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How to Wear Relaxed Fit Straight Leg Jeans

February 2, 2023

If you, like me, love the casual aesthetic of the relaxed fit straight leg jeans that are currently trending, this post is for you! If I were in my twenties again (heaven help!) and about 20 pounds lighter, I would so wear the truly relaxed fit, generous cut jeans we’re seeing these days. But since I’m inching ever so close to 60 (I’ll be 59 later this month!) and don’t have the super slender body of my twenties, I’ve opted instead for some slightly relaxed fit jeans with a straight leg silhouette. You absolutely can wear the “baggier” jeans if you’d like and I will think you are oh so cool. But today I’m simply sharing how to wear relaxed fit straight leg jeans stylishly over 50. Let’s do this!

How to Wear Relaxed Fit Straight Leg Jeans Stylishly Over 50

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Classic straight leg jeans are always in style. And the more fitted, slender, straight legs always look classy and flattering on most body shapes and proportions. I love my classic straight leg jeans from Talbots. I have them in a dark wash and a lighter wash, and they have similar ones in stock now. You can’t beat those classic straight leg jeans when you want to look a little more elevated and polished.

But, while those slimmer fit jeans are in style, the fuller legs of the relaxed fit straight leg jeans are even more modern and on trend. They’re inherently more casual looking, but you absolutely can elevate them with the right footwear, accessories and tops. So don’t assume they’re only for casual Saturdays.

Below I’m styling two pair of relaxed fit straight leg jeans. We’ll start with the darker wash of the two.

I love these AG Alexxis high waist straight leg jeans. My exact wash is no longer available, so I’ve linked you to a selection of these Alexxis high waist jeans at Nordstrom. I size up to a 31 in these jeans, but they fit very comfortably and even a little roomy. Remember, these are supposed to be a relaxed fit, so it’s okay if they don’t fit skin tight.

Alexxis Straight Leg Jeans
Alexxis high waist jeans // booties (no longer in brown) // shirt (more economical) // necklace // similar belt // sweater

There was a day when it was considered gauche if your jeans were more than 1/2 inch off the floor with your heels, but that’s no longer the case. So you really have a lot of wiggle room and can wear one pair of jeans with multiple heel heights. Still, your full length relaxed fit straight leg jeans will look most flattering if the hemline at least doesn’t sit above the top of the heel. I love this jean silhouette with a nice bootie. And it’s an easy look to wear since the leg width accommodates most any bootie shaft.

Another heel option for these relaxed fit straight leg jeans is a pump. I’m wearing my Ally block heel pumps with these jeans below.

Relaxed Fit Straight Leg Jeans with PUmps
Alexxis high waist jeans // shirt (more economical) // necklace // similar belt // sweater // pumps (use code KAYHEELS for $40 off first pair of heels at Ally)

Because relaxed fit jeans are generally fuller in the legs, it’s smart to at least give your top a front tuck if you’re wearing a similarly blousy shirt. That little bit of structure can really help with proportions. Remember, proportions are not just about lengths. You also want to create proportion with the fullness of your clothing. Generally we like to have fullness in just one area and create a more trim appearance in the other part. You can wear a trending oversize shirt, like the one I’m wearing (more economical), but to create those pleasing proportions add a tuck and a belt.

Adding the sweater around my shoulders is a little trick that helps bring the focus up toward my face and away from my waistline. Still don’t like the look of tucking your shirt? Then add a third piece like I did below.

Relaxed Fit Straight Leg Jeans with a Cardigan
Alexxis high waist jeans // denim shirt // necklace // similar belt // similar Chelsea boots // cardigan // earrings

Here I’ve added this pretty multicolored cardigan over my tucked denim snap front shirt. This is a great way to wear denim on denim, by the way – adding that third piece to “lighten things up” a little. But that slim fit, loose drape cardigan also creates a slenderizing effect over my tucked and belted shirt.

