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

How to Try a New Jeans Silhouette

October 9, 2023

This year you can wear most any jeans silhouette and be in style. While skinny jeans continue to look a little yesteryear, most every other style is considered very on trend. Still, it’s nice to try a new jeans silhouette every now and again. So today I’m sharing a few tips for giving a new style a real try while also sharing a classic fall outfit.

Herringbone Blazer with Wide Leg Jeans

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.

My personal preference in jeans is full length straight leg jeans. I like those that are fuller in the legs as well as the straight leg jeans that have a more slender fit. But I’m all for trying the more on-trend styles, and I especially think the fuller legs of wide leg jeans can feel great and be fun to wear. Here I’m wearing the Paige Sasha high waist wide leg jeans in the Stefania distressed wash. They’re available in a number of stores, but they all have a limited number of sizes at this point. See the caption below the next photo for links to the jeans.

Herringbone Blazer with Wide Leg Jeans
wearing size 30 (TTS) in the Paige Sasha high waist wide leg jeans at Nordstrom (and in black) // Saks Fifth Avenue // Anthropologie // Harrods // Paige // Shopbop // Revolve // AmazonMore Economical Option

In this post I’m wearing them with a favorite white button-up cotton shirt, the Willa herringbone blazer and brown suede pumps. But let’s make this post about more than this one pair of great high waist wide leg jeans. Trust me, I have struggled a bit with styling these jeans. But instead of throwing in the towel immediately and saying I can’t wear them, I leaned into them even more.

Trying a New Jeans Silhouette

Tips for How to Try a New Jeans Silhouette

  1. Try the silhouettes, washes and lengths that attract YOU.

Don’t be intimidated by the opinions of others. If you want to be fashion forward in your style, go for it! Truly, anything goes in denim these days. So if a particular style appeals to you, get up a little courage and try them.

How to Try a New Jeans Silhouette
  1. Set the new jeans silhouette up for success.

I always encourage women to try on any new clothes with their makeup on and their hair styled. Personally, I don’t even try on new shoes without my hair and face done. I know I won’t like what I see if I don’t give the new style a fighting chance. So put on some makeup, do your hair and try the new jeans silhouette with a top and shoes that work with them.

How to Try a New Jeans Silhouette
similar Tory Burch Kira bag and Kira camera bag

For wide leg, full length jeans I find that I need to wear either a slim-fitting top or at least one that fits close to the body at the waist. Otherwise the outfit will lack definition. Of course, another option is to tuck the top in to add that needed definition.

How to Style a New Silhouette of Jeans

Don’t forget to add a belt if needed. And put on some shoes that help you see the jeans in their best light. For wide leg, full length jeans I like to wear heels – such as pumps, mules or booties – or maybe a sneaker with a platform.

How to Style a New Silhouette of Jeans
  1. Try the new jeans silhouette with several different tops and completer pieces.

Every jean silhouette works differently with the various styles of tops and completer pieces. Some jeans look especially great with pullover sweaters while others seem to look best with tees or button-up shirts. For instance, if I’m going to wear a sweater with these wide leg, full length jeans, I’ll probably choose a close-fitting one.

Also some jeans look better with blazers, cardigans, bomber jackets or utility jackets than others. So swap completer pieces in and out until you see a combination you like.

How to Style a New Silhouette of Jeans

For these wide leg jeans I do like a blazer, but probably only one that has a little definition like this Willa herringbone blazer.

  1. Give your eyes time to adjust to how you look in your new jeans silhouette.

Don’t just try on the new jeans silhouette once; try them again and again. When my kids were growing up I would insist they try new foods by taking no fewer than three full bites. In the same way, I think we need to “really try out” new silhouettes, at least if we want our style to evolve and not get stuck.

How to Try a New Jeans Silhouette

I suggest trying on the new pair of jeans several times over the course of a few days. Do your best to look at yourself in the mirror with an open mind, a little optimism. Don’t immediately discount them. Understand that you are indeed going to look different in them.

Additionally I suggest using a few style hacks when wearing the new jeans. Even little things like rolling up your sleeves or adding a bold necklace can change the way your jeans look. For instance, I think this chunky chain necklace helps balance out the “visual weight” of these jeans. And the belt helps them look a little more anchored, in my opinion.

