classy casual outfits women over 50

14 Classy and Casual Outfits for Ladies Over 50

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As we get older, I think it’s safe to say that most of us forgo paying as much attention to current trends and care more about looking put-together, classy, and dressing in our own style preferences. But when it comes to dressing classy in more casual settings, that can be easier said than done! Older women are so often relegated to certain styles, patterns, and colors when it comes to what’s shown in magazines, TV shows, and marketing. That’s why I’ve put together 14 classy, casual outfits for ladies over 50. These casual outfit ideas will have you feeling your best, no matter if it’s a special occasion or just everyday wear.

1. tunic top + white pants + mixed metal watch + woven mules

classy casual outfit for ladies over 50 - linen pants tunic top mixed metal watch woven slides

top | pants | mules | watch | hoops

A great pair of white pants is a spring and summer staple. No matter your preferred fit of pants, a pair in white is the perfect way to brighten up your favorite looks in warmer months. They’re also a great way to add contrast to your looks when paired with a bright color, or one in a darker shade.

Start this casual, chic look with your pair of white pants. These straight-leg pants are made with a stretch linen blend, meaning that not only will they be flattering, but they’ll be comfortable for wherever your day takes you. Whether your day involves a busy day at the office, taking care of grandkids, or spending a Saturday with friends, these will make sure you are chic but comfy the whole day long.

Next, add a popover tunic top. Tunic tops are a flattering piece for any body shape or body type and are the more casual sister of the classic button-down. For shoes, try this pair of woven mules. The woven material will help keep you cool even in the warmer summer months!

When it comes to casual yet classy looks, sometimes simple is the best way when it comes to accessorizing. Finish this look with gold hoops and a versatile mixed metal watch.

2. blazer + striped tee + wide-leg jeans + sneakers

classy casual outfit for ladies over 50 - striped tee oversized blazer wide leg jeans

sneakers | tote bag | jeans | striped tee | black blazer | sunglasses

If you’re ever in doubt about how to add a classy touch to a casual look, try a blazer! A longer, slightly oversized black blazer will be your best friend. The longer length will help elongate your body, whereas the ones that stop at your waist often end up dividing your proportions in two.

The base of this look is familiar to many of us. A striped short-sleeved tee is a capsule wardrobe staple, and a flattering pair of straight-leg or wide-leg denim jeans offer the perfect balance to your look.

Shopping List for Your Capsule Wardrobe: Need ideas of what to actually include in your capsule wardrobe? Whether you’re updating your closet for spring or starting from scratch, MCO has a free resource library you can access here!

A leather tote bag, sunglasses, and white sneakers complete the look that’s comfortable, chic, and casual for everyday wear.

3. white button-down + linen pants + woven slides

classy casual outfit for ladies over 50 - white button down pull on pants gold jewelry

top | linen pants | earrings | bangle | sandals

Linen pants are the perfect piece to create a classic look for a casual outing. Create a stylish look by pairing them with a more structured top, like an Oxford button-down shirt, to create balance in your outfit.

Where you can really elevate this look is in your accessories. A pair of gold hoops and a gold bangle will help to set your look apart. Jewelry is also an opportunity to bring your personal style into a classic outfit formula. Finish off the look with a pair of comfortable sandals.

Related: Styling a Classic Linen Outfit: My Mom vs Me

4. white tee + button vest + skinny jeans + ballet flats

classy casual outfit for ladies over 50 - sunglasses sweater vest skinny jeans white t-shirt ballet flats

white tee | skinny jeans | ballet flats | sweater vest | sunglasses

A classic white tee starts this next look. One tip that I like to use when creating casual looks that are still classy is to start with an inspiration look on the more elevated side, and then add in more casual pieces to make it fitting for everyday wear.

For this style, start with the idea of an elegant, classic suit. You have your staple black vest and jacket, and a white button-down underneath. Break this look down by removing the jacket to focus on the vest, and swap out the button-down for a white tee.

Next, medium wash or dark wash denim skinny jeans pair well with this look to create a more casual spin of a classic suit look. Black ballet flats complete the style.

