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Elevated Jeans Outfits with Exquisite Comfortable Shoes

August 26, 2021

After spending a long day editing yesterday’s YouTube video, 8 Fall Outfits with 4 Pairs of Straight Leg Jeans {from 4 of your favorite brands}, can you believe I felt compelled to put together even more jeans outfits? Ha! But this time I wanted to create more elevated looks. Honestly, due to the state of things in our world, I’ve noticed that brands are definitely leaning toward more casual looks in their catalogs and showrooms. But I know that many of my readers and I still like to put on the polish every now and again. Plus, I have some new exquisite, comfortable shoes I wanted to share with you. So let’s check out the elevated jeans outfits I put together in my office yesterday.

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Elevated Jeans Outfits with Exquisite Comfortable Shoes

I’ve got LOTS to show you today! I went a little crazy with the photos. I can do that when I’m just using my iPhone for the pics. Anyhow, I’ll try to keep the copy brief. I hope you’ll soak up lots of ideas for creating your own elevated jeans outfits this fall. These are the kinds of outfits I’d wear to lunch with friends, dinner out, church, a meeting of some kind or even a doctor’s appointment (as long as I’m feeling well!).

Elevated Jeans Outfit with Flare Leg Jeans & a Casual Blazer

I created this first elevated jeans outfit with flare leg jeans I recently purchased from Madewell. Unfortunately, they’re almost sold out already. How’d that happen??? Oh my.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

While I’ve enjoyed wearing the crop length jeans, full length jeans will always look a little more elevated. But it’s hard for me to find bootcut or flare leg jeans long enough. I’m 5’8″, but I like to wear a heel with this jean silhouette. I just think heels always look best with flare and bootcut jeans, whether it’s a heel on a boot, sandal or pump.

But these flare leg jeans work for me here because I’m wearing my new Ally kitten heels. I’m an ambassador for Ally Shoes and they gifted me these exquisite kitten heels recently so that I could share them with you. They were very excited about introducing them because customers have been asking for a lower heel option.

Ally Kitten Pumps

Ally Shoes is a company founded and run by women who simply want beautiful heels that feel and look good all day long. I own three pairs of these shoes now, and I have to tell you they are the most comfortable heels I’ve ever put on my feet. And indeed, I can walk all day long in them.

Ally Kitten Heel Pumps

My kitten heels are in courageous caramel leather, but they come in colors and fabrications. And these simply elegant kitten heels also come in a full range of sizes from 4 to 12 with widths in narrow, medium, wide and extra wide. Because they’re made from genuine leather they will fit snug when you first try them on. But wear them for about 30 minutes and you’ll notice that they’ve already begun to grow and mold to your foot. You can use their “fit finder” located in the top right hand of their website to determine your best size, but they’ll also generously work with you to make sure you get shoes you love and love to wear.

Use my brand ambassador coupon code KAYHEELS to get $40 off first pair of heels (these kitten heels do count as heels) or code KAYFLATS for 10% off first pair of Ally flats.

Elevated Jeans Outfits

Another element that elevates this jeans outfit is my shirt choice. Add a collar and add class! I’m wearing my Talbots Perfect Shirt, also available in a bold and beautiful wild aster. It runs true to size for a tailored but soft fit. I cuffed the sleeves up over my blazer cuffs for a little extra style.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

I also added polish with a leather belt (similar), a gorgeous silk scarf (more on that later) and simple but elegant jewelry. I’m wearing this Wilder Necklaces from Gorjana and the pearl hoop earrings I wore in yesterday’s video. These are not the same, but similar. And these hammered square pearl drop earrings are another nice option.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

Finally, my casual washed blazer in jungle green is indeed casual. But the longer length, the dark color and the simple fact that it is a blazer yields an elevated style choice. Remember, a key to creating elevated looks with jeans is to blend and combine both casual and dressier elements for a beautifully, eclectic vibe.