Herringbone Blazer with Wide Leg Jeans
high waist wide leg jeans at Nordstrom (and in black) – More Economical Option // white button-up cotton shirtmore economical option // Willa herringbone blazer // brown suede pumps (use code SARAHFLINT_CCLAURAKAY1 for 15% off full price purchase for new customers only) // chunky chain necklace // belt

Do you have to try a new silhouette of jeans? No. But wearing the most up-to-date styles in denim is one of the easiest ways to look a little more fashion forward. It’s a great way to keep your entire look more contemporary and stylish. And it’s really the only way to know for sure if something works for you or not.

I still prefer to wear straight leg jeans most of the time. But I’m glad I’ve learned how to style the wider leg jeans for my body. It gives me a little additional confidence and it gives me options. What about you? What silhouette of jean have you tried or will you try? I’d love to hear from you today.

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

Do you want to share your personal testimony of how the Lord has changed your life? But maybe you’re not sure how to do that. And maybe you’re afraid that your testimony will offend someone. I’ve discovered that if I simply share from real experience and a place of genuine joy and gratitude, then people are usually very happy to hear what I have to say. 

Let’s commit to share with someone this week what God has done in our lives. We can simply say with joy and enthusiasm, “I love the Lord because He hears my voice and my pleas.” We can share that we needed Him and He was there. We can tell others that we asked and He provided. When we give God the glory instead of ourselves, people tend to listen and be intrigued.

I love the Lord, because He hears
My voice and my pleas.
Because He has inclined His ear to me,
Therefore I will call upon Him as long as I live. ~ Psalm 116:1-2

xoxo, Kay
Join the Conversation

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

16 thoughts on “How to Try a New Jeans Silhouette

  1. Good morning & happy Monday Kay, I just wanted to tell you, I absolutely adore your site and look forward to your Wednesday YouTube video.
    I showed your site to my Talbots stylist and she was thrilled with your Talbots association.
    Have a great day🙂

  2. Hi, Kay,
    I am thoroughly enjoying your blog posts, videos, etc. However, I struggle with that third piece which really pulls an outfit together. My style essence is classic casual — I think. I have been a stay-at-home wife and mother for 40 years now. I have homeschooled all 11 of our children and keep the books for our business. I also now have 18 grandchildren. I have never felt completely myself in a structured blazer, but I do think they make an outfit look polished and complete. My go to stores are Talbots and JJill with a spattering of Nordstroms. Can you do another blog and/or video on that third piece? Thank you for your joyful and informative blogs and posts. I believe my daughters are impressed that I am up-to-date with the style trends, and even my husband “knows” you. 🙂
    God bless,

    1. Hi Mary,
      I always felt awkward and too done up in a blazer, but last fall I lucked onto one in a relaxed knit style at the thrift store. It was the perfect color and the fit was impeccable- crazy! I recently added an all season wool blazer in navy. That one has been harder to get used to – unlike my grab and go hoodie replacing relaxed blazer 😉 – but I’m working on it. Good luck on your journey.

  3. Hi There Kay Welcome back and gosh your week sounds like you will be busy . So huge Thank you for working hard to Inspire us I look forward to seeing your outfits always , and todays did not disappoint, I love Blues/Browns worn together and I love the ‘Wide Leg ‘ silhouette my favourite , as Im 5’ size 10 UK which I think is a 6 USA , like you Im an Hourglass with a defined waist , so I will be styling mine with the cardigan/sweaters new cropped length as they are perfect fit for us Petites Im Loving it! My new accessories are my Claret Belt and Ankle Bootees with a 2 and a half heel as I need the height with my Wide Leg Jeans . My other love is the Bootcut Jean as its another which makes me look taller . But Kay my Challenge is , to wear ‘The Straight Leg Jean’ which looks so good on you , but my last Straight Jean was a ‘Pepe Jean’ 35 years ago😱. So having a coffee with my friend this morning she has a new pair of jeans she has only worn once they are too short for her ( too long for me but ive put them into the Seamstress to take up) so thats Challenge 1. When I get them back and Style and Wear them Now for my other Challenge 2. They are BLACK !!!!! Im the lady who when I come onto your Blog I only wear NAVY 😂😂😂😂but like my friend said they won’t be next to my face and I must say Kay you are so right , when I tried them on and because they are a Solid Black they look rather Elevated ❤️. Loved your Devotional today too 💖

  4. Good Morning, Kay. I would ask for the DFMD community to pray and intercede for Israel. Please pray for their wisdom and protection, for all of those grieving over the loss of precious life, and those experiencing terror and turmoil throughout the Middle East.

