Weekend Casual Style for Women Over 50: 3 Outfits That Feel Easy and Polished
Weekend Casual Style for Women Over 50
Weekends are made for slowing down a bit, running those “just a few things” errands, and maybe even grabbing a coffee or brunch with a friend. I like to have a few outfits that look pulled together without feeling like I’m trying too hard, and these three are exactly that. All of the clothing I’m wearing in today’s post is from Chico’s, and I’ve styled each look with accessories from other retailers that you’ve probably seen me use before. Whether you’re heading out the door or staying local, here’s how I’m keeping things comfy but cute.
Easy, Breezy, and Ready to Go – White Shirt and Denim Shorts
This look is clean, classic, and fuss-free. A crisp white sleeveless shirt paired with dark denim shorts feels fresh and cool, even when the temps start to climb. The structured top balances out the relaxed shorts, and the neutral flats give it just the right amount of polish.
Why it works for the weekend: It’s the kind of outfit that’s perfect for running to the farmers market or meeting a friend for iced tea. You’ll stay comfortable, but still look put together enough for an unexpected photo or if you run into someone you know.
Style tip: If you’re not a fan of sleeveless, you can easily layer this with a lightweight cardigan or denim jacket for more coverage. Add a statement earring or a colorful bag to bring in a little personality.
Sleeveless Shirt
This Sleeveless Shirt is made from crisp cotton poplin, and it feels like one of those classic pieces you can always count on. The fabric has just enough structure to look polished, but it is still lightweight enough for warm days. The high-low hem is a nice touch, especially if you like a little extra coverage in the back. It buttons all the way up and has a clean, collarless neckline that looks great on its own or layered under a cardigan or light jacket.
It is great to wear alone, and looks fabulous under a blazer or caridgan. This one is limited in some sizes, but this one gives the same vibe.
Denim Trouser Shorts
These Denim Trouser Shorts are just easy. The dark wash makes them feel a little more polished than your typical cutoffs, and they hit at just the right length, long enough to feel covered, but still great for warmer days. The fabric has some stretch, so they move with you instead of digging in. These are the kind of shorts you’ll reach for over and over again, whether you’re running errands or just relaxing on the porch with a cold drink.
Canvas bucket bag
This Canvas bucket bag is the perfect mix of casual and polished. I love the natural texture of the canvas paired with the faux leather trim, it gives it that laid-back, summery feel without looking too beachy. The shape is roomy enough for your essentials, but not so big that it gets heavy on your shoulder. The crossbody strap keeps your hands free, which is always a plus when you’re out and about. It goes with everything from shorts and sandals to casual dresses, so it is one of those bags you’ll find yourself reaching for again and again.
Woven slingback pointed-toe flats
These Woven slingback pointed-toe flats are such a cute and comfy option for spring and summer. They have that airy, textured look that feels perfect for warm weather, but the pointed toe gives them a little extra polish. The neutral color makes them super easy to pair with just about anything in your closet. These are great for days when you want to skip heels but still look pulled together.
When You Want to Look Chic Without Trying Too Hard
This one might be my favorite, because who says a weekend look can’t have a little structure? The matching striped blazer and shorts make a fun statement without feeling stuffy. I added a basic white tee and a belt to keep it casual, plus a pair of neutral sandals and my favorite woven bag for texture.
Where to wear it: This would be great for brunch, a casual meeting, or even a day of sightseeing on vacation. It’s relaxed but intentional.
Style tip: If you want to tone it down even more, skip the blazer and just wear the shorts with a tucked-in tank. The great thing about this look is that it can be dressed up or down.
Striped Denim Jacket
This Striped Denim Jacket adds just the right amount of structure to any outfit. The tailored fit and lightweight fabric make it ideal for spring and summer, and the vertical stripes help elongate your silhouette in a really flattering way. It looks polished without feeling stuffy, and it layers beautifully over everything from tees to tanks. I’ll wear this jacket with a pair of jeans or white pants for more versatile looks.