Elevated Jeans Outfit with a Relaxed Blazer & Silk Scarf

I created the next polished look with my Everlane Way-High Jeans. I purchased these back in the winter and they are still some of my favorites. I haven’t worn them much this summer, of course, but I’m anxious to pull them out again for fall. They have a fuller leg with a slightly ballooned shape. But the way-high waist and the raw hemline are what really set them apart. They’ve recently restocked the Way-High Jeans and they’re available in a darker wash, a lighter wash, black and a pale green. I’m wearing the size 30 very comfortably.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

This time I topped my jeans with a simple v-neck white tee, but I carefully chose one that has a more polished appearance. Then I topped that combo with my J.Jill easy tab-sleeve blazer, featured in yesterday’s video. I love it when you can get both comfort and polish out of a garment, and this blazer delivers on both counts. While the blazer has a relaxed vibe, details like the bust darts, tabbed sleeves and gold buttons raise the style quotient considerably.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

Again I just draped this beautiful silk scarf just inside the jacket lapels. Maybe I should go ahead and share about that scarf with you.

I’ve also been asked to be a brand ambassador for Sarah Flint shoes. Sarah is a beautiful young woman with exquisite taste and a savvy business acumen. She creates lovely, Italian leather, hand-crafted shoes and sells them directly to the consumer, bypassing the middlemen that so often cause the prices of such luxury shoes to go beyond reason. Yes, these are investment pieces, and the cost reflects that. But my oh my. You do get what you pay for.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

After receiving my first pair of Sarah Flint shoes, I actually turned right around and purchased the Natalie flats I wore with this outfit. I did not even hesitate. All Sarah Flint shoes feature extra padding in the sole, non skid rubber foreparts on the bottom of the shoe and amazing craftmanship. Again, these shoes are designed to fit snug when you first put them on, but they quickly “grow” around your foot. You’ll feel like they were designed just for you.

You won’t believe the noticeable padding inside these shoes!

You can use my ambassador code SARAHFLINT-BAKAYH to save $50 off your first pair of Sarah Flint shoes.

Anyhoo! Sarah also features other beautiful accessories and gifts in her online shop, such as this 100% silk, handmade in Italy Folklore Forest scarf. I had some Mother’s Day gift money sitting to the side and decided to use it to purchase this memorable and beautifully versatile scarf. But of course you can replicate this elevated jeans outfit with any beautiful scarf you already own and treasure.

Silk Scarf with Blazer

I guess the only other thing I added to this look is my Coach Turnlock Clasp Satchel that I purchased in the Nordstrom Anniversary Sale. I’m loving the versatility of this bag. And anytime you opt for a structured bag, such as this one, instead of a more relaxed one, you raise the style quotient of your jeans outfit. It doesn’t have to be an expensive designer bag either. For instance, this one or this one would work just as beautifully. However, I don’t mind investing in a quality handbag that I’ll carry for years.

Elevated Jeans Outfit with Straight Leg Jeans & Field Coat

Lest I lead you to believe the only way to elevate a jeans outfit is with a blazer, I created the next outfit with my sand castle colored cotton twill field jacket, also featured in yesterday’s YouTube video.

Straight Leg Jeans and Field Jacket

While the field jacket is a more casual silhouette, it still has a lot of structure and finesse. And I think by wearing it with my pointy toed Natalie flats and Folklore Forest scarf I achieved that elevated look.

Elevated Jeans Outfits with Exquisite Comfortable Shoes 18

You know, I know that neither the Ally Shoes nor the Sarah Flints will be for everyone. But I did want to introduce them to my community in this post because so many women do indeed need good quality, comfortable shoes.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

This time I draped the Folklore Forest scarf on the outside of my field jacket. Of course, there are so many ways you can tie a beautiful scarf.

Elevated with a Silk Scarf
Straight Leg Jeans

My jeans in this look are Talbots’ straight leg jeans in the Shore wash. Even though these are the regular misses length (not tall), they were too long for me. So I cut them off last spring with my sewing sheers, leaving a trending raw edge. They work perfectly with flats, but I can still wear them with heels and booties, too.

