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Early Fall Outfit – Wide Leg Cropped Jeans

August 8, 2023

It’s denim week here at Dressed for My Day, so I’m trying to provide as much information as I possibly can concerning jeans and their denim counterparts. I’ll really get to the nitty-gritty of what’s in style for fall 2023 and the task of selecting jeans perfect for you in this week’s videos (yes, there are two!). But today I’m providing a little style inspiration with one of my favorite pairs of straight, wide-leg ankle jeans, and they’re also at an affordable price.

Denim Trend to Wear Now and Later

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Today I’m sharing a pair of Madewell’s perfect vintage wide leg crop jeans, and they are simply a little wide in the legs. Madewell does a great job with jeans. They tend to be a little heavier than some of the premium brands I like, but I still love their jeans. They also usually have less elasticity and a higher percentage of cotton. But these 99%, 1% elastane jeans do have a decent little amount of stretch in them.

Wear Now

Madewell’s perfect vintage jeans are known for sucking you in nicely in your torso, and these definitely do that. I size down at Madewell, and here I’m wearing a 29 in their perfect vintage wide leg crop jeans.

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

But as much as I love these jeans for now and later, let’s focus a little more on the styling. I want us to be able to style similar silhouettes and lengths for now and later because I think these make a great transition jean from summer to early fall. And later I absolutely can wear them with booties, but that’s for another day, another blog post.

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

For now I can wear my wide leg crop jeans with a tank and lightweight shirt. You absolutely can continue to wear your linen button up shirts into fall, but I’ll probably start leaning into other lightweight fabrics soon. I personally like to reserve my linen for summer. But this Cloth & Stone windowpane button down shirt is perfect for now and later. It runs true to size.

Summer Outfit

These are high waist wide leg crop jeans so I could wear a cropped length top with them and leave it untucked. But for best proportions with cropped length jeans, I do suggest trying a tuck or front tuck. That way you’re legs will look longer and you’ll have those desirable 1/3 to 2/3 proportions.

Above I wore the wide leg crop jeans with strappy sandals. Those also help to visually elongate the legs. But don’t be afraid to try other shoes options with your wide leg cropped length jeans, too. Below I swapped in my neutral colored retro trainers (another cool option). They may not be everyone’s cup of tea, but they’re very on trend and this combination is definitely a modern option.

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

I’ll be honest, I get compliments on my outfits quite frequently when I’m out and about. But the item I’m wearing almost every time that I’m complimented by a younger woman is a pair of retro trainers. I kid you not. And the compliments come when I’m wearing them styled in outfits like this one. In fact, two different young women paused on the street to compliment me during this very photo shoot. Just saying. So don’t knock this look until you’ve tried it!

But, for you traditionalists, let’s move on to another look I styled with these Madewell wide leg crop jeans. This one is for a little later as we start edging our way into fall.

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

I love elevating a pair of jeans with a pretty blouse and a great blazer. Throw on a pair of classy pumps to seal the deal! This is an outfit I would gladly wear to lunch with friends or a casual meeting. And it’s perfect for a casual work environment, too. And yes, I’d definitely wear this classy combo to our casual church service.

Camp Shirt and Blazer

I’m wearing this pretty silky camp shirt in dark roast brown, but it comes in several other nice colors, too. My blazer is from a couple of winters ago, so it’s not available. But this one from Madewell is quite similar with its oversize silhouette. It comes in plus sizes, too. Again, the secret to this outfit is giving that shirt a gentle front tuck. And yes, I can wear it alone. So if it’s too hot for the blazer, this brown camp shirt still holds its own with my wide leg crop jeans.

Camp Shirt

I completed the look with my newest pumps from Sarah Flint. I earned these Emmas in Espresso suede, and they’re pricey. But I have to say, they are stunning and extremely comfortable. NEW Sarah Flint customers can use code SARAHFLINT-CCLAURAKAY1 to get 15% off a full price order.

Sarah Flint Pumps
Sarah Flint Emmas in espresso suede – new customers can use code SARAHFLINT-CCLAURAKAY1 for 15% off a full price order

But you can certainly create a similar look with pumps or pointy toe flats from your closet. I showed my Kate Spade Hudson convertible crossbody with the look some, but for a more on trend look I added a brown suede clutch (similar, same brand). Have I mentioned that clutches are really trending for 2023?

Clutches are Trending
brown suede clutch (similar, same brand)

So to summarize, wide leg crop jeans can be so versatile and fun to style both now and later this fall. You can wear so many different shoe choices with them. You can dress them down or up. And you can create better proportions by giving your top a gentle front tuck.

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 // brown suede clutch (similar, same brand) // bracelet

Stay tuned for more Denim Week posts! But tomorrow join me on my YouTube Channel for What’s Trending in Denim for 2023. And if you’ve not already subscribed to my YouTube channel, be sure to do that. I’ll wrap up Denim Week on Saturday with a bonus video on How to Find Your Perfect Jeans.

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Blessed for My Day

I’m a huge fan of Romans 8:28. But, because I’m also a stickler for keeping scriptures in context, I don’t even allow myself to think on this popular verse without also recalling the next two key verses. You see, God does indeed work all things together for our good. And I love that. I’m glad that I can know with certainty that even the worst things in my life will contribute to something positive in the end. 

But it’s important to remember what Paul meant by “good” in verse 28. Good, as it is used here, doesn’t necessarily mean sweet, easy or comfortable. The following two verses remind me that God’s priority for me is to shape me into Christ-likeness. He’s more concerned about character than my comfort. So yes, God is working all things together for my good, but that means He is using the pain, the conflicts, the detours, the delays and the dilemmas to conform me to the image or likeness of Jesus. And that is indeed a GOOD thing.

