It's so nice to meet you!
Get to know Kay...

2 Ways to Wear Wide-Leg Casual Pants

October 16, 2023

I’m a firm believer in avoiding the trap of trying to look younger as a woman over 50, but, instead, aiming to look modern. I think that when we aim for modern, we actually do look fresher, more vibrant and even more youthful. One of the ways we can look a little more contemporary is to wear current silhouettes of trousers and jeans. So today I’m sharing two ways to wear the trending wide-leg casual pants this fall.

2 ways to wear Wide Leg Casual Pants

This post contains affiliate links. When you shop through my links I potentially earn a commission on your purchases, but at no additional cost to you. Thank you so much for supporting my work here by shopping my links.

Before we move on to my illustrations and tips, let’s agree that not everyone will opt to wear the wide-leg casual pants. Some women will not care for the style and others will conclude that they’re not best for their personal style aesthetic, shape, height or proportions. That’s to be expected. But for those of us who do desire to try them (because they’re extremely comfortable, fun and current!), I believe we absolutely should be able to wear them with confidence and joy. Here’s how to make them work for you.

#1 – Find a pair of wide-leg casual pants you love and that feel comfortable and authentic to you.

2 ways to wear Wide Leg Casual Pants

I immediately fell in love with these Harlow wide-leg pants from Madewell. The 48% TENCEL™ lyocell, 33% cotton and 19% linen blend pants have the softest hand and such a lovely drape. They’re a nice weight for fall and into winter (in most climates), and they feel sporty and classic.

I’m wearing the Harlow wide-leg pants in the lower of my two usual sizes, a size regular 8. These are in the color seed khaki. But the Harlow wide-leg pants come in petite, tall and plus sizes and, at least in the regular fit, nine great shades. I’m ordering the chocolate raisin today, but I also love the true black and the acorn. Really, so many great colors to choose from. And yes, these full-length wide-leg casual pants are indeed machine washable. (I will undoubtedly hang mine to dry on a drying rack.)

48% TENCEL™ lyocell/33% cotton/19% linen
Harlow wide-leg pants in seed khaki (wearing size regular 8)

#2 – Purchase wide-leg casual pants that fit snug in the waist, looser in the hips and legs.

My second tip is to make sure you get wide-leg casual pants that fit you correctly. Originally I tried these in size 10 and I thought they worked fine. But when I went down to my lower size, a size 8 here, I noticed a huge difference. Unless you’re as thin and svelte as the models shown wearing them loose on their hips, I suggest buying wide-leg casual pants that fit snug in the waist, looser in the hips and legs.

wide-leg pants

By the way, let’s address the pleats in the pants. At first I recommended we ladies over 50 stay away from pleated pants. But in the last couple of years I’ve seen so many pleated pants that are created beautifully, so I’ve changed my tune there. Look for pleats that create a little fullness, but still lay flat. And do what works best for your body shape, too.

#3 – Wear a base layer top that fits close to your body.

You don’t have to wear a tight top or a body suit…unless you want to. But I do find that these wide-leg casual pants look better on most of us if we wear a top that fits close to the body. I’m wearing a favorite tank in both of the outfits I’m sharing today. It’s no longer available (this one is similar), but you get the vibe. Depending on the temperature outside, you could opt for a slim-fitting turtleneck, a close-fitting ribbed tee or a similar tank.

wide-leg casual pants
lightweight button-up shirt (more economical option) // similar tank // wide-leg casual pants (run a little large) // earrings // necklace // bracelet // similar sneakers (more economical option)

#4 – Use a second layer and style hacks to create a more flattering waistline.

I have an hourglass shape, but I still have a larger waistline than I once did. And even if you have an apple or oval shape, you will probably be able to achieve a silhouette you like if you’ll use a second layer to work a little magic around your waistline. In the outfit above I wore a lightweight button-up shirt over my tank and tied it at the waist, helping to create a little balance and some definition around my middle.

denim button-up shirt // similar tank // wide-leg casual pants (run a little large) // earrings // necklace // similar sneakers (more economical option) // belt // bucket bag

And in this second outfit I wore a denim button-up shirt open over the same combination. Switching out this one component and styling it a little differently created a completely new look, but equally flattering. The key is that fitted top underneath.

