel Lookalike Blazer

If you have a pair of blue jeans laying around but you want to mmaake them look more special, try this look. All you will need is a white shirt that you most likely already have in your closet. Similarly, try looking around for a Chanel lookalike blazer. These are usually made in a spectrum of colors, and resemble the classic Chanel look. So have your pick. Top off the outfit with some layered jewelry and you’ll look amazing.

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28 – Pair Loose Cotton Based Top and Bottoms

Third, on the list of casual but equally as chic street style looks, is a very simple one. Since it only requires two pieces of clothing. Moreover, these are incredibly versatile, and you might even have them in your closet already. This outfit requires some loose light blue pants and a loose navy blouse top to match.

30 Street Style Outfits For Women Over 40 & 50

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27 – Match Your Brown Shoes to Your Purse

Most of the time casual street style looks are made special by the intricate layering and matching of accessories. For instance, your scarf and your bag, or your shoes and your bag. In this particular outfit, the focal point is the light brown shoes matching the same colored bag. Bonus points if the color and textile match.

30 Street Style Outfits For Women Over 40 & 50

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26 – Match Your Belt to Your Bag

Similar to the look above, we suggest you try pairing your belt perfectly with your bag. This correlation screams sophisticated outfits for women over 40. Moreover, when paired with an all-grey base look, you will really stand out.

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25 – Go Bold with an Unusual Green Top

Even the simplest type of outfit can be made into an uplifted street-style alternative. The key to this trick is the color of your top. So if you have the desire to wear some jeans and a blouse. Try first to spice it up with an unusual choice of a blouse. To create an even bigger contrast we suggest that you pair it with some white jeans. Since they will be so neutral they will really make the bright blouse pop.

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24 – Go For a Classic Black and White Look

There is nothing bad about an old-school classic. Even when choosing the basic black and white colors for a street-style outfit, you can make it your own. For instance, there is always room to play with the size and fit of your blazer and pants. In this particular look, the approach is elegant. Therefore you see slim-fitting pants. The same could be said for the blazer. Although an alternative would be with wide pants and a box-shaped blazer.

30 Street Style Outfits For Women Over 40 & 50

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23 – Spark the Look Up with a Bright Red Heel

Similar to the previous look, this is a classic black and white combo. Instead of a black pair of pants though, try to go for white jeans. However, the key to this look is the surprising pop of bright red on the shoes. Street style is often all about making a necessary infusion of color, however, remember to apply it sparingly for the perfect effect.

To learn more about red heels read here!

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22 – Layer a Variety of Denim Clothes

Streetstyle is often time about layering similar clothes, but ones that differ slightly. This achieves the desired layering and juxtaposition. This is easily accomplished with denim, as it comes in so many colors and finishes. This outfit shows just how to do this well. Try pairing a jean shirt, and jeans with slightly different color finishes. Pair with a grey blazer on top.

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21 – Don’t Be Afraid of Ripped Jeans

Speaking of denim, jeans come in a plethora of styles nowadays, and it’s necessary to keep up. So put the worries that ripped jeans are not aged appropriate. Inversely they are the perfect amount of confidence and youth. Therefore make for the perfect street style jeans for women over 40. To maintain composure in the look, pair it with a classic black turtleneck.

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20 – Downplay Rugged Ripped Jeans with Pastel Colors

Opposite to the previous outfit, it is also possible to challenge the rugged look of ripped denim. For instance, pair with pastel colors at the top of your outfit. This will achieve a unique approach, that street style is often renowned for. You should also check out these Jumpsuit Outfits for Women Over 50.

30 Street Style Outfits For Women Over 40 & 50

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19 – If You are Getting an Oversized Blazer, Go Classic with Plaid

Oversized clothes, similar to ripped jeans can be an overwhelming choice and may seem out of your comfort zone. However, if you feel these clothes calling your name, don’t stray away. While you are choosing the perfect oversized blazer, find solace in picking one up in a classic print. You can never go wrong with a black and white plaid.

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18 – Match the Flaired Silhouette of Your Shirt to a Bag

The recent evolution of bags into mini purses has caused a surge of new bag shapes. One of the most widespread and fashionable options is the half-circle bag. Especially in a woven finish. Compliment the shape of this purse, by pairing it with an equally flowy and gentle top. Continue the shape even in the jewelry.

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17 – Look Put Together in Light Tones with the Right Accessories

Nothing says put together like beige and pearls. Try pairing a loose-fitted pair of beige pants, with your favorite most comfortable white long sleeve. After all fashion can and should be comfortable, and this is certainly a comfortable outfit for women over 40. One way to maintain the street style aesthetic is the jewelry. Oftentimes, even a simple top can look elevated with the right necklace.

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16 – Match Beige and Black for an Expensive Aesthetic

Similar to the previous look, the color beige has a notorious expensive appeal. Especially if paired with the right complementing pieces of clothing. For instance, pair it with a slightly unbuttoned blouse, and black office pants. But one more, most importantly choose your accessories wisely. These Chanel – like layered necklaces will take your look from casual to fancy.

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15 – Pay Attention to Fabric Finish, to Give You the Desired Look

Yet another variation on the color beige, although this time a far more casual hip aesthetic. The only thing changing the way the outfit presents itself is the fabric finish, as well as the fit of the clothes. The firm cotton and the voluminous loose shapes will give you a hip outfit.