I wore a white girlfriend tee that is soft and lightweight with a relaxed fit underneath the jacket. It’s simple but not sloppy, and the slightly fitted shape keeps it feeling polished even on casual days.
Nautical Striped Trouser Shorts
These Nautical Striped Trouser Shorts are such a fun twist on denim. The tailored fit and vertical stripes give them a crisp, polished look, but they’re still soft and comfy like your favorite jeans. The front pockets and trouser-style waistband elevate them just enough, so you can easily dress them up or down. I love how they work with a simple tee, but you can also pair them with the matching blazer for a coordinated, put-together vibe.
To finish off the look, I added a pair of Strappy Cork Sandals that bring a breezy, natural feel to the outfit. The subtle gold accents on the sandals tie in perfectly with the gold-tone buckle on the brown leather belt, which adds a nice bit of contrast and pulls the whole outfit together with a polished finish.
Brahmin Satchel
This structured satchel from Brahmin adds a touch of sophistication with its rich texture and classic shape. It holds everything you need for a day out and instantly makes any outfit feel more polished.
The One-and-Done Dress That Never Lets You Down
You can never go wrong with a good chambray dress. This one has a shirt-style collar, rolled sleeves, and that easy button-front detail that always feels timeless. It’s soft, flowy, and hits at just the right length, not too short, not too long.
Why it’s a weekend winner: You could throw this on and be out the door in five minutes. It’s ideal for shopping, lunch out, or even just feeling a little more pulled together at home.
Style tip: Belting it at the waist provides a different silhouette. You can also wear it open over a tank and white jeans for a casual duster-style layer.
Chambray shirt dress
This chambray shirt dress is one of those one-and-done pieces that always looks good. The dress comes with a belt from the same soft chambray fabric, but I didn’t add it to keep the dress looking relaxed and oversized. The button-front and shirt collar give it that classic touch, and the length is just right; it’s polished enough for lunch out but still casual for weekend errands. It’s a perfect grab-and-go dress for spring and summer days.
Heaven Mayhem Jewelry
The Julia Gold Glass Bead Statement Necklace and Mini Knot Mixed Metal Earrings were a gift from Heaven Mayhem, and they’re such beautiful pieces. The necklace adds a soft shimmer that layers perfectly over a simple tee or dress, and the earrings have a fun, sculptural shape that gives the whole outfit a little extra flair. The earrings aren’t heavy, and they don’t tug on my ears.
I also like the GAIA PENDANT and matching GAIA EARRINGS. Heaven Mayhem’s jewelry is striking and makes a statement. You might see “similar” items to these, they say that imitation is the great form of flattery. Lol! They graciously gave me a code for you, use code STEPHENS15 for 15% off.
Wide elastic belt
I wanted to show you the look of the dress when belted, so I added one of the wide elastic belts from the 4-pack Amazon set to give it a little more shape. The stretchy band is super comfortable, and the vintage-style buckle adds a fun, polished touch. It’s an easy way to switch up the look of a simple dress and make it feel a little more styled.
That wraps up my weekend casual picks, and I hope they gave you a little style inspiration. These looks are great for running errands, grabbing lunch, or just enjoying some downtime. It is always smart having a few easy outfits on hand makes getting dressed feel a whole lot simpler. Let me know which look was your favorite, or tell me what your go-to weekend outfit is these days. I always love hearing from you!
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Verse Of The Day
John 13:14 (NIV)
14 Now that I, your Lord and Teacher, have washed your feet, you also should wash one another’s feet.
found it… love the dress/outfit 🙂
😊 All cute
😊 cute purse
Found it 🙂 The chambray shirtdress is so versatile!
OH MY GOODNESS! I finally found one of your 🙂!! I don’t always click on each post due to time constraints, but glad I did pick the post I did today! Love reading and seeing your posts each day!!
I love the versatility of the denim dress! 😊
🙂My favorite is the denim midi dress.
🙂 Found it! I love the Brahmin satchel.
:)love the denim dress. Looks so comfortable.
😊
I love the shirt dress on you. I wish I had the confidence to pull it off. I tried the oversize look and I felt like I looked like I was back in maternity wear.
