outfits for women over 40

Radiate Confidence With These Outfits for Women Over 40

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Like many things, style can be a difficult thing to navigate as we go through changes in our lives. Ranging from things like finding a new personal preference to forming new style goals and everything in between, there are a lot of things to consider when we are trying to formulate the perfect outfit – whether it be styling evening wear, incorporating animal prints into your looks, or donning classic styles while still being able to give off a more relaxed feel. 

As you can probably tell, there are hundreds of different objectives that one can have when it comes to achieving a great look; no matter what yours is, the trick is simple – finding the pieces that bring out your confidence and that truly feel make up your own personal style!

Easier said than done, I know. But definitely possible! I’m here to walk you through some curated outfit ideas, where we talk about pieces that work and why, along with a little style tip here and there along the way. Ready to go? Let’s do it. 

1. maxi dress + block heels + stud earrings + cuff + crossbody bag

outfits for women over 40

dress | shoes | earrings | cuff | bag

When it comes to chic silhouettes in dresses, loose structures and oversized fits can be a great option. Beyond keeping you comfortable and elegant with its a-line design, this Banana Republic dress also features two different fabrics – crepe at the front, and satin at the back. This subtle yet intentional detail takes this dress to the next level, emphasizing its flowy characteristics while requiring minimal effort. 

For accessories, get inspired by the color of your dress! These matching ruby stud earrings and cuff make for the ideal pair, dressing up this sophisticated look. For shoes, a nude block heel and a nude crossbody bag tie it all together, once again offering comfort, practicality, and style at the same time. 

This would be a great outfit to wear as a wedding guest, to a formal night on a cruise (check out the gorgeous green color this dress is offered in), or to any other special occasion or formal event.

2. maxi dress + dangle earrings + ankle boots + leather belt + gold ring

outfits for women over 40

dress | earrings | shoes | belt | ring

Featuring a maxi length, a mock neck detail, and mid-length sleeves, this dress makes for an instantly elevated outfit for tons of different occasions. Asymmetrical pleats at the front give this dress movement and flow without taking away from its chic structure, while its jersey fabric keeps this style comfortable as well. 

While this dress can easily stand on its own when it comes to creating an outfit, simple accessories can also easily transform this piece as well.

Add a brown leather belt to your waist (make sure to get the right size for this area!), adding even more definition to the structure of the design and your figure. 

Subtle yet intentional gold jewelry also takes this outfit one step further. These dangle earrings with smoky quartz are a great option to go along with the mock neck feature of the dress; especially with your hair tied back, this accessory allows you to create visual interest and balance without overwhelming the ensemble!

Add a gold ring to tie it together, and finish it off with these brown ankle boots (that feel like socks) that continue the elegant (yet still practical) essence of this outfit with its material and silhouette. 

3. black dress + twist heel + oversized coat + stone drop earrings 

outfits for women over 40 (3)

dress | heels | coat | earrings

No matter your age, individual style, and personal fashion-related needs, there’s no escaping a little black dress! This all-star closet staple comes in an endless number of forms, always providing easy, versatile, and classy ways to pull an outfit together. 

This crepe LBD makes for an incredibly flattering fit due to its design details. Draped at the front, this piece also features Dolman-style sleeves and a v-neckline that transforms into front detail that cinches in at the waist. 

Working to effortlessly enhance your figure, this dress creates the perfect balance, making it a perfect choice for both your selection of work outfits or for happy hour drinks with friends. 

Dress this look down slightly with an oversized knit coat that provides warmth and balances the elegant feel of the dress. Beyond making this piece perfect for the daytime, this piece also gives this outfit the perfect transitional quality, allowing it to transform with the switch of one element. 

Stand and walk on these shoes all day, worry-free – it turns out there is really no need to sacrifice comfort for looks! The Day Twist heel is designed to keep your feet moving pain-free, while also giving us a simple, beautiful silhouette that’s ideal for an endless amount of looks. 

Finish this simple and versatile look off with a pair of stone drop earrings for a touch of something extra! 

4. wide-leg wool pant + cashmere sweater vest + ankle boot + leather tote

women over 40 outfits

pants | vest | shoes | bag

While I love mixing lighter neutral colors for an easy, elegant color palette, dark neutrals have their own appeal when it comes to creating simple, truly elegant looks. 

These wide-leg Italian wool pants set the tone for this look with their subtle black and brown pattern. Double-pleated at the front, these trousers also feature both a relaxed fit and a super high waist that works to both flatter and provide comfort throughout the day. 

Balance the oversized look of the pants with a sleek cashmere crewneck sweater, bringing in both a lighter shade and a simpler silhouette to complement the look. 

For accessories, a black boot and a black leather tote tie in the black details from the pants, making for a cohesive, elegant, and clean outfit that might just become a weekly go-to! 

