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How to Elevate the Most Casual Outfits

February 8, 2024

Let’s face it. Many of us women over 50 live a fairly casual lifestyle. Whether you’re retired from your career or work from home like I do, I hear from many of my readers that they generally wear casual outfits. But those same readers tell me they still want to look pulled together and classy, even for the most casual outings or at home. Me, too! So today I’m sharing how to elevate the most casual outfits.

How to Elevate the Most Casual Outfits

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I’ve taken one of my favorite casual outfit formulas to showcase a few ways to elevate your most casual outfits. Especially in the early spring and fall, I love wearing a cozy sweatshirt with jeans and sneakers. Even over 50, this combination is a fantastic, modern outfit to wear for a really casual outing or day at home.

How to Elevate the Most Casual Outfits
sweatshirt (TTS; wearing a medium) // straight leg jeans (TTS; wearing an 8) // similar sneakers (TTS) (more economical option) // bracelet 1 // bracelet 2 // earrings

For today’s look I’ve paired my Carolina wash straight leg jeans (probably my favorite jeans in my closet!) with a super soft new sweatshirt in Placid Sky blue. Both of these items are extremely comfortable, so soft and cozy.

Tip #1 – Choose comfortable casual pieces that good quality and look “nice.”

It can be tempting to throw on something old and worn out on casual days simply because those garments tend to be the softest and most comfortable. Or maybe we think the day doesn’t warrant something pretty and special. But I say wear your nice things; don’t save them. And it’s just as easy to put on a fresh, pretty sweatshirt as it is to wear an old and faded one.


My vintage-inspired sweatshirt is just the right thickness and features drop sleeves that can easily accommodate a tee or shirt underneath. It’s listed as cropped, but at 21″ it easily covers the waistband of my high rise jeans. The sweatshirt also comes in grey, ivory, licorice (brown) and a navy and white stripe. But the sales person at J.Crew told me this beautiful blue is the one everyone is reaching for. It is such a lovely blue, and works nicely with blue denim, white, black and khaki.

Tip #2 – Consider wearing trending denim.

Now this tip is really sort of a bonus. When I was modeling these full length straight leg jeans (very on trend, but not especially “modern”), I realized I could cuff them in the ultra-modern deep-cuff fashion. Cool!

Trending Jeans Style

Yes, oddly enough, this deep, turned-up-once cuff is extremely on trend right now. I’m seeing it everywhere in the stores, and I’ve noticed some women wearing it in real life, too. I haven’t brought myself to buy a pair of jeans with this cuff sewn into them yet, and I’m not sure I will. But If you have a good pair of full length straight leg jeans you can probably achieve this look with a simple turn up of the hem. Do it just like I did: one turn up and nice and wide. If you’re really going to wear your jeans like this, I’d suggest pressing that cuff in for a more intentional look.

Trending Jeans Style

Of course, lol, I think many of us over-50 ladies have already worn this trend back in the day. But it’s made a return! Will you give it a try? Let me know in the comments. Remember, if you don’t like it, it’s not because this trend is “wrong;” it’s just because you personally don’t care for it. And that’s perfectly fine. But I love to see women our age trying new denim trends. I think it’s a smart way to look a little more elevated.

Tip #3 – Add some simple but impactful jewelry.

Even if you’re staying home or going for a hike, you can still elevate the most casual outfits with a little bit of tasteful, simple jewelry that is also impactful.

bracelet 1 // bracelet 2

I’m enjoying mixing my Lagos two-tone Caviar buckle bracelet with my multi-tone Brighton Intrigue bracelet these days. I’ve also worn my Brighton Intrigue two-tone hoop earrings.

Tip #4 – Wear a little makeup and make sure your nails are nicely manicured.

Wear Makeup and Have Nails Manicured

Obviously good grooming is essential when it comes to looking polished and put together. I’ve found that I can wear the simplest outfit, but still look a little elevated if I’ll simply style my hair and add a little makeup (even just mascara and lipstick). Keeping your nails manicured is important, too, even if you don’t wear any color.

Tip #5 – Wear classy footwear.

Generally if I’m going casual I’m also wearing sneakers. And that’s why it’s so important to have a pair or two of classy tennis shoes. What do I mean by classy? Simply that they look nice and fresh, free of scuff marks, dirt and wear and tear.

