I was raised on the all-too familiar outfit formula of “jeans and a cute top.” Somehow, this well-known moniker was the solution to nearly any occasion. I’m meeting a friend for a glass of wine, what should I wear? Jeans and a cute top. Grabbing brunch with my parents? Jeans and a cute top. At its core, “jeans and a cute top” signifies the desire that many of us share to create classy, yet casual looks that are fitting for so many of our daily activities. Once you boil it down to that, you can start to get more creative and stretch the boundaries of this classic formula. Ready to learn more? Keep reading for 13 classy casual outfits for women over 40 – although these would be chic looks no matter what the number on your driver’s license says.
1. white button-down + maxi skirt + sunglasses + bangle + tote bag + flats
What occasion calls for a classy casual outfit more than sipping coffee outside a Parisian cafe? Even if you’re just visiting your local coffee shop, this type of outing is the perfect time to debut a chic look. One of my favorite ways to slow down and start my weekend in a fun way is to get a little dressed up to go enjoy a cup of coffee with my husband or friends. Doing so makes every weekend feel a little more special!
A maxi or midi skirt is the perfect way to make any outfit feel a little more classy and elevated. On top, stick to something more casual, like an oversized linen button-down. This pairing creates the perfect balance of laidback and luxe, just like jeans and a cute top. Next, add texture with your accessories. Grab a large tote bag in a woven pattern, and don’t forget a cute pair of leather flats. The best part is that you might already own similar pieces to these in your capsule wardrobe.
navy blue skirt | shirt | flats | bag | sunglasses | bracelet
2. striped button-down + crop jeans + leather bag + pendant necklace + mule slides
shirt | jeans | mules | bag | necklace
If I had to start my wardrobe over from scratch, the first piece I would replace would be a striped button-down shirt. Let me make my case: you can wear it year-round, it’s perfect for layering, and it can be dressed up for work or dressed down for a casual lunch, and nearly any occasion in between.
Have I sold you yet? If you have one hanging in your closet but don’t know how to style it, don’t overthink it. It’s the perfect base for casual summer outfits. Pair it with jeans (any color will do), a leather bag, comfortable flats, and minimalist jewelry. You instantly have a more specific outfit formula to turn to when you want to fall back on jeans and a cute top.
3. navy blouse + linen pants + belt + sandals + pendant necklace + crossbody bag
Jeans might be comfortable, but want to know what’s even better for chic summer dressing? Linen pants! Linen is more breathable, flexible, and comfortable when compared to denim. If you’re trying to beat the heat, swap out your go-to jeans for a pair of white linen pants this spring and summer.
On top, pair your white pants with a navy blouse for a classic color combination. This creates a great contrast in your look! Then, accessorize with timeless leather accessories like sandals, minimalist gold jewelry, a thin belt, and a crossbody bag.
white pants | sandals | belt | blouse | bag | necklace
4. black dress + trench coat + pearl earrings + ballet flats + leather bag
dress | trench coat | ballet flats | top handle bag | earrings
If you want to style casual yet classy looks, a great place to start is with a little black dress. The LBD is one of those timeless pieces that you never have to worry about going out of style. Plus, you can dress it up or down for a variety of different occasions.
Meeting friends for dinner this spring? Pair it with another one of my favorite capsule wardrobe staples: the trench coat. Then, add a few French girl-approved accessories to your Parisian-inspired look. Ballet flats are cute, feminine, and fun. A top-handle bag is a fun throwback to vintage fashion. And last, but not least, a pair of simple pearl stud earrings is the finishing touch on any classy look.
5. denim shirt + jeans + sunglasses + sweater over the shoulders + mules
Denim on denim looks are a great way to have some fun with your classic outfits, and align well with current fashion trends. Although denim itself is typically viewed as casual, it’s all about how you style it. First, let’s talk about the wash. A darker wash of denim usually looks slightly more elevated. Second, try to match the denim washes of your shirt and pants. This creates a monochromatic look that instantly upgrades your appearance and makes your look more streamlined.
Your accessories are also key to making a denim-on-denim look appear classier! For shoes, go for a pair of patterned or textured mules. They’re the perfect way to introduce interest to your outfit and break up all that denim. Then, on top, tie a sweater over your shoulders. There’s something about this simple touch that makes any outfit appear more elegant! Finally, finish your look with a classic pair of tortoiseshell sunglasses.
denim shirt | jeans | sweater | mules | sunglasses
6. denim jacket + jeans + button-down + neck scarf + tote bag + belt + mary janes
denim jacket | jeans | shirt | scarf | mary janes | tote bag | belt
We’re not finished with denim on denim, yet! If you love to style a casual look around a denim jacket, here’s an updated take on how you can do so in a slightly more elevated way. First, try swapping out your traditional denim jacket for a chore jacket or a lady jacket style. Or, if you love your current denim jacket, just try to make sure that you coordinate the wash with your jeans! Even better if they’re both a dark wash.
Underneath, balance the casual aesthetic with a slightly more elevated piece. A solid button-down shirt is perfect! Tuck the shirt into your jeans, and add a belt to complement your natural body shape and highlight your waist.
Finally, keep the simple color palette going with a navy tote bag (Carolyn and I both love our Longchamp bags). Add a silk neck scarf and a pair of leopard print flats. The patterns will help to make your look more interesting and intentional!
