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5 Tips to Help You Look Great in Jeans Over 50

August 12, 2023

We’re closing out Denim Week at Dressed for My Day with a special Saturday post. It’s been a fun week of focusing on all things denim so that when fall gets here we’ll be ready to rock our jeans and other denim garments with style. I thought I’d wrap it up with 5 tips to help us look great in jeans over 50.

5 tips to help you look great in jeans over 50

Thanks so much to City Beauty for sponsoring this bonus blog post. I choose my sponsors carefully and only work with brands that I love, that I use or wear and that potentially benefit you. I’d like to briefly share with you why I accepted City Beauty’s offer to sponsor this particular blog post.

City Beauty is a 100% Leaping Bunny and PETA-Certified Cruelty-Free company. They are based in California, and 81% of their workforce is powered by women. But most importantly to me, they are pro-aging. City Beauty products combine clean ingredients with research-backed science to deliver visible results designed to maintain skin health while helping it appear more youthful.

City Beauty
City Beauty – try their InvisiCrepe Body Balm and/or their Multi-Action Sculpting Cream for 50% off with code KAY50 just through 8/15/23

I use the City Beauty City Lash lash-enhancing serum every morning and evening along my lash line to effectively revitalize my lashes and get great results. I also use and love their Beyond Mascara because it applies nice and wet, and it doesn’t gloop on my lashes. And I’m a big fan of the City Beauty City Lips plumpers. You can always use my code KAY15 to get 15% off sitewide at City Beauty.

Body Balm
InvisiCrepe Body Balm is 50% off with code KAY50 through August 15, 2023

But this weekend through August 15, you can try the InvisiCrepe Body Balm and the Multi-Action Sculpting Cream, two products that are really making a difference for me, for 50% off with code KAY50. The InvisiCrepe Body Balm moisturizes skin at a deeper level and helps seal in hydration to fight the appearance of crepey skin. And the Multi-Action Sculpting Cream helps restore firmness and elasticity to skin that appears to be drooping or thinner.

City Beauty
Multi-Action Sculpting Cream is 50% off with code KAY50 through 8/15/23

Again, I’m so pleased to have a pro-aging brand sponsoring today’s post about how to look great in your jeans over 50. Great looking skin is certainly a step in the right direction!

How to Look Great in Your Jeans Over 50

I do what I can to look my very best, but I’m not really one for trying to look younger than I am. When we try to look younger we can end up looking disingenuous, a little clownish even. Instead, I think it’s smart – at any age – to aim for looking modern. When you add a few modern touches to your overall look, you actually end up looking more vibrant, more current and like your best self.

Wearing denim is one of those modern choices that can help a woman over 50 to look current and more youthful. Here are just a few tips to help us look great in our jeans over 50.

1. Wear jeans that fit nicely.

Good fit is always important. And as we get older we sometimes have to make a few adjustments in order to have jeans that fit nicely. Maybe you’ve lost weight and need to have your jeans taken in some. You can even have a tailor put darts in the rear of the jeans to prevent that saggy butt look.

jeans // sweater // shoes

Make sure your jeans fit you snug but not tight through the torso even if they are relaxed fit jeans. And in the front of your jeans you want them to generally lay flat across your body without puckering, pulling or bunching. That said, as you move about in your jeans sometimes those things are going to happen. But aim for a neat and tidy look across the front.

2. Wear your jeans at the right length.

These days anything goes when it comes to jean styles and silhouettes. Contemporary styles of jeans include straight, wide leg, flare, bootcut, demi-boot, slim, skinny, cargo and even lantern. So you can choose from any of those and look modern. However, if your jeans are the wrong length for that particular silhouette, it can wreck your look.

Jacket and Heels
wide leg, full length jeans // similar tee // similar blazer (more economical) // satchel // sandals // necklace

Really there are just two lengths (three if you want to puddle!) for modern denim: full length or ankle, sometimes called cropped.