And we know that in all things God works for the good of those who love him, who have been called according to his purpose. For those God foreknew he also predestined to be conformed to the image of his Son, that he might be the firstborn among many brothers and sisters. And those he predestined, he also called; those he called, he also justified; those he justified, he also glorified. ~ Romans 8:28-30

xoxo, Kay
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16 thoughts on “Early Fall Outfit – Wide Leg Cropped Jeans

  1. Good afternoon, Kay,
    I don’t want to disturb your well deserved rest but want to thank you for the extra effort in posting your blog today. You and James deserve a GOLD STAR today. Can you tell I’m a retired teacher who continues to enjoy giving GOLD STARS when so deserved!

  2. Kay,

    I would have skipped the post today after what you went through, but I’m glad you didn’t as I always look forward to your emails.

    The wide leg cropped jeans are my favorites. I have 2 pair from Talbots and I’m wearing one of them today. I think they’re so comfortable. I hope you show us more ways to style these.

    Take care.

  3. So sorry to be hear about your plumbing issues but so glad Everything is fixed now. Like your outfits. I know you say you get Compliments about your trainers with your jean outfits, and they are comfortable and all But I have never been much of a tennis shoe person except for when I go for walks or sports etcetera. I do like the other shoes you are wearing. Nice blazer.

    1. Hahaha, that’s why I share multiple shoe options when I can. James actually snapped a photo of me today as I was sitting down on the sidewalk changing shoes. I guess I should have him save it. He was just being funny. But it’s what I do!

  4. Ugh! Plumbing issues stink! No pun intended. We had a water pipe burst in the wall and ceiling of our newly finished basement last year all over new flooring and new drywall.😫
    You deserve a rest! Thanks for rallying and posting today, always look forward to it.

    1. Yes, my parents were out of their living space for about three months due to a leak in their walls. It was no small ordeal. Fortunately we have no damage. And we’ve been enjoying a restful evening.

  5. OH MY GOODNESS! You and your husband deserve a medal for dedication. You both soooo deserve a rest. To tell you the truth, I was a little worried about you bc you are so dependable, and your posts appear like clock work. I said a quick prayer that nothing major went wrong. When I saw your post come in, I was happy bc I knew you were OK. On the other hand, when I read it, I was not happy that you continued on in spite of your stressful day. Bottom line, glad you are fine, and that your home survived! BTW, Loved your post…I’m a big fan of Madewell jeans! Now rest up!

    1. Hahaha! Probably if I hadn’t made a big deal about Denim Week I would have just skipped today. But that seemed a little defeated after the build up. And I have very specific posts I’m trying to get through this week. So anyhow I just decided better late than never. It all worked out. And we’ve enjoyed a restful evening.

  6. Love this post! But first, I’m so sorry about your plumbing issues. Not fun at all! Hope everything gets worked out without too many frayed nerves!
    So…these wide leg cropped jeans caught my attention today because I’ve just purchased a pair of NYDJ Teresa wide leg jeans (full length, not ankle). They’re way too long, so I need to hem them up. Now that I’ve seen you in the cropped pair, I’m wondering if I should hem them to an ankle length? I plan to wear them in Europe this fall, and hope the length I choose will go with both a fashion sneaker and a lug sole loafer. What do you think? Like a lot of us, I haven’t worn wide leg pants or jeans since my teens/twenties LOL I don’t know what shoes to wear with them and what length they should be! I LOVE these with your pumps and jacket, tho! So, so cute.

    1. Hi Annette, Guess what! I’m styling a pair of wide leg full length jeans for Thursday’s post. So hang on until then at least. The reason I opted to style wide leg crops and wide leg full length jeans this week is because I think a lot of women are ready to try them, but we’re all a little at a loss. So I’ve been doing my homework and trying things on in hopes that I can get it right for us. I’ll see you Thursday! Oh, and I am showing them in Wednesday’s video, too.

  7. When it rains it pours sometimes. Glad you got all your plumbing issues taking care of and able to continue on with your day, Love both your outfits and going to try and pick up a camp blouse. So pretty! Looking forward to the video tomorrow! Rest up when you can and I will see you tomorrow!

  8. Hi Kay…I so enjoy your blogs, photos, videos and scripture devotionals. Thank you for all of your efforts to help us ladies be who were were created to be
    as we move from one stage in life to another. Life is all about change. The fashion change currently is the wide leg pants and jeans which you have modeled well. I remain skeptical and uneasy about adopting that style. Perhaps my eyes will become accustomed to the look eventually, but at the moment I am not ready to transition to that look. Are you hearing this from others? Any words of wisdom? On another topic…I have recently lost 25 pounds on a healthy weight loss program. I let myself go during the pandemic with gaining weight and dressing poorly. I am grateful to have returned to a healthy weight, but weight loss has increased my facial wrinkles. I am 74 years old so already had my share of lines and creases! I need a good skin care regimen which may improve the looks of my face. I enjoyed your video on Proven and am wondering if it is something I should order. Are you truly content with the routine and benefits? I understand you represent the company and cannot be critical. Any comments would be appreciated. Blessings to you and your family. So sorry about your plumbing issues.

  9. The whole eight chapter of Romans has made a big impact on me. I did Bible study on Romans earlier this year.
    I have wide leg crop pants but not jeans yet. I tuck my top in or wear a shorter top that ends at the waist. Thanks for all your tips and your scripture verses and explanations.