🙂 the bucket bag is adorable
😃I love the look of the belt added to the shirt dress.
I loved today’s post. The belts are ordered and I already have the denim dress. I was concerned that the sleeves wouldn’t give enough coverage and they didn’t. However, if I unroll them they are just right. I think I’ll wear it to Sunday brunch tomorrow.
Found it! :}
🙂 I like the bucket bag!
🙂 Cute outfits. I like wearing a tee shirt dress with sandals or a casual pair of linen pants with a tee shirt or tank with linen shirt worn as a jacket. All easy, quick and simple.
😃 What a great picture of you and Joe! I really like the chambray dress and think it would be so versatile.
🙂 the belt looks good with the denim but I struggle with belting denim dresses on me.
🙂 The stripped short suit is perfect I think for church or going to dinner, I live in California so usually anything goes.
Great outfits 😁
🙂 Great options for casual weekends!
🙂 found it
I had to laugh at the first outfit – sleeveless white button up shirt and jeans shorts. That was my uniform for more years than I can count growing up in Florida and then a busy young mom raising my babies. Still a favorite look. Love the green stripe outfit. Wow what a statement.
😀 The first outfit I like the best. Easy, breezy for a hot summer day. The Discovery travel set looks amazing! I need to look into it.
found it!
love that striped outfit!
Love the denim dress, as well as the striped shorts and jacket. They look great on you! 🙂
Cute slingback. 😊
😊 i love the chambray shirt dress!
🙂 Found it !!!
:). I still luv the striped blazer and shorts. So different! I would never have thought to wear a brown belt with it but you make it work.
🙂 found it. Denim shorts are my go to for casual summer dressing.
😊
The picture of Joe & you is so cute!
😊
The picture of Joe & you is so cute!
🙂 Denim dress with the belt looks great!
Found it!☺️
I love the denim dress!
😊 I like the chambray dress, belted. As a petite, that’s how I would wear it.
😀 Found it. Really like the denim dress.
😊. The chambray dress looks comfy and adding the belt dressed it up!
😊 I love the striped jacket and shorts and the Chambray dress!
😀cute
😃 definitely more my style
🙂 Found it
I am a little confused about the Denim Trouser Shorts. When I click on the link it shows zipper & button closure instead of pull-on.
UGH! I was struggling, and described the wrong pair of shorts.
NP
🙂 Those woven slingback flats are adorable and a great price too!
Love, love, love the striped shorts and jacket.
🙂
Love the denim dress with the belt.
Found it! 🙂 Love the purses, I am sucker for purses! I am needing a new pair of denim short and those are really cute that you modeled!
Found it! Love the purses, I am sucker for purses! Need to get a new pair of jean shorts those are cute you modeled!
I found it. 👗👗👗😀😀😀😀
🙂 denim is always a winner.
😀didn’t find it I like the trouser shorts
Found it 🙂 Love the striped outfit!
Love these ideas! Denim and white is always a great choice! Found it!:)
Found It.
🙂 I like the blazer & trouser shorts outfit. I also bought the 4 belt set quite some time ago. I have used them so much!
Hi Tania,
I love your style! You posted a photo on todays post (5/12/25) of you and your husband and I have searched (IG, pinterest, youtube and on this post) for the link to the top you were wearing…but I am unable to find it, can you help? Also, I am wondering if you have talked anywhere about your weight loss, I’ve been following you since we were all locked up…And your hair, I love how it is cut, should I just say, you have great style and I am trying to be a copycat?? :)). Keep up the great work – God is using you !! Love your God notes and scripture too.
I’m going to be showing the top in a future post, but here’s the link for you: https://bit.ly/4j0hub5
😊Love the striped shorts and blazer.
I like all three outfits but I like the belted denim dress best. found it. ( :
😊
The denim dress is my favorite.
Found it
🙂 Love the sleeveless white blouse at the beginning of the blog.