5. knit sweater + trench coat + straight-leg jeans + ballet flats

classy casual outfit for ladies over 50 - trench coat knit sweater jeans ballet flats

jeans | bag | flats | trench coat | sweater

Classy, casual outfits for ladies over 50 are the perfect opportunity to pair together pieces from your capsule wardrobe. Creating chic, tailored looks doesn’t have to be difficult – choosing well-fitting, elevated basics is a great way to create an outfit that you’ll feel confident in.

For this look, start with a pair of wide-legged or straight-leg jeans with no holes or rips. Next, a quality knit sweater, like this alpaca crew from Everlane, will pair well with your jeans. Everlane is a great place to shop for quality basics at an affordable price.

If you don’t have a trench coat in your closet, spring is the perfect time to add one to your wardrobe! They’re the perfect Parisian staple, and there are so many ways to style them. A structured bag acts as your pop of color in this look, and classic flats complete this outfit.

6. striped cardigan + white tee + black midi skirt + mary janes

classy casual outfit for ladies over 50 - midi skirt white tee striped cardigan tote bag

midi skirt | mary janes | white tee | striped cardigan | tote bag | earrings

Midi skirts are the perfect solution if you’re searching for an elevated piece that is as comfortable as it is flattering. They are typically slightly more casual than a maxi version, but offer more coverage than a mini.

The classy portion of this look is provided by the satin material of the skirt, while a white tee and striped cardigan act as the more casual elements. Gold square hoops, a black leather tote bag, and Mary Janes provide the perfect accompaniment for your base. This would also be a great look to go into the office!

7. linen barrel pants + denim jacket + t-shirt + white sneakers

classy casual outfit for ladies over 50 - denim jacket linen pants white tee sneakers

denim jacket | pants | sneakers | white tee

A denim jacket is a great way to complete a casual yet classy look in warmer months. It’s easy to take on and off, neutral enough to pair well with many colors and looks, and slightly structured while still being comfortable.

This is another look with a white tee as a base. The perfect white tee isn’t see-through, washes well, and acts as the perfect foundation for outfits year-round. Next, add a pair of linen pull-on barrel pants. Pull-on pants are comfortable and offer plenty of range of movement, and are the perfect “soft” element to balance the structured look of your denim jacket.

Clean white sneakers complete the look, perfect for those days when you’re on the go but still want to look put-together.

8. shirtdress + woven tote bag + sunglasses

classy casual outfit for ladies over 50 - linen shirtdress sunglasses straw tote

dress | sunglasses | sandals | woven tote

Your favorite little black dress doesn’t have to be reserved for formal occasions! In fact, I argue that everyone should consider having at least two little black dresses in their closet – one casual, and one elevated.

Choosing a little black dress in a shirt dress style is a great way to transition from work to play. Plus, this version has pockets, which is always a bonus. Accessories play a big role in this look, as the versatile piece can easily be dressed up or down. Leather slides or your favorite comfortable sandals, a woven tote bag, and tortoiseshell glasses are the perfect way to create the perfect classic summer outfit.

9. cardigan + skinny jeans + mule slides

classy casual outfit for ladies over 50 - red cardigan skinny jeans leather mules

cardigan | skinny jeans | mule slides

Don’t be afraid of bright colors when it comes to creating classy, casual outfits for ladies over 50. Adding a pop of a statement color, like the red of this cardigan, is a great way to bring your personal style into a casual look. Wear this cardigan as a buttoned top, or layer it over your favorite tee or striped top.

Next, add your favorite pair of skinny jeans and a pair of leather mule slides. If you prefer a looser fit of jeans, almost any style is interchangeable with this look!

10. knit crewneck + round sunglasses + wide-leg jeans + ballet flats

classy casual outfit for ladies over 50 - cashmere sweater jeans straw tote sunglasses

ballet flats | flare jeans | straw tote | crewneck sweater | sunglasses

Little details make all the difference when it comes to putting together the perfect casual look. For instance, the ribbing and slightly cropped fit of this cashmere sweater offers the perfect balance to a pair of high-waisted jeans, with a lined hem on the cuffs.

