5 Tips to Help You Look Great in Jeans Over 50

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.

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.

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.

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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.

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.

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.

• 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.

• 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.

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.

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.

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.

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.

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!

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.

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.

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.

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.

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.

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.

• 3 More Fall 2023 Trends to Try Right Now – Denim Skirts rule!
• Denim Trend to Wear Now & Later: Wide Leg Crop Jeans
• Denim Trend to Wear Now & Later: Wide Leg Full Length Jeans
• The Denim I Wore During Denim Week – My real life outfits of the week

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.