Wear Makeup and Have Nails Manicured
sweatshirt (TTS; wearing a medium) // straight leg jeans (TTS; wearing an 8) // similar sneakers (TTS) (more economical option) // bracelet 1 // bracelet 2 // earrings // London saddle bag (use code KAY10 for 10% off only at Patricia Nash)

I think it’s nice to have in your closet one pair of sharp, white leather or faux leather sneakers alone with one pair of more trendy sneakers. Personally I prefer to wear classic sneakers with full length jeans, whereas I’ll wear the more trending retro trainers with cropped length jeans. My Paul Green sneakers (similar) are several years old now, but they are super comfortable. And these Sam Edelman sneakers are a nice economical option.

Tip #6 – If you go out, carry a nice handbag or backpack.

If you do get out and about in your casual outfit, you can elevate the simple look by carrying a nice handbag or backpack. In fact, carrying a worn out bag can destroy the most elegant outfit. So get rid of any bags that have served you well but are now worn and dated.

Carry a Nice Bag
London saddle bag (c/o) (use code KAY10 for 10% off only at Patricia Nash)

Patricia Nash Designs recently gifted me this beautiful London saddle bag to share with you. They also generously gave me a code to offer you 10% savings. Lovely! You can use code KAY10 for 10% off only at Patricia Nash on any of their designs (exceptions may apply). The London saddle bag features so many wonderful compartments and pockets and, as with all Patricia Nash bags, it has a lovely, soft interior. Such a beautiful bag!

trench and bag
London saddle bag (use code KAY10 for 10% off only at Patricia Nash) // trench coat (similar)

Tip #7 – To elevate your most casual outfits, choose classy outerwear.

If you’re getting out and about, resist the urge to throw on another super casual garment on top of your outfit. Instead, opt for something a little more polished like a classy trench coat.

Classic Trench Coat
sweatshirt (TTS; wearing a medium) // straight leg jeans (TTS; wearing an 8) // similar sneakers (TTS) (more economical option) // bracelet 1 // bracelet 2 // earrings // London saddle bag (use code KAY10 for 10% off only at Patricia Nash) // trench coat (similar)

I love the juxtaposition created by combining a classic trench coat (similar) with a casual outfit of jeans, sweatshirt and sneakers. This combination is very on trend right now, so you’ll look modern and classy.

How to Elevate the Most Casual Outfits
sweatshirt (TTS; wearing a medium) // straight leg jeans (TTS; wearing an 8) // similar sneakers (TTS) (more economical option) // bracelet 1 // bracelet 2 // earrings // London saddle bag (use code KAY10 for 10% off only at Patricia Nash) // trench coat (similar)

Even if your most casual outfits are comprised of different elements, such as t-shirts or sweaters, joggers or cargo pants, you can still elevate your look with these simple tips. I’m all for being comfortable and casual, but I think it’s always a good idea to look a little pulled together and polished.

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Blessed for My Day

This we we’re walking through Psalm 19. See the previous two blog posts for my thoughts on verses 1-11. In verses 12 and 13, David, the author of this Psalm, seeks the Lord’s help in overcoming “the error of his ways.” This is definitely a prayer worth praying with him.

David desired to be holy before the Lord. Loved and protected by His God, David wanted to glorify Him through godly behavior. That’s the cry of my heart, too, and I’m sure it is your desire as well. But sometimes we are blind to our own faults. So David simply asked the Lord to help him spot his own errors, to clean up his hidden faults, to keep him from presumptuous sins (those that sneak in and become part of our character without detection) and to not let them become habits. Jesus taught His disciples a similar prayer when He told them to say, “and lead us not into temptation, but deliver us from evil…”

Who can discern his errors?
    Declare me innocent from hidden faults.
Keep back your servant also from presumptuous sins;
    let them not have dominion over me!
Then I shall be blameless,
    and innocent of great transgression. ~ Psalm 19:12-13

xoxo, Kay
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18 thoughts on “How to Elevate the Most Casual Outfits

  1. Casual outfits are indeed “where I live” almost every day, but I still want to look polished and put together. This post is very helpful on how to achieve that – thank you.

  2. First, I want to mention that you look great in this outfit you put together but for me it is too casual. I don’t wear sweatshirts that often, I bought one last Spring and ended up not wearing it and gave it as a Christmas gift. Not too much into tennis shoes either though they are trending now. Only wear for walking, exercising, or fishing, etc. Today I have on gray jeans with striped black and white tee shirt and casual black velour jacket. Loose fitting and casual and black mules. This is me casual and elevated, but as I said you look fabulous and works for you and I am sure some other ladies. Have a blessed day.