Elevated Jeans Outfits with Exquisite Comfortable Shoes

I think the only other thing I added in this look is my Nordgreen Native watch. Of course, adding a watch is always a simple but elegant way to elevate an outfit. (Use code KAYHRMS for 15% off your purchase at Nordgreen.)

Elevated Outfit with Black Jeans & Flats

For my final look I switched to my black jeans. These are my Everlane straight leg black jeans, but they are sold out. But of course you can duplicate this look with any pair of black jeans. I hear great things about the Original Cheeky Jeans at Everlane, and they do have some in a black wash.

Elevated Jeans Outfits with Exquisite Comfortable Shoes 21

I waffled back and forth on what t-shirt to wear here, but I finally opted for the black twist neck tee (similar). You know I love all black, but you could create similar outfits with either a splash of color in the top or another neutral.

But I thought it would be snazzy to create a column of black under my sand castle colored cotton twill field jacket . Doesn’t that look great?

Elevated Jeans Outfits with Exquisite Comfortable Shoes 20

My Sacchetto ballet flats in black nappa leather are the shoes Sarah Flint originally gifted me. They quickly won me over to these exquisite, comfortable shoes. This is how comfortable they are: This was the last outfit I shot this afternoon around 3 o’clock, but I haven’t taken these shoes off yet…and it’s after eight as I wrap up this post. I could have changed back into my house slippers or a par of flip flops, but I just didn’t need to. These ballet flats feel that good.

Elevated Jeans Outfits with Exquisite Comfortable Shoes 22
Obviously I didn’t have my glasses on when I took this photo! I should have dusted them off. They are the most gorgeous patent and nappa leather.

Wearing all black is always a great way to elevate your style.

Elevated Jeans Outfits with Exquisite Comfortable Shoes 23

Well I hope you enjoyed today’s post and got a little style inspiration. I wanted to put together elevated jeans outfits that you could wear most anywhere. And, depending on your work environment, I think all of these make great work outfits…or at least casual Friday looks. And with that in mind, I also wanted to take this opportunity to introduce you to Ally Shoes and Sarah Flint. It does no one any good for me to have all this information about these outstanding shoe brands and not share it with you. If you’re looking for comfortable shoes for work or other nicer occasions, I definitely suggest you check them out.

For Sarah Flint Shoes, shop HERE and use code SARAHFLINT-BAKAYH for $50 off your first purchase.

For Ally Shoes, shop HERE and use code KAYHEELS: $40 off first pair of heels; KAYFLATS: 10% off first pair of flats.

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Do you trust the Lord? Completely? Do you trust that He is still in control, that nothing has taken Him by surprise? If we really believe that God is sovereign, we will not be anxious as we watch the evening news or read the morning paper.

As my husband and I were talking over the events of recent days this morning, he quoted someone he had been listening to on a podcast as saying, “Things are not falling apart; things are falling into place.” I don’t know why, but somehow that brought me comfort. It reminded me that with God it often appears that things are falling apart, but in fact God is working all things together for our good.

I know that you can do all things;
    no purpose of yours can be thwarted. ~ Job 42:2

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xoxo, Kay
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52 thoughts on “Elevated Jeans Outfits with Exquisite Comfortable Shoes

  1. A jacket really updates and makes a simp,e pair of jeans look “workwear ready”. Love the leather kitten heel shoe.


  2. Kay, love the look of the Talbot’s straight leg jeans in the Shore Wash. But you said the Misses Regular length was too long, so long you cut them (which does look cool BTW). I’ve read that you are 5’8″. . .can you state what your Inseam length is? I was considering ordering a Long–because my legs are 34″, and I’m 5’9″. But if the regular is really that long, not sure what to do. I seriously wish the stores would carry a few samples in Long so we could get a feel for the fit before ordering!