Related: 10 Easy Ways to Make Cute Outfits with Simple Clothes

5. polo top + wool pant + leather loafer + classic blazer + stud earrings 

outfits for women over 40 (5)

top | pants | shoes | blazer | studs

For yet another chic look that can be taken from the office to dinner with friends and a pit stop at your favorite wine bar, this outfit might be the answer to your fashion dreams.

Making use of various classic pieces, this look bets on simple silhouettes and an even more simple color scheme for its charm.

Start off with this wool-blend polo top, adding a simple base to the look while still contributing its own style detail. The polo collar detail adds its own flair to the look, still making for an interesting look when the third piece comes off. 

On the bottom, these wide-leg Italian wool trousers give this piece a soft structure, making for a clean look that is still comfortable and non-restrictive throughout your day. These high-waisted pants also feature a flattering fit through their design, including details like a pleated front. 

Layer these pieces with a classic black blazer that adds both more structure and personality to the look. End things off with a timeless pair of loafers and some stud earrings for an extra final touch. 

6. oversized shirt + straight jeans + cashmere crop sweater + leather ankle boot

idea for women over 40

shirt | jeans | sweater | boots

A great, laid-back outfit doesn’t have to mean sweatpants and your favorite old t-shirt – while we certainly love that combination, sometimes dressing casually can be just as chic as dressing up!

This basic everyday look is all about great, wardrobe essentials that fit well. Finding items like these that you truly love and feel great in is well more than half the battle. 

Here, we are starting with an oversized shirt. Besides being incredibly stylish, oversized shirts are also incredibly easy to style and wear, providing comfort throughout the day while giving off a very intentional and elegant feel to your look.

When it comes to styling, I personally love a few simple tweaks like rolling up your sleeves to your elbows and opening up the front. Here, the choice is truly yours on whether you want to tuck in your shirt all the way, halfway, or leave it be – all three options are great and chic ways to style this piece.

On the bottom, these 90s-inspired straight jeans are as classic as it gets. Providing plenty of support and lift, these blue jeans pride themselves on having the right fit that will earn them a spot in your permanent denim rotation. 

Throw this cashmere cable-knit sweater over your shoulders, adding texture to your outfit, as well as both a classic and a slightly more modern element to your look with its cropped design. Especially as we begin to think of easing into spring, a simple sweater tied over your shoulder can add a stylish and effortless layer of warmth to your look. 

For shoes, finish off this ensemble with this leather ankle boot that’ll keep your feet warm and your outfit balanced! 

7. sweater + wide-leg pant + ballet flat + silver earrings

outfits for women over 40 (1)

sweater | pants | shoes | earrings

While there might be a few trusty formulas for simple, chic, and comfortable outfits out there, finding interesting and subtle ways to switch things up can sometimes be tiring.

The truth is, something as simple as a color or a small accessory can play a big role in freshening up a recurring look – and that’s exactly what you see here!

Start with these wide-leg pants – featuring pleats at the front and this gorgeous deep brown shade, these trousers are the perfect go-to closet staple with their simple design and elevated material. 

On top, pair your pants with this alpaca crew – another timeless cozy sweater style that you can reach for any day of the week for a flawless choice. Featuring a relaxed fit with design details like a high neckline and slightly tapered sleeves, this sweater is a true classic for any time. 

For accessories, blend the classic and the contemporary with a pair of strap ballet flats that follow the color palette of the trousers. Opt for the rectangular wide hoop earrings for a slightly unexpected touch, bringing in a gorgeous touch of silver to spice up the look. 

8. satin top + drape pant + slingback pump + leather tote

outfits for women over 40 (7)

top | pants | pumps | tote

Monochromatic-inspired looks can take gorgeous ensembles and elevate them even more, which is why these outfits are always a hit! The single shade used in these kinds of looks draws attention to other elements of the outfit, which is why I love to bring in pieces that contribute plenty of visual interest to the final result. 

This satin top does just that, bringing in a beautiful draped effect. Paired with its high neck design, this top is an ultra-elegant piece with a relaxed fit for added comfort.

Pair with these light, neutral drape pants on the bottom. Also beloved for its fit, these trousers play off of the texture of the top while containing the look with structure and its wide-leg fit. 

Use the accessories to tie the look together with its final touches. This stunning medium leather tote brings structure to this look, while this slingback pump keeps things refined and sleek. 

9. sleeveless midi dress + leather belt + heels + hoop earrings

outfits for women over 40 (8)

dress | belt | shoes | earrings

Yet another perfect transitional piece that’s perfect as we inch closer to the transitional months between winter and spring. Whether you find yourself in predominantly cold or hot weather, this sleeveless midi dress gives up plenty of styling options that can easily adapt this piece to wherever we are.

For this particular look, simple is the way to go. Pair your dress with a simple, skinny Italian belt for definition as it flairs into an a-line skirt at the bottom. 

On top, balance out the gold hardware of the belt with some small hoop earrings for a delicate touch, and finish off with this simple, ultra-comfortable pair of block heels you won’t want to take off all day long!