  • Full length straight leg should rest slightly on the top of your shoe, draping down over your foot a little in the back and on the side.
  • Full length skinny jeans should end at the bend between your leg and foot.
Sneakers and Jeans and Blazer
wide leg, full length jeans // effortless jersey stripe square neck top (size down; wearing a Small) // necklace // houndstooth blazer (size down; wearing an 8) // belt (wearing m-l) // convertible shoulder bag // similar sneakers (GREAT more economical option)
  • Full length wide leg, bootcut or flare jeans should also rest on the top of your shoe with one gentle “break” in the fabric. See my right leg (on your left) in the photo above for what that gentle break looks like. Your jean leg should fall gently over the back and side of your shoe. Unless you’re going for the puddle effect – and I doubt any of my readers are – you’ll want your jeans to be about 1/2″ to 1″ from the floor with your shoes on.
Sarah Flint Pumps
Sarah Flint Emmas in espresso suede – new customers can use code SARAHFLINT-CCLAURAKAY1 for 15% off a full price order
  • Ankle or crop length jeans of any kind should hit right at the ankle bone or just above it. In fact, I think it’s safe to say they could be up to 1″ above your ankle bone, but no more than that.
Camp Shirt

Remember, ankle length jeans continue to be very on trend, very modern. And when we say “cropped length” these days, we’re really talking ankle length. Showing a little ankle can actually be very flattering and can even elongate the legs visually if you wear the right shoes and the best rise for you, tucking your top or wearing a cropped length top for optimal results.

Perfect Vintage Wide Leg Crop Jeans
Perfect Vintage Wide Leg Crop Jeans // similar tank // button up shirt // sandals // earrings no longer available (option) // chain link necklace // coin necklace // crossbody

One of the benefits of ankle jeans, in fact, is that you can get your jeans hemmed or cut to a raw edge at just the right length and then wear them with most any shoes, maintaining the right length. But full length jeans are a little trickier and need to be worn consistently with the same height heel or within about a 1″ margin.

jeans // shoes

That’s why I say I’m still a little torn over whether or not to cut off the jeans shown above to a true ankle length. They’re supposed to be ankle length jeans, but they run long on me. And they’re really kind of at that ambiguous length somewhere between full length and ankle. I’m still mulling this one over. So don’t be surprised if they show up a little shorter later. Ha!

3. Wear your jeans with modern shoes.

Just wearing jeans is not enough to look modern. We need to complete the outfit with other contemporary styling choices. Wearing modern shoes is one of the best ways to really look current and fresh. And they’ll help you look great in jeans over 50.

Wear your Colored Shoes with Confidence
sweater // Mother the Tripper button-fly jeans (comparable substitute / more economical option) // Kristina pointed toe mules (sized down 1/2 size) // Hudson medium convertible crossbody in earthenware // earrings // simple necklace // coin necklace // sunglasses (similar option)

Of course your options are myriad. But slides, mules and loafers will definitely look on trend this fall. Kitten heels and slingbacks are going to be popular, too. Later you can wear booties, especially some with a western vibe. And sneakers will always give your jeans outfit a modern twist.

These jeans are generally going to look best with a close fitting top to keep the outfit proportionate. Which proportions am I referring to? In your outfit it is best to have some of your outfit fitted and some of it more relaxed, especially if one of the pieces is very voluminous. So to balance the volume in the jeans, wear a more fitted top.
wide leg, full length jeans // effortless jersey stripe square neck top (size down; wearing a Small) // necklace // belt (wearing m-l) // convertible shoulder bag // similar sneakers (GREAT more economical option)

White leather sneakers – especially platform sneakers – are usually a great choice. But I always get compliments when I wear my retro trainers with my jeans outfits. And guess who it is that is complimenting me the most on those outfits? Young women in their 20s and 30s!

with retro trainers
Perfect Vintage Wide Leg Crop Jeans // similar tank // button up shirt // retro sneakers (similar option and another) // earrings no longer available (option) // chain link necklace // coin necklace // crossbody

4. Wear the right undies.

Nothing wrecks your jeans outfit like panty lines. Fortunately most jeans are pretty forgiving, but it’s still smart to consider your undergarment choices carefully. I have good luck with my Soma Vanishing Edge panties. They have every silhouette and style of panty imaginable, as well as different fabrications to choose from. So you do you. But I wear these with very good results. They don’t ride up and they don’t present lines beneath my clothing. You may prefer a thong or another full coverage panty. Just make sure they’re getting the job done!

