Styling Demi Boot Crop Jeans for Spring

Happy Monday ladies. I hope you had a relaxing weekend! Ours was mellow so I’m ready to dive into the week. Let’s kick it off with some uplifting color and a simple, classic pattern. Polka dot is one of those timeless patterns that’s stood the test of time, yet never looks stuffy. They’re always chic and look modern which makes them perfect in my book! Today I’m styling a classic polka dot sweater with some slim, demi boot crop jeans.


jennifer of a well styled life wearing hat and green polka dot sweater


Crop flares? Yup, but these are not what you expect. I’ve learned to ignore the labels that brands put on their garments.


If we get hung up on the name it might influence whether you’ll try something on. These jeans are called a slim, cropped, demi-boot which is totally out of my comfort zone. If I was adamantly avoiding boot-cut jeans, I would have passed on these, which would have been a shame because I love the fit. Madewell says they’re cropped, have a straight leg with a subtle flare at the bottom. But to be honest, that ‘demi boot’ is so slight they seem almost straight down to the ankle.



These are made from Madewell’s “comfort stretch” denim which is cotton/elastane and stretches a bit more than no-stretch jeans. And because they have less elastane than other jeans, they’re less likely to bag out when you wear them. I like that Madewell rates the stretchiness of their denim so you know just what you’re getting.  See their chart below.


madewell denim stretch guide

These jeans have a nice high rise and are fitted through the hip and thigh. They’re available in regular, petite, and tall. I’m wearing the regular and at  5’4″, they’re just ankle length. Have all these options allow you to dial in the exact length you like.


The pale wash is super casual and great for spring. These jeans would look great with a crisp white shirt, leopard print belt, and classic loafer…or a pretty blouse, and espadrilles, with a stretch linen blazer …or dressed down with white sneakers and a striped tee.



This fun sweater is a cotton blend with a cheery polka dot print on the front and back. The website says it’s a black polka dot but it appears closer to deep indigo to me. Frankly, if the color is that indistinguishable, does it really matter? Not to me. The green is on the cool side…closer to mint. It has a bateau neckline and 3/4 sleeves which you know I love for spring. It’s in sizes petite, regular, plus, and plus petite. I’m wearing a small petite so it runs TTS.

This sweater would also look great with white jeans, a denim skirt, soft chinos, or Bermuda shorts when the temperature warms way up.



I’ve been on the hunt for a new straw hat, ( I am obsessed with summer hats), but to be honest, this one fits the bill for me every time. It’s got a wide enough brim to keep the sun off my face and its totally classic shape goes with everything. Brixton makes this same shape in wool as well as a bunch of different colored straws. The weave is rather rustic which makes it very casual. I think many women would like to wear hats but they buy ones that are too dressy for their lifestyle. Look for ones with larger weaves and less frou-frou detailing which is more appropriate for daily wear.



My sunglasses are classic Ray-Ban Wayfarer that I’ve owned forever. I go for polarized at every opportunity because it cuts way down on the squinting and we all know that squinting increases wrinkles. 🙂 Crow’s feet are one thing, but the 11″s between my eyebrows are something altogether different and I hate to make mine worse.


My sandals are a perennial favorite and best seller so Gentle Souls makes them every year.  They’re one of my go-to brands for stylish shoes and sandals that are comfy for my aging feet. They have an adjustable velcro ankle strap that keeps them securely on my feet plus a signature flaxseed-cushioned pillow in the footbed. My pair is at least 4 years old and they’re holding up beautifully.

I kept my jewelry simple for this look with a (vintage) large silver bangle (similar) and silver drop earrings that have a faceted orb of green Amethyst suspended in a silver teardrop setting. They look like a giant green polka dot!

Are you a fan of polka dots?

Let’s make it a great week ladies and remember to wear what makes you feel confident.


This post may contain affiliate links which won’t change your price but will share some commission.


  1. Kate Granado
    April 5, 2021 / 5:35 pm

    Excellent outfit to begin a new week! You looked great. And love the hat. I live in the land of the Panama Hat | Ecuador. Our original Panama Hat did not have a wide brim. Fortunately, you can have hats made here to your own specs. I’m on the hunt right now for a wool hat. We’re heading into our cooler season. You mention a wool hat. I’ll pop on the website and take a look. The dots are fab!