10. high-waisted jean + pullover sweater + flats + metallic earrings

outfits for women over 40 (9)

jeans | sweater | flats | earrings

If you have been following my page, you know I just love the way French women tend to dress, as well as the principles behind their style. Rather than hopping on all of the current trends, French fashion tends to have a far more timeless appeal – classic pieces that stand the test of time, effortless styling, and chic ensembles that make for the perfect addition to any closet. 

For this more casual look, start with a pair of classic jeans. Featuring a slightly shorter length and a traditional silhouette, these trousers also feature a high-rise fit for even more flattering results. 

If you are looking to step out of your everyday neutral palette without overdoing it, then this rolled-neck pullover sweater gives you a subtle pattern and pop of color while still remaining elegant and understated.

These small hoop-shaped earrings give this look a final polished touch, while these basic flats square toe flats add a more modern – yet still timeless – flair. 

Want a cheat sheet to mix and match casual pieces with elegant style? I have a free checklist, among other freebies, that you can get by signing up here!

11. satin slip skirt + silk top + pumps + stud earrings + handbag 

outfits for women over 40

skirt | top | pump | earrings | bag

Playing off of another staple, this look bases itself on a classic black satin slip skirt. Its sleek silhouette forms the base of this outfit, while the fabric provides flowy movement and texture. 

On top, a silk top matches the feel of the skirt, making this outfit feel elevated and cohesive. Paneled construction on this top results in stunning, intentional stitching detail that makes for a special touch, while the shirt itself features a relaxed fit to keep you comfortable and at ease wherever you’re headed. 

Pointed-toe kitten heel pumps add the classic shoe this outfit calls for, while still being realistic to wear. Other accessories work to further elevate this look with their subtle, classic touches.

Accessorize this outfit with a fabulous bag to finish off this already-fabulous look. This tweed bag brings extra style points, adding some subtle color and structure to the look as a whole.

For earrings, these cubic zirconia studs are the perfect way to bring it all together with understated elegance. 

12. midi slip skirt + cashmere top + knee-high boots + earrings + wristlet

outfits for women over 40

skirt | top | boots | earrings | wristlet 

For those looking to add a bit more color or patterns to their looks, this outfit is a great way to do it! By blending the timeless silhouettes we know and love with some fun use of animal print and patterns, we can create an amazing classy outfit for your week.

Start with this midi slip skirt, featuring a small playful yet classic pattern that brings depth and movement to the piece. Made from textured fabric, this pull-on skirt is comfortable to put on and wear throughout the day. A side slit brings even more functionality and style at the same time.  

Pair your skirt with this cashmere top. A subtle but effective padded-shoulder detail brings elegant structure to this piece, while a mock neck detail continues to elevate it even further. 

A pair of knee-high boots make for the sophisticated touch known around the world, while a pair of teardrop stud earrings introduce a touch of modernity and felinity to the ensemble. 

For your last accessory, this leather wristlet is ideal for carrying your essentials as you slip out the door, all while adding an elegant dash of personality – and a little edge – to your look.  

13. satin top + wide-leg jean + mules + drop earrings + leather shoulder bag

outfits for women over 40

top | jeans | mules | earrings | bag | cardigan

Begin this last look with this satin top, a truly versatile number that can be worn with pants and skirts alike. Even if you want to stray from the neutrals, integrating different colors can be overwhelming if you don’t usually go that route – but no need to stress! The trick is to start small.

Infusing a dash of color while keeping things sophisticated and fun, this top also drapes beautifully featuring a v-neck detail and a relaxed fit. Paired with a long cozy cardigan, the contrast of fabrics and styles creates a stylish combination that also feels wearable, whether you wear this to a coffee date or brunch.

On the bottom, donning a pair of vintage wide-leg jeans brings balance to the outfit as a whole, while also working to elongate your figure with its high waist fit and supportive design. Besides being of great quality, these black pants are undoubtedly going to become a go-to piece for your closet rotation. 

For shoes, a pair of heeled mules brings the perfect balance of comfort and class while straying from the traditional pump, and a black leather shoulder bag brings weight and dimension to this outfit. 

A pair of gorgeous green drop earrings ties in the outfit with a similar color palette to the top, finishing things off with a polished, feminine flair.

Defying Age With Elegance With These Outfits for Women Over 40

From dressing for special occasions to nailing your new styles and even forming your individual style personality (and casual wardrobe!), there are plenty of great things that can come out of embarking on your fashion journey. I stand strongly behind the principle that the most stylish women have one thing in common: their confidence! 

More than being about the way you look, fashion is about feeling empowered in all of the best ways, from aiding our self-esteem to helping us figure out exactly who we are or want to be. After all, great style is about so much more than a certain clothing item, your body type, or your age. 

Another way to ensure you have great style is by focusing on timeless, investment-worthy pieces. Wondering what those are? Keep reading: 6 Investment Pieces To Have by the Time You Turn 50


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 mychicobsession.com 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.