  5. I sooo agree that we need to try a new style and really work with it before “dumping” it. Having makeup and hair done is so important. Like you, I already know an outfit will be a “no” if I don’t take the time for this. I’ll be wearing straight, ankle, bootcut and a slightly wider leg. Love my jeans. Have a great day!

  6. I have 3 pairs of straight leg jeans from last year that I love, after going to skinny to straight leg. I had trouble making this change. Not so sure of these wide leg jeans. I am short and have skinny legs, so not so sure these would look good on me. Are these Paige jeans considered trouser jeans? Very limited sizes in these. My straight leg jeans are from Paige and I just love them?

  7. Thank you so much for these tips, Kay. You look fantastic in this jeans outfit. The little things like a weightier necklace, a belt, and a more fitted blazer are the things that can help me get it right, but I would overlook those without your help!

  8. That’s such a smart looking outfit on you. It looks very pulled together and classy. I’ve found through experimentation that the high waist fuller jeans don’t work for my body. I’m 5’4” with a shorter waist and longer legs. I also have a bit of a bust so all of it put together just makes me look much much bigger than I actually am. (Size 4) The closest I have been able to get with this look is either boot cut, mini boot cut or the slimmer straight leg styles. I got so used to the skinny jeans and the tops and shoes to wear with them. Thanks for helping us try and figure out these new trends.

  9. Always love your devotion. I agree with everything you said in the post. You look great in the wide leg jeans. I went on board right away with the new jean styles. I have bootleg wide and flares. Maybe because I grew up in the 70s I am drawn to those styles. I never cared for skinny jeans. I wore my straight legs and slim straight. I might add I am 5’2. I don’t think the wide leg jeans or pants overwhelm me at all. (The wide legs I have are like yours not over the top wide like teenagers might wear.) It’s all about the right proportion. I read a book on petite dressing years ago that said petite women can wear any style as long as the proportions are right to your body. I wear my straight leg jeans the most because I can wear comfort shoes. I like wide leg jeans with a heel. I may finally get to wear my jeans since we got our first cold front.

    On a side note has anyone noticed the sales this weekend are not called Columbus Day sales anymore? Only my Christian friend who runs a consignment shop called it that. I wish retailers would stay out of culture wars and just sell their things. (I say this as someone who is sixty percent indigenous and rest European mostly Spanish.)

  10. You look fabulous in this jean silhouette. I love my jeans and am always looking for new ideas to keep them looking fresh and modern. When you advise us to put on make-up, and make sure our hair is styled, I could not agree with you more. I try to always do that too. If I don’t think I am looking my best it does not matter what I have on – I won’t like it. Or at the least I will not see its possibilities.

    Thanks again for a great blog

  11. I’m struggling here with Talbots high waist relaxed jeans in Salem wash. There seems to be a bit of excess fabric right below my “bum.” Is that the nature of these or are mine too big? What differentiates a relaxed fit from the jean that is just a little too big? Is a relaxed fit just a too big straight leg in disguise? Thanks for your help.

  12. Thank you! I just bought a pair of wide leg jeans yesterday at Chico’s. I will have to try them on several times with different tops/shoes to see what works. You post was timely for me.
    I always appreciate you!

    1. Your outfit looks great as do your jeans. I find that I just can’t justify buying anything but straight leg jeans, I’m glad skinny jeans are out as I disliked the feel of them. Having to keep up with jean silhouettes is expensive and challenging to find closet space. Straight leg jeans are a classic and look good so I’m sticking with those.

  13. Straight and boot cut have always been my friends, but I was SO glad to see the skinny jeans FINALLY go away! Whew! One style of jean I hadn’t tried was the full wide-legged jeans. I finally tried them after a you tuber with similar proportions to mine (read short, stout legs) tried some and looked great! Now I have a full length and a crop pair that I enjoy wearing. They aren’t my husband’s favorite on me, but I like them! They make me feel stylish and I usually get a complement or two!