  3. I LOVE this simple formula. Thanks for reminding me of this. I have a darling pink sweatshirt that I will try this with. Your details are simple, but impactful. I forgot the cuffs were trending.

    I have not been getting your daily emails. I checked my junk box and they are not there. Should I resubscribe? I don’t know if I’m the only one?

    Have a delightful day!

    1. Hi Karin, I’m sorry to hear you’ve not been receiving the emails. According to my Mailchimp records your emails were sent and delivered to your email inbox. So if you’ve checked spam and didn’t find them there, you might want to unsubscribe and subscribe again. I don’t know what else to tell you.

  4. Just a quick caution when seeking new sweatshirts. If it is fleece lined, it will be WARM. I am in So Cal and it needs to be really cool for a fleece lined sweatshirt. I find they do not breathe as well, and I tend to feel sweaty. So, I always try to opt for the standard style or maybe even the french terry. I am so hopeful I can find one in that beautiful light blue you are wearing. I love that combo and, like you, wear light blue easily. On another note, how do you keep your shoes looking so fresh and new? You mention often that your shoes are a couple years old, but they look brand new. How do you do it???

    1. Hahaha! I really don’t know. I was wondering that myself as I typed in that they were a few years old now. But I really do wear them quite often. I guess I don’t wear these white leather sneakers in the mud or to dirty places really. But I definitely wear them frequently. No idea!

  5. I’m so happy to see you are human and wear casual clothes. You look great in that outfit! I am a creature of comfort and put on sweatshirt and athletic pants as soon as I get home from anywhere. I do wear my old house rags if I’m cooking to not ruin my nicer sweatshirts. I wear my nicer casual clothes to the park to walk sometimes, but always dress better for errands. There are people who wear their pretty clothes at home in the house but I just can’t…..nothing is as comfortable as sweats and tee shirts.

  6. I love a pretty sweatshirt and always elevate it like you suggested. Thanks for the roll up idea for jeans. I have those same ones. Win, win. Lots of sneakers ordered; will see what I choose. Blue is lovely on you

    1. LOL! I really have no idea why they stay so clean. I do indeed wear these particular sneakers a lot, and they are at least two years old if not more. I guess I don’t wear them places that are really dirty, like dirt parking lots or out hiking or anything like that. But I do wear them frequently, and I don’t do anything special to keep them clean.

    2. Hi, our lovely Kay is great! Her sneakers always look perfect! I don’t wear mine in dirt or mud either, but for the occasional spruce up, I’ve had good luck with the “magic erasers.” I just buy the Great Value brand & just break off a small piece. I hope this might help you!

  7. Jeans and a sweatshirt is pretty much a “stay at home” outfit for me. A little too casual for going out even with a new sweatshirt. I tend to wear jeans and a sweater or collared shirt with sweater/puffer vest or even a tee shirt with a blazer on top. I wear sweatshirts to hit the gym, play sports, or just hang at home when it’s cold and rainy

  8. Just my speed. I live in the country and a blazer is just too dressy for everyday. The blue sweatshirt looks so pretty on you, but dropped shoulders make my narrow shoulders look even more narrow.

  9. I was reading Psalm 19 last week. The NKJV says cleanse me from my secret faults. What you said is true. Many times we don’t know it but the Holy Spirit can show us. Blue is a good color on you. I started to wear my spring colored sweatshirts last week. We’ve been having spring weather for a couple of weeks now. Enjoyed this post.

  10. Thank you for these great tips for a casual jeans and sweatshirt outfit. I also work from home and my daily goal is to dress myself in an outfit that I would at least be comfortable going to the grocery store without changing my clothes into something “ better”. Lol, I know – lofty goals! I do put a bit of makeup and jewelry on each day and it makes a great impact with any outfit. I will definitely be trying the roll up on my jeans. That will bring back memories! It will be so helpful though when I find my full length straight jeans competing with my sneakers. Thank you for the reminder that it’s on trend again. Lastly, I just want to tell you how beautifully the cool based colors compliment you. I notice it every time you wear cool colors. You and the blue= stunning!

  11. I’m interpreting elevated in this case as putting in some effort into your look. You’re right that we can look good even if we’re casual.

  12. I loved your suggestion of turning a wide cuff on jeans. I recently bought a pair of classic straight Levi’s from Kohl’s that I saw on your post. This will be great for these and give them more life going into spring.
    Thanks for all that you do.

  13. Nice to see casual clothes! I would advise strongly against that drop shoulder in a heavy fabric though. It adds a lot of pounds!!!