    1. Hi Katie. For jeans that should hit right at the top of the foot (to wear with flats or boots) I prefer an inseam of 29-30″. If I’m wearing flare leg or boot cut jeans I like 33″ because I always want to wear those with heels. But I wanted these Talbots straight leg jeans (they have an inseam of 31″) to be a length where I could wear them well with flats and sneakers, as well as shorter boots, without puddling on top of my foot. So I cut them off probably an inch and a half. From crotch to just below ankle bone I measure 29″ and from crotch to floor I measure almost 32″. Hope that didn’t just muddy the water!

  3. Kay, those shoes (all of them) are BEAUTIFUL! But the price! They must be super comfortable, but I have never spent over $100 on a pair of shoes. Most shoes are never very comfortable after a couple hours for me. I’m a size 10 1/2 – 11 medium with no arch. Oh, except UGGS I can wear all day long hah!

    1. As I said, I know they’re not for everyone. But I’ve found that we all have our “thing” we’re either willing to spend more on or NEED to spend more on. Some of my readers prefer to have a few pairs of great shoes while others opt for more footwear at lower price points. I’m not trying to push one thing or the other. I just wanted to share the information and coupon codes I have. The way I see it, if a woman with problem feet is still in the workforce and having to wear nice shoes all day every day, she probably will want shoes that fit and flatter and that are functional for her feet. I’m just trying to provide options and information.

    2. Peggy, I find no in my mid-fifties ith foot problems that I can’t not spend over $100.00 and get a comfortable dress shoe or even a tennis shoe that’s great!!

  4. That sounds like the PERFECT place for you to volunteer, Kay! You will be a blessing and be blessed among those women. I LOVE all of these outfits. Great inspiration. I never know whether to tuck a collared blouse in or leave it out of a blazer. How do you decide?

    1. I think you can absolutely do either – tuck or leave out – especially if the shirt is fitted, like this one is. But I generally try it both ways and then go with what I think looks best. And when I wear a shirt under a blazer, I almost always tuck the shirt because the blazer is hiding any muffin top effect anyhow. I’m glad you enjoyed the post. I’m really looking forward to visiting the Dress for Success shop today.

      1. That is helpful Kay, regarding the shirt tails. I was not clear in my question, and actually I was referring to the collar of the shirt….inside the blazer/jacket or pulled out on top of the blazer/jacket??

        1. Ahhh. Sorry about that. It’s been a crazy busy day and I’ve been answering these comments while darting in and out of appointments. I generally try to flip the back of the collar up if it will stay that way. Then the front tabs just naturally sit up a little higher. That’s my preference. Otherwise, I play around with it a bit. I think they look best just naturally staying inside of the lapel of the jacket. But if they need to come out and sit on top that’s an option, too. I think it really just depends on the size of the shirt lapels, etc.

  5. Have you tried NYDJ jeans for length? I’m 5’4″ and they are WAY too long on me. You might like their bootcut style. I love that you style looks that are classy and appropriate for women our age!

    1. Hi Lori. Yes, I tried the NYDJ. I bought some in the Nordstrom Sale, but I ended up sending them back because they just weren’t quite long enough to wear with heels. Thanks for reading. I’m so glad you enjoyed the post.

  6. Great inspiration as we transition between seasons! Thank you for the hard work and thoughtfulness that went into this. Also, thank you for the inspirational message. When we can’t trust our leaders it’s good to know we can always trust Our Leader who will NOT let us down.

  7. I do not receive nearly as many clothes for free as you must assume. In fact, I receive very little for free. And everything I do receive for free I immediately donate to either Dress for Success or another charitable organization, or I gift it to a friend or family member. Also, this is my job. I style clothing for a living. I am not wasteful or extravagant. It may appear to you that I have an abundance of clothing, but in reality my personal wardrobe fits into a very normal size closet that I share with my husband. I do not appreciate your lecture. I would never presume to lecture you in such a way.

  8. Good morning, Kay. I love the way your styled the scarves with the jackets/blazers; looks very pulled together!
    Needed to read the Blessed for My Day, too, especially with all the news today.

  9. Really enjoyed these elevated style outfits. The scarf and shoes are particularly beautiful. I know that you will be an inspiration at Dress for Success. Thanks as always.

