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Styling High Waist Flare Leg Jeans

January 29, 2020

Hi there, and welcome to Dressed for My Day. My goal here, with each and every post, is to inspire and help women like you and me to dress beautifully and appropriately for our unique days so that we can engage gracefully and authentically with our worlds. Today I’m sharing a Valentine’s Day appropriate outfit in which I’m styling high waist flare leg jeans.

The trending jeans

The way I see it, part of my job here, in this little corner of the blogosphere, is to keep you and me up-to-date on fashion trends. And remember, trends are not just those items or accessories that flash in to the fashion world and hen fade quickly. Those are fads. And we can take them or leave them.

But a trend is better described as the direction fashion is going. And if a trend picks up momentum and really takes off, we’ll end up looking dated and out of step if we don’t know how to work that trend.

Styling High Waist Flare Leg Jeans

While you’ll definitely still find skinny jeans and slim cut jeans on the racks and in fashion-forward outfits, jeans are trending toward wider leg openings these days. We’re seeing more and more straight, wide leg, relaxed fit and flared silhouettes.

Styling High Waist Flare Leg Jeans

So you probably don’t have to wear wide leg or flared leg jeans if you don’t want to. But having a pair in your wardrobe will give you the opportunity to appear a little more fashion forward if you’d like. Plus, I find these particular jeans amazingly comfortable.

How to Style Them

I’ll get into the details of my outfit in a bit, but first here are a few tips for styling high waist flare leg jeans:

  • Select jeans that fit you well {snug} in the torso. In order for the silhouette to look flattering, you don’t want the jeans sagging or bagging up top.
Styling High Waist Flare Leg Jeans
  • Wide hems on these jeans look modern and more interesting than the basic 1/2″ hem.
  • Steer clear of wide leg flare jeans with a lot of whiskering or patches of fading unless you are comfortable with drawing attention to those areas of your body. A consistent wash will create a longer, leaner silhouette.
  • To create a balanced silhouette, either tuck your top in (partially or completely), belt it (inside or outside the jeans) or wear a fitted top. Don’t wear a blousy, full top that is not tucked in or gathered at the waist.
Styling High Waist Flare Leg Jeans
  • While the preferable length is just 1/4 to 1/2″ off the floor, we’re seeing these jeans worn higher off the floor this year, especially with modern, chunky boots or sneakers. But remember, the goals is to create a long leg silhouette.
  • To create the longest leg, consider wearing pointy toe heels, boots or flats with these jeans. But, again, we’re seeing more platform sneakers with these trending jeans, too.

Outfit details

Valentine T-Shirt

My light wash jeans are from Talbots, but they also offer these jeans in a darker wash. I think they run a bit small. I generally wear a 6 in Talbots jeans, but I’m wearing a snug 8 in these. That’s the way they need to fit, so I’m fine with that. But definitely go up a size from your usual Talbots jean size.

This darling red 3/4 length sleeve Dalmation t-shirt is also from Talbots. I’m wearing a medium. With the heart-spots on the dog, it will be fun for Valentine’s Day, but I think you could definitely wear it past the 14th. This look would be great with a white or dark denim jacket over it.

Styling High Waist Flare Leg Jeans
Dalmation t-shirt // high waist flare leg jeans // suede booties (similar) // belt // handbag (no longer in this color) (more economical option) // earrings // sunglasses

If you’re a Classic Awards member at Talbots, you can get 25% off regular-price merchandise right now with code STYLE25. You’ll also receive 100 Bonus Style Points (one time only) on a transaction now through February 5th.

Thanks so much for stopping in today to check out how I’m styling these high waist flare leg jeans. I really like the way these jeans fit and feel, so you’ll be seeing more styling ideas with them in the future. Let me know if you have any questions.

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Blessed for My Day

Honestly? That’s the question we need to ask ourselves as we approach God in worship. Whether we’re meeting our Creator one-on-one in a quiet place or approaching His throne in corporate worship with other believers, we need to make sure we’re being honest with Him. God requires transparency if we’re really going to grow in relationship with Him.

Yes, God already knows the thoughts in our minds and the intents of our hearts, but He also desires us to be open and vulnerable with Him. In fact, God’s Word tells us over and over that He detests pretense and hypocrisy. So the next time you approach God – whether it be in a simple mealtime prayer or while you’re walking alone – pause to commit to total transparency first.

God is spirit, and those who worship him must worship in spirit and truth. ~ John 4:24

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xoxo, Kay
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26 thoughts on “Styling High Waist Flare Leg Jeans

  1. Love reading your post everyday. Your devotions always inspire me and I enjoy all the fashion advice.
    Now for my question, I have a pair yellow mustard colored cotton paints . What color shoes do I wear with them? In the fall I wore printed black top and black shoes but wasn’t sure. I would appreciate your help.

  2. Kay, you look amazing in this outfit. You should submit this look to Talbots ‘Share Your Style.’ I love the jeans but I am not tall or slim. Guess I should go to the store and try on this style. Still thinking of you and Benji. May God bless you and give you comfort.

  3. That shirt is adorable! The jeans look great on you too, I’m a bit on the short side so next time I’m in the store I’ll have to try a pair on to see what this new trend looks like on me.

  4. I love the wide leg jeans when I see them in someone else. I own a pair but every time I put them on, I end up taking them off. I can’t wear heels due to my knee pain. But I’m going to try to shorten them and wear them with pointed flats. And speaking of my bad knees, here is my fashion question.
    I am a professional seamstress and work from home. I dress in a professional casual style on a daily basis because I have customers coming almost everyday. I work on wedding dresses and feel it’s important that I put forth a professional appearance. Recently, my son, a physical therapist, has been working with me and my knees. He has stressed that I stop wearing my cute shoes and boots while I am working. I need to wear a specific athletic shoe. So I have ordered a couple of colors. Now I need help styling them with my wardrobe. I typically wear nice skinny dark jeans with dressy sweaters and tops. .

  5. Kay, You look great in this outfit! You did a great job at creating a long lean line! I so agree that our jeans need to fit us well, no matter the brand we wear. I can’t stand for my jeans to bag or wrinkle below my backside. I have a pair of bootcut jeans. What is the difference between flare legged and bootcut? Oh, I could use some extra prayers around 2 GA time today. I have having a couple of facet injections done in my spine to try and treat arthritis, and I’m a bit nervous. Thanks! Have a great day!

  6. Great outfit! I am short, but have always thought that wide leg or flare leg jeans add ‘height’ to my short frame! I’m happy to see them again!! The Dalmation t-shirt is so adorable!!

  7. I need some suggestions for shoes in a wide width that don’t look “old lady”. I have a dickens of a time trying to find wide width shoes in more moderate prices. Many times the’re only available on line. The DSW store near me has only one pair in wide and they are a Sketchers in a wide width. Can you help??

  8. Kay, Love this outfit on you. So glad bootcut and wide leg jeans are coming back. For me so much more flattering and much more comfortable.

  9. I’m a pastors wife who has a heart for young mama’s. Do you have a light devotional guide I can use when I invite a small group into my home?

  10. Kay, you look great in this outfit! Ok, so I’m 5’1”, short waisted of course. Should I tuck my shirt and wear a belt? I do not like the front tuck, especially on me. I’ve ordered some wide leg cropped jeans. I have a dressy pair of pants in this style from WHBM. And I like them, so I’m anxious to see if I like the jeans. Thanks for all you do?

    1. I’d just play around with it a bit. Try tucking or wearing a top that ends right at the waist. You want your legs to look longer, so that’s why I suggest tucking. But just play with it, take some selfies of different pairings and stylings and see what creates the most proportional look. I hope you enjoy them.