One of the biggest challenges of wearing relaxed fit jeans is to create a more slender silhouette up top, especially since a lot of us older ladies don’t care to wear extremely form fitting tops. So little tricks like this help a lot. Above I’m wearing my Chelsea boots, just so you can see another option. And below I’ve swapped out boots for a navy flat.

Relaxed Fit Straight Leg Jeans with Cardigan
Alexxis high waist jeans // denim shirt // necklace // similar belt // navy flat // cardigan // earrings

Flats like these are not my favorite choice with full length jeans, but if I’m going to wear them I prefer they have a pointy toe. I know ballet flats are really on trend, but somehow the look of a ballet flat with a full length jean has never been a favorite of mine. But that’s probably just my personal quirk. If you love that look, go for it. I’ll probably reserve my ballet flats for ankle length jeans and pants.

Next I switched to my Talbots high waist relaxed jeans. I’m so impressed that Talbots introduced these this month. I know a lot of Talbots shoppers may not like them, but I think they’re such a great nod to this jean trend. And the jeans are amazingly comfortable. That one customer review on the website? Yeah, that’s mine. Hahaha!

Here’s how I wore the jeans last Friday to see a movie with my husband.

How to Wear Relaxed Fit Straight Leg Jeans Stylishly Over 50 (1)
high waist relaxed jeans // hoodie // sneakers (size down 1 size at least) // earrings

The lighter wash, the intentional faded crease down the front and the slightly more relaxed fit definitely make these jeans more casual. But since they are also a nice lightweight denim, I think they’re going to be favorites all year long. These are the kind of jeans you enjoy changing into after a long day in dressier clothes. They just feel like home!

High Waist Relaxed Fit Jeans
high waist relaxed jeans // thermal pullover // sneakers (size down 1 size at least) // earrings // gold necklace // compass coin necklace

So wearing these straight leg relaxed fit jeans with a pretty red thermal pullover and sneakers (size down 1 size at least) is an obvious combination as we move into spring. The red thermal pullover is a nice lightweight waffle weave and I love the generous crew neck. Those sneakers are really fun and on trend, but definitely size down a full size. I did, and they’re still roomy. But I just tightened the laces and wore socks with them. Love! Comfortable right out of the box.

Wearing Relaxed Fit Straight Leg Jeans
high waist relaxed jeans // thermal pullover // sneakers (size down 1 size at least) // earrings // gold necklace // compass coin necklace // similar utility jacket

I just added my utility jacket above after giving my thermal pullover a gentle front tuck. Whenever I can tuck my tops, even if just a little, I do it. I love the proportions it gives me. My utility jacket is from the Nordstrom Anniversary Sale last summer and no longer available. I have this similar utility jacket from Talbots, but I’m returning it. I felt like it was a little thin and not as flattering. I hear really good things about this utility jacket from other influencers, and the price is great.

High Waist Relaxed Fit Jeans
high waist relaxed jeans // earrings // necklace // shirt (more economical) // similar sneakers (more economical) // cropped field jacket

I really like the look of a white shirt (more economical) with these lighter wash jeans. and the cropped field jacket nicely conceals my waistline while also adding interest. The only problem is that this cropped field jacket is quite large. I do like the jacket, but I need to return it for a small. So size down. It comes in two other colors. (By the way, the reason I know the cropped field jacket is too large is that it is very bulky in the back, with lots of excess fabric under the arms.)

a Blazer with Relaxed Fit Straight Leg Jeans
high waist relaxed jeans // earrings // necklace // shirt (more economical) // blazer and here // similar booties

Next I tried my relaxed fit blazer (and here) with the light wash jeans. The oversized blazers are definitely on trend, but I’m wondering if a more fitted blazer might work better with these relaxed jeans. It could just be the way I’m standing, too. But you’re definitely going to get a very relaxed, casual vibe if you combine these two relaxed fit pieces. Above I’m wearing booties for a cooler weather outfit and below I swapped them out for mules when it’s a little warmer.

a Blazer with Relaxed Fit Straight Leg Jeans
high waist relaxed jeans // earrings // necklace // shirt (more economical) // blazer and here // similar mules

Mules are probably not my favorite flat to pair with relaxed fit jeans, but they do work. My favorite flat to wear with these full length jeans is coming up!