  10. Your choices today were so attractive. Thank you for balancing your outer beauty with the inner beauty from your faith ! Your sweet spirit shows as you post and give us snippets of your day.

    My question is : Would you suggest the slim ankle or the straight leg from Talbots? I am not wanting to buy two pair. I did buy the everyday relaxed, deciding between size 4 and 6.

    Enjoy your day, Kay.

    1. Hi Barbara. If you’re considering the jeans for wearing into winter I would probably opt for the straight leg jeans. They’ll be good for year round really.

  11. I loved the quote about things falling into place. I’m at a point in life where I’m trying to buy quality and buy fewer items so I appreciate your recommendations. I have many lovely scarves, so I am glad for the scarf suggestions. I’ve been following you for a few months and used the word “elevated” in a conversation the other day. My daughter said she never thought I’d use that word. We had a little laugh.

    1. Hahaha! I get it. I use that word a lot more than I ever did before. Maybe I need to look through a thesaurus for some alternatives! ?

  12. Thank you for all the hard work you put into your blog. I understand that not all the items you show us are going to be in my price range. That’s okay. You give us options, show us new websites where we can browse, guide us through current trends. I appreciate your openness and positivity. It’s sad that some people respond to your work with personal attacks. That’s not warranted and comes across as judgemental. I agree with your response.

    1. Thanks so much for your kindness and encouragement, Susan. That means a lot to me. I probably shouldn’t have even approved that comment for display, but I don’t want to be guilty of censorship either. I figure it all speaks for itself in the long run. And I’m pretty confident at this point that I’m providing some value, and I love what I do. So it takes more than a rude comment to throw me off. I sure do appreciate you ladies!

  13. WOW, how RUDE! Many of us appreciate these posts. Who are you to decide what “enough” is? I think if you saw my closet your head would explode! Hahaha. But it brings me JOY, which makes me bring joy to others. You sound like you could use a little of that yourself. Maybe go buy yourself a beautiful scarf or something? Sheesh. Doesn’t look like that “spiritualism” you speak of is working for you. Me thinks your envy is showing.

    1. Colette, hat are you upset about? I couldn’t see anything in Kay’s post that ould offend?! hat made you so upset!!?? Concerned!!

    1. Thanks Ginger. It was fun putting these together. Now if we could just wear them! It’s so blasted hot here today. Well actually all week it has been. I’m ready for some relief. I know you must be, too!

  14. You won me over, Kay. I have plenty of shoes, but I recently purged my closet of the things that don’t fit me or my true lifestyle (thanks to a video you did back in February!). Gave a lot of thought to my colors, my style, my daily activities… and used a gorgeous scarf as inspiration to rebuild (based on another fabulous blog – The Vivienne Files)… today I bought the Ally Kitten Heels in LIME GREEN!! I know they will go with at least 50% of the outfits I will wear and will work for my lifestyle, elevating jeans or brightening up a straight skirt and blazer look. I appreciate your efforts to show us new looks and ways to stay modern with what we have.

    One thought – the long blazer with the Everlane balloon jeans looks a bit out of proportion to me – I wonder how a high-hip length blazer might look?

    1. Wonderful! And how fabulous that you took the plunge and got the lime green. I think that is so inspiring. You obviously have spent some time defining your style and now you’re owning it. I love that! Thanks so much for sharing.

  15. Kay, this was a great post today. It’s obvious you put a lot of work into it. I especially appreciate it because I wear jeans more than anything else as the weather turns cooler. These ideas allow me to put outfits together with items that I already have in my closet.
    I’m not a scarf person but the scarf that you showed is absolutely gorgeous and I am seriously considering it.

    1. Thanks Juliet. I’m glad you enjoyed the post. These kinds of posts are a lot of work, but they’re my favorite kind to do really. I feel like they offer such value. And I really do want you ladies to feel like you get some value when you visit here.