5. Pair your tops and jeans strategically.

When you’re pairing tops and jeans there are several key considerations. First I like to think about intensity of color. Light wash jeans are very “in” right now. When I wear a light wash jeans I like to wear a light colored top to keep the contrast in intensity low.

linen button up shirt (sized down to small) // jeans (wearing size 31) // sandals // purse // coin necklace // other necklace // earrings // bracelet // watch (use code KAYHRMS for 15% off)

And when I wear dark wash jeans I like to wear a darker top for the same reason. But if you have high contrast in intensity in your physical features (eyes, skin and hair) you may prefer to have high contrast in intensity in your outfits. Thus you would wear a brighter or darker top with your light wash jeans and a lighter or softer toned top with your dark wash jeans. Make sense?

You might want to check out this video for more information about contrast in intensity.

But another consideration when choosing the top to wear with your jeans is proportions. And that works two ways.

One, you’ll want to create pleasing proportions in volume. Do this by wearing a slimmer fitting top with voluminous jeans or a fuller top with slimmer jeans.

Close Fitting Top with Wide Leg Full Length Jeans
wide leg, full length jeans // effortless jersey stripe square neck top (size down; wearing a Small) // necklace // belt (wearing m-l) // convertible shoulder bag // similar sneakers (GREAT more economical option)

And second you’ll want to consider the proportions of the lengths in your outfit. Ideally, you want to use your clothing to create 1/3 to 2/3 proportions with your body. In other words, with a jeans outfit, your top portion – from your collar to end of top – should be 1/3 of your look and your jeans to shoes should be 2/3 of your look. That’s what artists call the golden ration of design.

Wear Later
wide leg crop jeans // camp shirt // blazer old – not available (similar option and in plus sizes) // block heel pumps (more economical option) // necklace // earrings not available – similar option // crossbody // bangle

That may mean that you need to either tuck your top in – at least in the front – or you need to wear a more cropped length top. This is especially true if you are wearing ankle length jeans. If you’re wearing fuller length jeans you have a little more wiggle room with the length of your top. But your legs will look longer if you do keep your top shorter or tucked. In the photo above it also helped for me to wear darker pumps that helped continue the line of the jeans even though a little ankle shows.

curvy fit wide leg full length jeans
vest // jeans // similar tee // sneakers (more economical) // necklace

And if you’re concerned that tucking your top to create those pleasing proportions will expose an unflattering waistline, just add a third piece over your top. As long as it is worn open, your jacket, cardigan or other topper can be longer.

brown suede clutch (similar, same brand)
wide leg crop jeans // camp shirt // blazer old – not available (similar option and in plus sizes) // block heel pumps (more economical option) // necklace // earrings not available – similar option // crossbody // bangle

I hope you’re ready to rock your jeans. You absolutely can look great in jeans over 50. We just need to be smart about how we wear them. If you haven’t checked out the other posts in Denim Week be sure to do that. I’ve linked them below for you.

And this week we have two videos, both on the topic of denim. Wednesday I shared the Denim Trends for Fall 2023.

And in a special bonus video this weekend I shared How to Find the Perfect Jeans for You.

Don’t forget to check out City Beauty, especially their InvisiCrepe Body Balm and/or their Multi-Action Sculpting Cream for 50% off with code KAY50 just through 8/15/23.

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Blessed for My Day

People are hard to please. That’s why it’s so important for us to prioritize pleasing the Lord. If we aim to please Him, we will undoubtedly please some people, but others may be disappointed. But we mustn’t be too discouraged when this happens. It certainly happened to Christ. One minute the people were speaking well of Him and marveling at the “gracious words he was speaking.”

But just minutes later they became enraged over the truths He was speaking. Then even sought to kill Him for His words. This happened over and over in Jesus’ brief ministry, undoubtedly. And in the passage below He teaches us how to deal with such situations. He “went on His way.” That may seem ruthless and uncaring, but let’s remember that Jesus indeed prioritized pleasing the Father. Today if others do not understand the things you are doing but you are sure you are following the Lord’s direction? Go on your way. Seek to please the Father.

And all the people in the synagogue were filled with rage as they heard these things; and they got up and drove Him out of the city, and brought Him to the crest of the hill on which their city had been built, so that they could throw Him down from the cliff. But He passed through their midst and went on His way. ~ Luke 4:28-30

xoxo, Kay
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13 thoughts on “5 Tips to Help You Look Great in Jeans Over 50

  1. Love your denim week content! Just tried to order City Beauty products and the KAY50 code didn’t work (Sat, 9:22am) Wanted you to know!