Below I swapped in a fitted tank (similar) for the oversized button up shirt. I actually think that helps the look a little bit, but again I don’t like the way I’m standing. So take that for what you will. But I remember thinking the tank top definitely added some much needed definition.

a Blazer with Relaxed Fit Straight Leg Jeans
high waist relaxed jeans // earrings // gold necklace // compass coin necklace // loafers (similar) // tank (similar)

Above I swapped in loafers (similar), too, and I really like that shoe option. I think loafers are such a good choice for relaxed fit jeans. They add a little structure and polish while still looking casual and youthful. This is my favorite flat, other than sneakers, to wear with full length relaxed fit jeans.

Below I topped the high waist relaxed jeans and the tank (similar) with a new hot trend: the lady jacket. I’m actually planning a blog post about this trend, but they’re selling out so fast I’m struggling to get one that’s still in stock to share with you. This lady jacket is almost sold out, and the other one I recently purchased has sold out once and been restocked. This is one HOT trend! I’m seeing them everywhere.

Relaxed Fit Jeans with Lady Jacket
high waist relaxed jeans // earrings // tank (similar) // lady jacket (similar or here) // similar shoes (use code SARAHFLINTBA-KAYH for $50 off your first pair of Sarah Flint shoes)

Since the lady jacket (similar or here) is a more elevated third piece, I’ve worn shoes to match. Above I’m wearing a pair of feminine slingbacks that are no longer available from Sarah Flint. But you get the picture. Below I swapped in a lightweight ribbed turtleneck for now and early spring. And I changed my footwear to suede pumps so you can see these high waist relaxed jeans with heels.

Relaxed Fit Jeans with Lady Jacket
high waist relaxed jeans // earrings // ribbed turtleneck // pumps (use code KAYHEELS for $40 off your first pair of Ally heels) // lady jacket (similar or here)

So here are a few summarizing take-aways about wearing relaxed fit straight leg jeans:

  • Do your best to create a little structure somewhere in the outfit to balance out the loose, relaxed fit of the jeans.
  • Try to create proportionate fullness and slim fit by wearing a top that is close to the body when possible or desired.
  • If you wear a top that is also full, create better proportions by tucking, belting or adding a more structured completer piece.
  • Choose your footwear carefully. Simply try on different shoes to see what looks best to you, but keep in mind that some footwear will look more on point with this jean silhouette than others.
  • Accept that these jeans will look different on you than the more slender cuts. They’re supposed to! Have fun with them and enjoy the comfort.

I hope you’ve enjoyed today’s blog post. If you have questions I didn’t address, please share in the comments. I’m still learning about how to wear this trend myself. But I’m happy to share what I’ve learned along the way.

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Blessed for My Day

Honestly, I rarely turn on the news these days. I fear we are all struggling a bit with information overload as technology has evolved so much over recent decades. We have so much information thrown at us from a variety of sources every day, and it can be quite overwhelming. But when I do watch or read the news of the world I get another sense of overwhelm. I struggle with how to make heads or tails of it all. The issues all seem so polarizing and the voices on all the different sides are very loud and passionate.

This is why it is so important to seek the Lord as we strive to understand the world around us. We must come to terms with the fact that we, as Christians, will often (if not always) be at odds with the world around us, even more so as time goes on. Why is that? Because the person with the Holy Spirit within them has the potential to see things from God’s perspective, while the person without the Spirit considers God’s ways and the precepts from the Bible to be foolishness. So as we grapple with the news and patterns in our world, let’s allow the “mind of Christ” to guide us. And then let’s not be daunted when our views do not line up with prevailing thought.

The person without the Spirit does not accept the things that come from the Spirit of God but considers them foolishness, and cannot understand them because they are discerned only through the Spirit. The person with the Spirit makes judgments about all things, but such a person is not subject to merely human judgments, for,

“Who has known the mind of the Lord
    so as to instruct him?”