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14 – Dial Down Animal Prints with Beige

Following on with the different ways to style beige clothing, this outfit allows you to use it as a moderator. For instance, we all know that at times animal prints like cheetah, zebra, or snake can be perceived as vulgar and bold. On the days you want to balance a top like that out, just pair it with a pair of beige pants. Beige is a neutral color and thus acts as a neutralizer for even the boldest of prints.

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13 – Mix a Beige Base Outfit with Any Coat You Like

Last but not least on this part of beige outfit pairings, is this wonderful street style look. It shows just how easy it is to make a seemingly difficult coat work. At times, when you have a very bright clothing article to the style try pairing it with beige. Although white and black are also neutral colors, they are quite extreme on each end of the spectrum, and thus actually make the bright colors pop. Whereas beige is both neutral, and a neutralizer.

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12 – Go For All Blue with a Hint of Stripes

Some patterns and colors are notorious for mixing well together. For instance the classic mix of navy and stripes. This pairing gives a hint of a sailor and is very refreshing. Wear this when you want a put-together, casual and comfortable outfit.

30 Street Style Outfits For Women Over 40 & 50

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11 – Pair Blues and Checkered Prints Together

Similar to the outfit above, the choice of blue with a checkered print is similarly fashionable. However, this print is much more put together, therefore will work well in looks that aim to be worn to more dressy occasions. For that very same reason, pair this with a pair of striking blue heels.

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10 – Black and White Outfit that Lets Your Remain Comfortable

This is the last outfit in our casual outfits for women over 40 section. It is special because it is versatile. No matter what your style is, no matter your body type or height – it will fit you and will make you look dashing.

The secret is the blacktop and pants that always make you look stunning. Pair with a large gold necklace if you need to elevate this outfit. Here are some Dating Outfits For Women Over 40.

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9 – Match the Textures of a Pleated Skirt and Leather Jacket

Streetstyle is all about textures, and unique pairings. This first outfit in the more fashionable outfits of this rundown revolves around this rule. Match the texture of a pleated skirt, to a glossy finish of a leather jacket. Bonus points if you manage to find both these items in the same color palette because the correlation of color is important to maintain when textures differ.

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8 – Wear a Mustard Yellow Head to Toe

Although some women might want to stray away from bright colors in their forties, that is not the rule for everyone. So if you have the desire to play around with color, here is how to do it well. Firstly choose a color that is bright but muted. So instead of a bright cannery yellow, choose a mustard yellow. As it looks more mature for a head-to-toe look. Secondly find items that are reserved, like a sweater and a pair of pants. Since it’s important to maintain balance.

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7 – Wear a Forest Green Head to Toe

Similar to the previous outfit, this is also a head-to-toe look. Although we wanted to show you an alternative to a bright color. So this look focuses on a deep green co-ord. To prevent the outfit from looking too dark and gloomy, it is recommended to pair it with a white blouse. Have it stick out from underneath the hem, or sleeves to add pops of color.

30 Street Style Outfits For Women Over 40 & 50

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6 – Mix Three Different Colors Together for a Fun Look

If you are mixing two colors, that is difficult enough, however, three is a bit more complicated. The most important rules are to choose at least one neutral color like black or white. Or both. As well as to match one of the colors to your bag and shoes, to avoid having accessories add another color.

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5 – Pair the Colors of Your Top to Parts of the Pattern on your Pants

Especially if you intend to wear plaid or checkered pants, maintain this rule. This is an easy way to create a showstopping outfit, without worrying too much. Choose a plaid color that goes as adventurous as you would like. Next, match a blazer to one of the stripes on the pants, and here you can choose the most unique and bright one.

30 Street Style Outfits For Women Over 40 & 50

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4 – Try Out a Highwaisted Ankle-Length Pair of Pants

Another way to create a fashionable look apart from playing with color – is silhouette. Try out a new style of pants you most likely haven’t before. Like these high-waisted, but cut at the ankle wide pants. Get them in a statement but muted color.

30 Street Style Outfits For Women Over 40 & 50

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3 – Wear a Striped Skirt and Bright Red Coat

Similar to the tip from a few outfits ago, pairing the color of your top to the pattern on your bottoms is a foul-proof way to integrate color into your outfit. Another example is this stunning pairing of a striped pencil skirt with a red coat.

30 Street Style Outfits For Women Over 40 & 50

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2 – Wear Two Patterns Together

As we are nearing the end of the list, the outfits are getting riskier and riskier. And if you are brave and experimental enough, we are here to give you tips on how to do it right. For instance, when pairing two different patterns together, remember the rule of neutrality.

Have one of the patterns remain beige/brown, whilst the other can be as bright as you want.

30 Street Style Outfits For Women Over 40 & 50

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1 – Mix Together the Reds and Pinks

Last but certainly not least on the list is a wonderful mix of bright colors. Often these are regarded as a faux pas, but not with us. Instead, we believe that if paired in the right forms, this makes for a really unique look. Most importantly contrast the playful colors, with controlled forms. So long straight pants and a classic sweater/turtleneck are the ones to go for.

30 Street Style Outfits For Women Over 40 & 50

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Frequently Asked Questions

Q. How do you dress chic at 40?

Dressing chic is partially dependent on the latest trends, and partially on wearing what feels comfortable. Aside from paying attention to what is on the most recent catwalk, try to figure out what makes you feel most confident. Take into consideration comfort, sizing, and type of materials – choose the softest, silkiest ones. As soon as you feel at home in your clothes, you will look chic.

Q. What should a 40 year old woman wear?

Wear something extra comfortable, and don’t be afraid of youthful pieces of clothing. Try our bright colors, like greens and blues. And mix and match them with some prints. Like a classic cheetah or leopard for example.



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