  16. Thank you for introducing these beautiful shoes! I do need a couple of pairs of comfortable dressy shoes, and I know I have spent thousands of dollars over my lifetime on shoes that I can’t enjoy wearing. I am trying to pare my closet down to fewer but more functional pieces and I appreciate all the good tips I find in your blog.

    1. Thanks Carroll. These are definitely investment shoes. And I couldn’t fill my closet with them. But I know some women really do need quality footwear. And I’ve just gotten to the age where I’d much rather have a few versatile pairs of shoes that feel good and look fabulous rather than dozens of shoes I don’t really enjoy.

  17. I knew everything when I was 12. I told a next door neighbor she was doing something wrong. . She looked at me with a smile and said, “You might be right but thats’s the way I do things for now”. Best lesson I ever learned.
    I love this look. I can go anywhere dressed like this around town. We wear long cardigans a lot too. Which reminds me. I need to shave a cardigan.
    Loved BFMD!❤️

  18. I absolutely loved every outfit you showed here. I am a big jeans person since I’ve retired from the corporate world and I have struggled at times to elevate my jeans look without looking too dressed up. I like the way you balanced all of the looks in that regard. Please disregard that horrible, negative comment. You actually helped me see my own clothes in a new light by putting together items that I would not have thought of. And that means I can buy less, if I want to.

    1. Wonderful to hear Donna. I know I have to walk a fine line at times when it comes to price points and what I share. But with over 12,000 subscribers at this point, I’ve got women here from all walks of life who are looking for different things. So I’ve decided to share what I can and trust that you ladies are mature enough to sort through it for what works for you. Most are, some aren’t. But I’m very grateful for this gracious, beautiful community of women.

  19. Kay, I value your advice about clothing so much and look forward to your BFMD lessons. Your posts are sensible: you show us how to create lovely outfits and help us to plan our wardrobes with the least amount of waste.( both in garments and in budget)It is evident from your posts that you invest yourself in all that you do. I love that you share your faith with love and compassion. I am thankful that I happened upon your blog; you have made a good difference in my life.

    1. Oh Suzanne, that is so kind and encouraging. Thank you so much for letting me know. You ladies are such a blessing to me, too. Thank you for being here and for taking the time to comment.

  20. Kay, Thank you !!!!!
    You have helped me so much over the last months since I found your site. Finding Talbots has been such a blessing for me as I need to wear a petite top or dress. I never realized that before. I would shop and never have success with what I bought if I could find something I even liked!
    I have watched many other “YouTubes” on this subject and just couldn’t seem to pull anything together. My wardrobe is still a work in progress, but I now can enjoy being an older woman who is a “modern” woman! comfortable in my clothes. I also just received my first T-shirt from Sadie and Jane and I just love it. I got the butterfly with the Romans scripture. It is so soft and of great quality.
    Also, the news has been very distressing but it is a comfort to know that God is working all things together….

    1. Yes! I’m sitting here watching the news right now. And I’m reminding myself that God is not mystified by all of this. He is good and trustworthy and ultimately in control. I’m so glad my blog and YouTube channel have been helpful to you. And that you have found a brand that works for you. Thanks for letting me know. ?

  21. Kay : Greetings from a Cincy based fan of your blog. All the outfits look great on you. Thank you for sharing your time to bring styles and products that your readers may enjoy and for always being so genuine .

    I believe Sarah Flint shoes are/ were a favorite of the Duchess of Sussex so you are in good company!
    I have wide feet ( C or D US ) and like to have good arch support for comfort . European made- shoes generally don’t have the wide widths that I need. Any input about width of the Sarah Flint shoes would be much appreciated.

    1. Hi Sharyn. Thanks for sharing. Yes, quite a few famous women have worn Sarah Flints. I don’t think they come in wide sizes but I can tell you that the ones I’m wearing here have really stretched to the shape of my foot nicely. They’ve not stretched out to the point that they’re too big. They just feel really nice on. However the Ally shoes I showed in yesterday’s blog post do come in both wide and extra wide sizes. So you might consider those. I’ve found them to be very comfortable too.