Always love your casual outfit choices! I live in casual tops & denim shorts in summer… And I ordered that same canvas bucket tote from J.Crew week before last. (Got it on sale for $29!😁) It’s smaller than a “normal” canvas tote and much cuter, too!
Love the bucket canvas bag and sling back shoes! 🙂
I love the belt. with 😊. The dress is too dark denim for me. Striped outfit is the best in my opinion. Love Chico’s.
Love the belt! Found it.
🙂 LOVE the denim dress! You are right, you just can’t go wrong wearing this!
Happy Mothers Day!
Beautiful family picture! Have a wonderful Mother’s Day
🙂 Been thinking about that chambray dress too. How wide is that belt? Might be too wide? BTW, I like the updated font.
I’m glad you liked the font. No one else has mentioned it, so I figured it was alright. The belt is probably 2″ – 2 1/2″ wide.
Love the sling back flats!🙂
The dress looks so cute belted with the straw handbag – very chic!
🙂. Love the striped jacket and shorts!
🙂 I like them all. Especially the first one.
I love the stripe jacket and shorts outfit. You look great in it. It’s late now so I didn’t even look for smiley. I couldn’t find him in the lip products yesterday either.
😀 cute purses .
Really liked the striped blazer and shorts set.
😊 like the denim dress with the wide belt.
😃 I really like the denim dress and how you styled it! HAPPY MOTHERS DAY!
😊
That denim dress looks so comfy.
😀 great post!
😊 Love the denim dress
😊found it
Comfortable looking clothes
🙂 like the denim trouser shorts
😊I like the styles. Thats me in the chambray shirt dress with the belt. Love it!
🙂 Like them all
Cute outfits – especially the first one. 🙂 found it!
😀 Love the nautical look
😀 found it
😊 I like all those outfits you styled. Wearing a belt on the shirt dress makes a big difference – more polished looking but still cute and fun.
🙂 Like them all!
I found it.
🙂 cute shirt dress
😊 love the shorts and blazer outfit! Adorable 🥰
The belted chambray dress is my favorite and no wonder that it’s from Chico’s. Found it! ☺
🙂 I’d be wearing that denim dress on repeat.
I never really look, but I saw it! I love the wide stretch belts and wear one with the same denim dress. For once, I beat you to buying before you did your “showing”.
😊The first shorts outfit is perfect for farmers market and I also see it at the plant nursery with sneakers or a casual sandal. I took advantage of the Chico’s sale today.
🙂 You really do wear it all so well !!!
😊 I like the striped blazer and shorts!
🙂
Nice! I love the denim dress, I can see this as a very versatile piece.
🙂 You wear it all so well !!!
🙂 I love the striped jacket and shorts!
😀 Love the striped jacket and shorts!
🙂 All these outfits look amazing!! I especially like the striped blazer with the matching striped shorts. So unique. And the denim dress is really great as well.
Thank you for all your work rounding up week end sales and specials.
🙂 Found it! You look fabulous in the striped shorts and jacket!
🙂 I like the 1st outfit. Simple, yet looks great. I like the dress when you add the belt.
😊 I like all the outfits but especially the pinstripes!
Are the cork sandals real comfortable and walking friendly?
The first time I tried them, they hurt me a little across the top of the foot. But, not I don’t notice that, so I must have broke them in.
😊 The denim dress is so cute.
😀love the denim dress!
Stephanie
🙂Love the denim dress an elastic belt combo . So easy and chic. Any denim dresses above the knee, midis tend to make me even shorter than I am?
😊Love all the outfits!! Especially the striped denim jacket and matching shorts.
FOUNF IT! 🙂 That stripe short set is so cute and the chambray dress looks so comfortable! You make all these clothes look so cute and stylish!
Okay, funny placement of 😀
🙂 You wear it well
Found it. 🙂 The dress is cute.
☺️ Love all these outfits. I especially like the dress when you belted it. Such a smart look!
☺️ on your wide elastic belt
😊love the denim dress with and without the belt.
😀Found it! I like the chambray dress!
😊 those nautical striped shorts are super cute!
also FOUND IT
Love the denim dress☺️
:} Love the outfits!