But we have the mind of Christ. ~ 1 Corinthians 2:14-16

xoxo, Kay
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20 thoughts on “How to Wear Relaxed Fit Straight Leg Jeans

  1. This was a very helpful post. I appreciate your summary at the end of the post with tips for best styling the relaxed straight leg jeans. And of course the photos of you styling the look helps immensely. You look absolutely beautiful. If you think of any more sources for the lady jackets please share with us. Talbots is all sold out of the one you modeled. Many thanks!

      1. I purchased two last year at Express. They are good quality and I really like them. One is pink, almost identical to yours, and one is a gray and white. I don’t know if they have something similar this year, but I would check.

  2. Not too sure about the relaxed fit on my frame. I am one size smaller on top. However, you have done a really nice job of showing how it can work. Thank you. I especially liked the lady jacket on you. The soft pink looked perfect with your whole vibe. It is YOU!

    1. I love all the looks on you, Kay. I agree the pink lady jacket is so cute especially with your lovely new hair style. Well done!
      Being 5’3″ and not as trim as you are (boo!), I have to play around with this a bit but I really like it a lot.
      As always, thanks for all the information.

  3. The Talbots jeans are so cute on you! The fit is perfect! May have to make a trip to my local store and try those on. I’m a bit unsure about the faded crease down the front – don’t usually like that look, but that’s just a personal taste thing. Thanks for this post – it’s so full of useful styling tips!

  4. Great outfit combinations Kay. My favorite is the light pink blazer which looks stunning on you with your hair and skin tone. Speaking of hair, your hair looks fabulous since you’ve had it layered a little more. You mentioned that you were going to eventually let your hair turn naturally gray. I ditched the hair dye almost a year ago, and had long dark hair. I had it cut short last summer. My hair currently is 95-98 percent naturally silver with quite a bit of white on top. I still have a little leftover dye on some ends. I’m very surprised at the color it turned out to be and I love it. I feel so free from having to color it. One less thing to deal with. If you have any questions about the transition process, please email me and I’ll explain in further detail.

  5. “Lady” jacket is adorable with jeans.Would love to see it also styled with work or church appropriate pants or skirt ( without looking too fussy).

  6. Fabulous post Kay! Thanks! I do have a pair of similar light-colored jeans and it was helpful to see these options. I would like to see the lighter jeans with a more structured gray blazer on you. I have one and am going to try it. What size is your red Evereve sweatshirt? It looks more pink on their website but your pics definitely read RED!

  7. I love all the looks on you, Kay. I agree the pink lady jacket is so cute especially with your lovely new hair style. Well done!
    Being 5’3″ and not as trim as you are (boo!), I have to play around with this a bit but I really like it a lot.
    As always, thanks for all the information.

  8. I loved this post!!! You looked great in each outfit and I love the looks you presented. Gave me son great possibilities.

  9. Thanks for the ideas with straight leg jeans. I do wear these and I think they are the most flattering and easy to style many ways. As far as your BFMD, I have not watched the main stream media for almost a year now. So much prejudice and false reporting. Have been watching Newsmax that I believe is a truthful reportint station and also conservative and Christian based. Give it a try sometime. God bless.

  10. Any thoughts on a petite frame and these style of jeans ? I love the look of your blazer with the white skirt and boots, have to say I agree with you on the ballet flats…not my choice as well. Thank you for this videos…loads of great info.

  11. Hi Kay! Great post with so many helpful tips. The outfits with the lady jacket are stunning, so classic and flattering. Love them! Thanks for all you do.

  12. Hi Kay, I’m 68, retired and have a question. I recently purchased weekender chino pants in chambray from Talbots outlet. They are so pretty but I don’t know how to style them! Help!

    1. Hi Gayle, a solid colored relaxed fit tee or a solid cotton sweater will be perfect for spring and into summer. You can also top them with a solid white button up shirt or a plaid. Finish off the outfit with sneakers or loafer for spring or sandals for summer.