2 Ways to Wear Wide-Leg Casual Pants for Fall
denim button-up shirt // similar tank // wide-leg casual pants (run a little large) // earrings // necklace // similar sneakers (more economical option) // belt // bucket bag

Wearing the denim button-up shirt buttoned and without the tank would look unshapely unless I tucked it in. But when you wear the denim button-up shirt as a sort of cardigan or completer piece over the fitted top, it gives the illusion of an even shapelier waistline. Of course one more key really helps…

#5 – Wear a belt if at all possible with your body shape and proportions.

denim button-up shirt

Especially when worn under a completer piece like I’ve done here, a belt can help add definition and create pleasing proportions. It’s also just a great accessory that helps elevate an outfit and tie the look together.

#6 – Wear the right footwear to complete your look.

denim button-up shirt

While you will see models and other svelte and younger women wear their wide-leg casual pants puddling on the ground, these trousers will look best on most of us worn just about a half inch to one and a half inches off the ground. Ideally they should hit the top of your shoes and have one bend or crease just above your foot as mine do above. I like wide-leg casual pants worn with booties, mules, loafers and sneakers for a casual look. For a more office-appropriate outfit you might opt for pumps or other heels.

#7 – Accessorize your outfit to look pulled together, not sloppy.

Wide-leg casual pants can feel and look a little sloppy unless we take the time to pull the outfit together a little. Use a style hack like rolling your sleeves, tucking your top, flipping up your collar or adding a belt to add a little interest and intentionality to the look.


Then accessorize your outfit with jewelry and coordinating shoes, handbag and/or belt. I pulled this second look together with a coordinating belt and bucket bag.

denim button-up shirt // similar tank // wide-leg casual pants (run a little large) // earrings // necklace // similar sneakers (more economical option) // belt // bucket bag

I truly love these particular wide-leg casual pants and actually wore them to church yesterday. I’ll share that outfit in my LTK shop and in Friday’s blog post. But I’ll also style these wide-leg casual pants two more ways – a tad more elevated – in a blog post later in the week.

2 ways to wear Wide Leg Casual Pants

Thanks so much for dropping in. I hope these tips help you to feel confident and stylish in wide-leg casual pants if you choose to wear them. And if this pants silhouette is not for you, hold tight. I’ve got lots more style inspiration with different silhouettes coming your way this week.

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

Don’t Miss a Post:

If you like what you’re seeing here at Dressed for My Day, I invite you to subscribe to my email list. You can receive an email each time I post (about 6 times weekly) or just on Saturdays. You choose! But you’ll also receive the password to open up all the subscriber freebies I offer.

Would you like to subscribe to Dressed for My Day?

Spread the love

Blessed for My Day

What has God done in your life recently that you could not have done for yourself? How has He moved in your world? How have you heard Him speak to you? Sometimes we need to pause and just praise the good Lord for all He is doing in our lives.

Truly, there is no one like the Lord God in my life. He has been faithful and good and merciful and kind. He has worked all things together for good in my life, especially as I love back in the rearview mirror and trace His fingerprints on the days I have lived. And I will trust the Lord with the days ahead, too. He is good and worthy to be praised.

For this reason You are great, Lord God; for there is no one like You, and there is no God except You, according to all that we have heard with our ears. ~ 2 Samuel 7:22

xoxo, Kay
Join the Conversation

This site uses Akismet to reduce spam. Learn how your comment data is processed.

20 thoughts on “2 Ways to Wear Wide-Leg Casual Pants

  1. Love these 2 styling ideas ♥️♥️♥️♥️You look so good Kay. The wide leg pant is my favourite Silhouette , as is a Bootleg , But I said in one of your Blogs last week about trying a new jean silhouette , that I would give the ‘Straight Leg’ a Go (after not wearing it for 35 years) Well I have styled those Straight Leg Jeans my friend gifted me for 4 days now and I Love them ♥️i’ve had compliments off of my husband and friends and they will stay in my wardrobe now , so Thank you Xx

    Loved your Devotional today and ‘God is Good’ .

  2. I didn’t think I would ever wear pleated pants again, but I tried these on in black, loved them, and bought them. I think the drapey fabric is part of what makes them look so good on. I wore mine to church last weekend and am looking forward to wearing them more casually soon! They look great on you, Kay, and both outfits are so cute! Thanks for another great blog post. 😊

  3. Really nice BFMD. I still do not like wide leg pants on me. Have tried many times, but I am short and I think they make me look shorter and dumpy. I think I will skip this trend all together. If they are just a little flair I think they work all right for me, will see. By the time I decide to make the jump, they will probably be out of style. lol. Glad you had a nice baby shower for Abigail.