🙂 A shirt dress is always a winner.
😊 Thanks for showing us these great options!
😊 In the cute chambray dress, why did you size up? Is that what you’d recommend for everyone?
I sized up because I knew I wanted the oversize, flowy look. If you plan on wearing the dress belted, then you usual size should work.
🙂 Great post! Love the dress with the belt and the shorts and jacket set!
😊 Love the striped suit combo
🙂 Love that sleeveless top–unfortunately, they’re all sold out except XL.
🙂 I like the denim dress. It really is a one and done summer or even fall outfit.
😊 found it! I love the pinstripe jacket!!
😊 all th summer outfits look great.
Found it. Love Chicos, I rarely leave the store empty handed!
I love the dress!!! super cute belted! No shorts for me, but they look great on you…Happy Saturday❤❤❤
I’ve had my eye on the denim dress for awhile. I love it! 🙂
Cute Outfits ☺ Found It..
😀putting that belt on the dress made it look like a totally different dress!
Love all the styles but that chambray dress is the best !
Do you think you really need to size up
Can’t decide the size
Jayne, I sized up to make sure it would be oversized. My usual size would have probably worked, but I love the flowy oversized look.
Well it looks beautiful on you
Thank you
🙂 I feel like denim never really goes outa style, is that true of just me?
the dress looks great!
found it!
I really like the striped blazer and matching shorts.
🙂 Like a seeing the nice casual look.
Love the denim dress 🙂 found it
🙂 Love the jean shorts (my kinda length) and the white crisp shirt!
🙂 Love the Chico’s dress!
Have a very blessed Mother’s Day!!
😉 Love the dress,
🙂 Like all these looks and you look great in them.
😊 All cute outfits. The striped jacket and shorts outfit is so smart looking!
Sleeveless is my go to! 🙂 Belts are in the cart, exactly what my summer dresses have been missing.
🙂 Found it. I love the white shirt–are the armholes large? I want to order it.
Ordered the chambray dress!!!
No, the arm holes weren’t oversized.
Love the trouser shorts. They look so comfy. 😃
☺️ the shoes are cute. The dress is cute with belt.
Found it
liked the chambray wide belted dress
I been just wearing different colored t shirts with a long sleeves light shirt over it because it’s getting hot here.
I wear straight jeans.
🙂
Love the denim dress with the belt!
Love a good denim dress. Found it!
Found it! Love the crisp white shirt.
😊 Cute outfits…Love the denim dress!! Have a great weekend!
😀love the denim dress and the necklace is beautiful
😀 cute outfits! Love the basic white shirt and denim shorts.
Found it 😀
Love all the outfits especially the striped blazer and shorts…looks amazing on you!
🙂found it! Great easy outfits!
: ) Cute!
I really like the chambray shirt dress.
I ended up wearing it all night long. It is soft and almost like wearing a robe, but it looks much nicer. Lol!
😊
Love the outfits. Especially like the dress. I wouldn’t have liked it if I saw it online with the belt, but I do like the way you style it.
I like wearing my shirtdresses loose and flowy. I sized up to a size 2 instead of my usual 1 to make sure it gave me the oversized look.
🙂 You look fabulous in all these outfits!!
🙂 found it. I love the denim trouser shorts.
I really like all three! I have a similar dress so a belt would change it up nicely.😁
🙂 The jacket and shorts set is cute!
Found it.
😀 that Brahmin purse is divine! Hope you kept it!
Of course I did! Lol!
🙂 I like leveling up my outfit when I go out, even though I live in an area that’s tshirt and jean shorts/leggins.
🙂 Love the striped denim jacket!
FOUND IT🙂! This post was worth the wait. Love the white sleeveless shirt with the denim shorts as well as the striped denim shorts & jacket! Actually I like everything you presented.
Found it 🙂Cute outfits!
😊 Thanks for the weekend sale info! I love all denim! I have so many variations but I love this dress!
😃
I love the bucket bag and the wide belts. I have already put the wide belt in my cart.