    1. Hi Sue. Thanks so much for letting me know. I’ve contacted City Beauty and am waiting on a reply. They’re in California so it may be a few hours, but I’m sure they’ll get it fixed today.

  2. Wow! What a great post! So much info, thank you Kay for all you do. You truly are an inspiration to me and I look forward to your post daily. Hope you have a wonderful rest of your week and put your feet up or get out and do something fun!

  3. Just want you to know that the KAY50 promo is not working. Just tried it from your links and in City Beauty another way. No 50% off on those two skin items. Today is 8/11/23.

    1. Hi Kelly. It’s working now. I think they must have set it to the wrong time originally. But I just tried it and it worked for me.

  4. Kay, just thought it might be of interest to you that I got a link from TJMaxx today featuring DENIM clothing! You are so right on about your predictions!

    Love your daily posts and videos and appreciate so much all the work that goes into achieving this! Thank you. Nikii

  5. Very informative post. As a short woman with short legs I follow your advice. I love the wide leg jeans with the blazers on you. I totally have embraced this style. When they go out of style I will wear straight legs never skinny especially the really tight ones. I’m going to check out the lash serum. I have to know what the ingredients are because I am allergic to most of them if they contain a certain chemical.

  6. I always look forward to your posts and especially the videos. I can see how hard you work because one week of Dressed for My Day is the equivalent of an entire magazine of information. The video on contrast and intensity is amazing. The examples were so helpful, as I can now distinguish both aspects of color and how to wear them. I have always worn dark jeans because I felt they were dressier. I have low intensity features and you now taught me how to wear lighter bottom colors to my advantage. Thanks for all the hard work, Kay. You are the best in what you do, and congratulations on your 100,000 subscribers!

  7. Kay, I have enjoyed your “denim week” so much!
    Plllleeeeez publish your London wardrobe ASAP! We leave Weds for London and I am struggling with finalizing a good mix and match travel capsule!
    I would so appreciate knowing what YOU are taking!
    TYIA!!!!! Sharon

    1. Oh wow! Well, have an amazing time. I’m sorry that I won’t be able to get that post up before then. But I can tell you that I’m basically taking four different pairs of black pants and then tops that go with all of them. Well, duh, of course they do if they’are all black. Hahaha! I’m wearing my black Talbots travel pants and taking my black cotton ankle pants , some antique black jeans and these Eileen Fisher pants I got in the NSale . Tops include this button up shirt in blue, this t-shirt This is my crossbody in black and I’m taking these sandals in oily shadow nubuck. I got this scarf in the NSale and it sold out, but it’s back! It’s a map of East London; how cool is that! I’m wearing these sneakers on the plane with those travel pants and that heart striped tee. And I’m taking a couple of solid white tees and tanks and this fun shirt to wear over them. I decided not to take a dress, but I think that would certainly be nice. Hope that helps a little. Oh, and I did throw a few colored tops in, too, including this vest and this vest

  8. How exciting about your trip to London. My son and I plan to go next year. Please don’t hesitate to send me all the details of packing, what you can and cannot pack for the season and where you go, etc. I’m excited because you’re going. Love all the outfits you put together in this post. It’s seems so effortless when you put them together but when I do it’s scary. I’m older than you so it takes a lot of deciding for me. I change clothes too many times. I’m not satisfied as to how I look. I’m only 4’11” and weight 130 lbs. Yes I have the love handles. Anyway hope you have a great week and try not to stress packing. I’m sure you have it down to a science.

  9. Loved your Denim Style . I like how you explained about 1/3 and 2/3 thirds Ratio it makes loads of sense to me now and also the low and high contrast , Im a low contrast so i’ve tried out your advice with my wardrobe and you’re so right it works better. Kay loved all your denim outfits may I say you totally rock that Stripe Breton Top and Wide Leg Jeans with your Sneakers and I love your check jacket you wore with them , very clever how that subtle check goes with the stripe I never would have thought it ! Very fresh and modern . And I love your Wide Leg Jeans worn with the Vest and Tee . I think you are right about maybe cutting those other jeans to your ankle length , believe me it will plague you till you do 😂. Thank you for all your advice and inspiration ❤️