7. sweater blazer + t-shirt + pendant necklace + leggings + watch + tote bag + loafers
loafers | leggings | t-shirt | sweater blazer | necklace | tote bag | watch
There’s nothing like a cozy day spent indoors when it’s raining. On these types of days, no one really wants to reach for a pair of stiff denim jeans! If you’d much rather wear a pair of black leggings, here’s how to dress them up for a day working from home.
On top, add a basic white t-shirt underneath a soft sweater blazer. This is a classic style from J.Crew that is another great capsule wardrobe staple! It’s slightly more elevated than your average cardigan, which makes it the perfect piece to wear on any Zoom calls.
You can keep your accessories simple and practical for this look. A work bag, a classic gold watch, and a simple pendant necklace are all you need to complete the ensemble.
8. blazer + sweater + white t-shirt + baseball cap + jeans + tote bag + boat shoes
boat shoes | jeans | tote bag | sweater | t-shirt | blazer | hat
A layered look full of timeless classics is another great way to instantly elevate your appearance. If you’re going for a casual look but still want to look put together, don’t be afraid to have fun with layers and showcase your personal style. Love a certain sports team? Start your look by repping them on a baseball cap. If you’re a big fan of leopard print (us, too), add a tote bag with that pattern. Want to try out one of the current trends? Add a pair of boat shoes for a nautical-inspired aesthetic.
Keep the rest of your layers simple and classic. Jeans, a white tee, a neutral sweater, and an oversized blazer will keep you warm in transitional spring or fall weather, without having to wear a coat.
9. white skirt + cable knit sweater + earrings + necklace + watch + boat shoes
sweater | skirt | boat shoes | necklace | watch | earrings
The right accessories can make or break a classy casual outfit! If you’re trying to strike that perfect balance, try the sandwich method to match the aesthetic of your footwear to your top. Wearing a more elevated shirt with jeans? Go for a nicer pair of shoes. On the flip side, if you’re styling a nice skirt with a more casual top, try wearing more relaxed footwear.
If you’re loving the nautical vibe as much as we are this spring, try styling a fisherman or cable knit sweater with a maxi skirt. Then, add your boat shoes to balance out the aesthetic of your sweater. Keep your jewelry classy: think a gold pendant necklace, a gold watch, and gold hoop earrings.
10. polka dot dress + pearl earrings + flip flops + straw tote
dress | flip flops | tote bag | earrings
When temperatures are soaring and you want to look cute but also keep cool, try reaching for a midi dress. The longer skirt gives you great coverage, without causing you to overheat. A midi dress silhouette looks great on all different body types. Younger and older women alike rock this style and look so effortlessly chic wearing it!
If you want to wear a midi dress to a somewhat casual outing, try styling it with flip-flops, a raffia tote, and a pair of pearl earrings. It’s an easy, breezy look that you’ll want to wear all summer long.
11. sweater + white tee + white shorts + straw hat + tote bag + sandals
t-shirt | sweater | shorts | straw bag | sandals | hat
If your style personality could be described as “coastal” or “beach casual,” you’ll love this next look. Save this outfit idea for your next vacation or casual summer shopping day. First, start with a pair of linen shorts. The pleating on this pair makes them slightly more elevated than a pull-on version. Next, add your favorite white tee layered under a light sweater.
The accessories truly make this look! Leather sandals, a straw bucket hat, and a raffia-style tote bag are what make this outfit appear more coastal, and perfect for a chic yet casual summer day.
12. white t-shirt + black cardigan + jeans + sunglasses + belt + mary janes
jeans | belt | t-shirt | sweater | mary janes | sunglasses
I tend to stick to neutrals rather than bright colors, and if that sounds like you, too, try this next look. You don’t have to overthink classy casual outfits for women over 40! Well-fitting, timeless pieces often make for the best ensembles. Ignore the latest trends and stick to your favorite items. You’ll wear them with confidence, which is one of the main ingredients for a chic look!
First, start with a classic pair of jeans. Straight-leg denim is perfect for this look! Next, add a quality white t-shirt, and a black cardigan. Then, try a pair of coordinating Mary Jane flats, a black belt, and oval sunglasses for a look that’s easy, chic, and comfortable to wear all year long.
13. striped tee + crop trench + crop jeans + sunglasses + hoops + sneakers
bag | sneakers | trench coat | t-shirt | earrings | sunglasses
Last, but not least, we have a look that incorporates one of the most well-known casual wear staples: white sneakers. The best thing about white sneakers is that they can balance out nearly any elevated piece. Sometimes, real life calls for the most comfortable pair of shoes in your closet!
Style a great look with white sneakers by strategically closing quality, neutral basics. Crop jeans, a striped t-shirt, and a crop trench coat give your look enough structure to appear put together without sacrificing your effortless style. Accessorize with a chic crossbody bag, cat-eye sunglasses, and simple gold hoops.
Classy Yet Casual Style Over 40
“Jeans and a cute top” might be the one fashion formula that’s been ingrained in all of us, but there is a way to style classy and casual looks over 40 without defaulting to this one method of dressing. Whenever you’re stuck, come back to this list for inspiration. Whether you’re catching up with a friend over dinner or starting your weekend off right at the local coffee shop, you’ll be able to enjoy your outing in style!
Want to discover easy tips to look put together without overdoing it? Up Next: The Secrets to Looking Sophisticated and Stylish (Without Being Overdressed)