  4. I love those pants! My favorite is the one with the white shirt-I just like that silhouette better. I’m considering the chocolate raisin. I don’t have much brown in my wardrobe and it is a good color for me.

    God is good! I love him so much!

    You sometimes ask us what things we would be interested in. The fairtrade movement is growing. My daughter is telling me about it. There is an app called “Good on you” which rates companies. I would be interested in clothes from fairtrade companies who aren’t using slave or child labor. I am TRYING to move in that direction, but it is hard because I don’t know how good the quality is or what brands are geared for my age, or which ones have good style…. I would be interested in a post about this, I don’t know if others would be-I’m probably not the only one with adult children who are into this:)

    1. Thanks for sharing, Karin. I’ve done posts on Slow Fashion, but not specifically fairtrade. I’ll definitely look into that. But you can rest assured that I really try to only support brands and retailers that are at least conscientiously moving in that direction. I’ll work on it!

  5. I love the drape of these pants on you. I have been nervous to wear wide leg pants. These two ways to style wide leg pants was so helpful for me. I appreciate the perspective from our age range. As the models don’t look anything like me. My favorite is first outfit on you and it makes me wonder if I too could pull of wide leg pants. Thanks for encouragement

  6. I have to say that the white shirt looks just tickled my fancy Kay. You look so modern and fresh!!

  7. This post is both helpful and timely, Kay! I just bought a pair of wide-leg pants, and I am struggling with how to style them. Your tips confirmed some of my thoughts – now I just need to pick up a couple of slim-fitting tops. I look forward to the post on more elevated looks – my pants are not as casual as these (gorgeous) pants, and I need some more elevated ideas. Thank you so much for all you do! I especially enjoy the Blessed For My Day.

  8. Hi Kay. I love these wide leg pants and you styled them beautifully! I just now purchased them in chocolate raisin. If I love them as much as I hope to, I will purchase in another color also. Do you think you might be able to suggest the color of tops you can wear with this chocolate raisin shade? Thank you!

    1. Hi Anne, I think the chocolate raisin will probably look great with some neutrals like white, beige and even black. But I anticipate trying them with the trending deep red and lavender, too. I haven’t actually seen them in person, so I don’t know for sure. But I bet they’ll work nicely with some shades of turquoise and blue, too.

  9. i love these pants! I like wide-leg pants in general and these look really great on you. Thanks for all you do! I love your posts and your devotionals.

  10. I love wide leg pants and jeans! I have a triangle shape and they work. It’s very hard to find clothes to fit a 27 inch waist with 40.5 inch hips so this silhouette works for me! My favorite part is always Blessed For My Day. Lately I have been thanking the Lord for my house. I spent so many years without a house of my own and there is absolutely no way with the current economy that I could possibly afford a home. My home is older and needs work but it’s paid for. Yes, I am so thankful for Jesus’ sacrifice and that I have a home in heaven, but my earthly home means so much to me. I’m so thankful.

  11. My favorite way to wear wide leg pants is with a closer fitting top. Wearing a closer fitting jean jacket and top is my favorite casual way to wear wide leg pants. At 5’4 and a V shape this helps to add balance.

  12. Sorry, Kay, I’m one of those people who hate the wide-legged pants. I just think they look messy.Since I’m short, I know I’ d have to get them altered so that they wouldn’t trail on the ground.

  13. These pants look great on you, Kaye. I appreciate that you share different ways to wear the newer styles. Styles that I might not give a second thought to wearing. Have a blessed day.

  14. I like your style tips and these pants look great on you. That being said, I struggle with all these pant silhouettes that seem to change every year. Being on a fixed income, I cannot afford to keep changing out my pants nor do I have room to store them. I stick to straight leg pants and that seems to work for me. Men don’t have to deal with nearly as often as we do!

    1. Hi Jennifer. I hear ya. Don’t feel like you need to keep up. Find a silhouette that works well for you and stick with it. You’ll rarely go wrong with classic straight leg trousers and jeans. And a bootcut is a classic too.