Complete the look with leather ballet flats with a bow detail, gold-rimmed sunglasses, and a straw tote.

11. collared shirt + white midi skirt + Adidas spezials

classy casual outfit for ladies over 50 - white midi skirt button down basket adidas spezials

sneakers | midi skirt | top | woven bag

Another great rule of thumb when it comes to putting together classy and casual looks is to try mixing aesthetics to create interest in your outfit. This combination plays with traditionally formal and athletic features to create balance.

First, start with a white midi skirt. This skirt offers lots of movement, while the length is flattering in terms of providing coverage while still allowing you to make a statement with your shoes. In this case, the shoes are the Adidas Spezials! This shoe is perfect for an active day, whether it’s walking around a farmer’s market, the city blocks, or maybe attending a sporting event.

Next, a blue button down with a frilled, rounded collar is the perfect way to add a bit of structure to this look. A woven basket bag is the finishing touch, whether it holds your favorite book, a snack, or your other daily essentials.

12. navy button-down + tank top + dress shorts + sandals

classy casual outfit for ladies over 50 - trouser linen shorts tank top button down

dress shorts | sandals | bag | tank top | button-down shirt

If you’re unsure of how to put together classy outfits with shorts, try a pair of trouser-style dress shorts. This linen pair will help you stay cool, while still achieving a sophisticated look. Next, a similar-colored tank top can be tucked in to elongate the shape of your body. Add a belt to further create a flattering form!

On top, try a navy button-down shirt. Depending on your comfort level (and the temperature) you could leave this open, or button it partially. For accessories, try a two-toned crossbody bag, and leather sandals to tie it all together.

Related: Fight the Frump: 12 Easy Ways You Can Fix Your Frumpy Outfits

13. flare jeans + collared sweater + square earrings + gold sandals

classy casual outfit for ladies over 50 - wide leg flare jeans popover sweater gold sandals

top | jeans | sandals | square hoop earrings

A cohesive metal choice can really tie together a casual look. Elevate this outfit by incorporating hints of gold throughout, which makes your choices look more intentional.

Knits in quality fabrics make all the difference. This soft sweater with gold buttons is the perfect way to make a statement while still being neutral. Pair it with flared pants to mix up the more typical styles of denim. You could also swap these out for boot-cut jeans to achieve a similar look.

Add gold woven sandals to make this look date night-ready. Vibrant hues like gold will set you apart from the crowd! Gold hoops continue the theme, and the square shape of these makes for a unique style.

14. lady jacket cardigan + trousers + sunglasses + flats

classy casual outfit for ladies over 50 - lady jacket cardigan wide leg pants tote bag

cardigan | mary janes | trousers (similar) | tote bag | sunglasses

A lady jacket is a timeless way to add a touch of sophistication to classy, casual outfits for over 50. Lady jackets come in all different styles, and in this instance, our lady jacket takes the form of a cozy cardigan. If you’re looking for an alternative to bold prints, stripes are a chic way to add a pattern to your outfit.

Next, swap out jeans for a pair of wide-legged trousers. These will elevate your look, while still being comfortable and practical. Khaki or white pants perfectly complement the colors of the sweater, while still going a long way in your capsule wardrobe due to their neutral colors.

Finish the look with Mary Janes, a leather tote bag, and tortoiseshell sunglasses.

Feel Your Best at Any Age With These Classy Casual Outfits for Ladies Over 50

Age is just a number, and it doesn’t have to determine what you’re limited to when it comes to personal style! Casual, chic pieces can be worn at any age, and hopefully taking inspiration from the looks above will help you to put together combinations of outfits that are not only comfortable and flattering, but also help you to feel put together and chic in your everyday life. You don’t have to wait for a special occasion to feel put together and elegant!

Did you love the jean outfits in this post, and want more ideas on how to style them? Up Next: A Fashion Guide: How to Wear Jeans Over 50


Hi, I'm Cassie! My husband and I have a full house with three furbabies, and when I'm not spending time with them, I'm loving all things fashion, travel, and romanticizing life's little moments. I'm also a self-described book nerd, and am always on the hunt for my newest read.