    I love your blog and your lovely “up-beat attitude. xok

    • Jennifer
      April 6, 2021 / 8:39 pm

      Welcome, Kate!!

  2. Deb
    April 5, 2021 / 4:00 pm

    I love your whole look, Jennifer. I would wear every piece!

  3. Cathy
    April 5, 2021 / 12:15 pm

    Hi Jennifer,
    Cute look today! I love wearing hats but have an issue with “hat hair” when I go inside. How do you handle that problem?

    • Jennifer
      April 5, 2021 / 3:57 pm

      I leave my hat on:)

  4. Ilo
    April 5, 2021 / 12:14 pm

    I definitely love the jeans. If they are wore shorter, that small flair keeps them from staying up when you stand up. I love crops, but I don’t want to be pushing them down when I get out of a seat. And I like polkadots. I have a few new tops with them. Thanks for modeling everything.

    • Jennifer
      April 5, 2021 / 3:59 pm

      That ‘staying up after you sit’ is why I am moving away from skinny jeans

  5. Kay
    April 5, 2021 / 11:08 am

    I have always loved polka dots. It’s nice to see them moving away from strictly white or black dots on a given color.

    • Jennifer
      April 5, 2021 / 11:52 am

      I agree. That’s one of the reasons I liked this top! A pretty green

  6. Canadian Elizabeth
    April 5, 2021 / 10:51 am

    As usual, you look fabulous Jennifer! What amazes me is how well the mint colour goes with your jeans. I would never have thought of that colour combo.
    A question…what is the shoe product you use to stretch out tight fitting shoes? Can you explain how to use it & and whether it’s available in Canada? Many thanks!

    • Jennifer
      April 5, 2021 / 11:54 am

      I just buy shoe stretch spray. When it runs out I refill the spray bottle with rubbing alcohol and water. Then I either cram shoe trees inside or put two pair of socks on and jam my feet into my shoes until they dry.

  7. Eve
    April 5, 2021 / 9:50 am

    I agree, it’s hard to see the flare. I like these a lot and the shirt with the black sandals is perfect. I have polka dot in black with white dots and navy with grey dots, I really need to lighten up my background colors. You look super in this color,

  8. Paulette Levy
    April 5, 2021 / 9:42 am

    A great fit and totally pulled together look! Love your polka dot top, love the jeans too. And your hat is so much better looking than mine is. Have a super Monday!

    • Jennifer
      April 5, 2021 / 11:54 am

      Happy Monday my friend! Xx

  9. Francesca B.
    April 5, 2021 / 9:18 am

    This is such a beautiful look Jennifer; my daughter keeps telling me to go to Madewell for jeans and now I have too! Fantastic post thank you kindly and have a happy week.

    • Jennifer
      April 5, 2021 / 11:55 am

      She’s right 🙂 You need to try then. I love Madewell jeans.

  10. Linda Henderson
    April 5, 2021 / 8:38 am

    Cute! Love the look.

  11. Leslie
    April 5, 2021 / 8:31 am

    I love this look from head to toe. Hats are must for me whenever I’m outdoors, particularly here in Texas where the sun is intense for much of the year. The mint green (one of my best colors) top with polka dots is fresh and spring-like. All in all, a winning look!

  12. Claudette
    April 5, 2021 / 7:42 am

    What a delightful outfit you are wearing today. The sizing is perfect and the color of the sweater looks nice on you. thank you.

  13. MRSBEN2
    April 5, 2021 / 7:37 am

    I am really loving your new hair-do Jennifer! As to your outfit and rather than repeat; agree, so perfect in every way.

  14. Lin
    April 5, 2021 / 7:33 am

    I am a big fan of polka dots.
    Your complete outfit is adorable. That mint green is perfect in you.

  15. Jo
    April 5, 2021 / 7:23 am

    I love, love, love today’s look… casual & comfy but still put together.
    I hope you can answer a question I have about ladies’ hats; why do they come in only one size? Men have, literally, about five hat sizes from which to choose, but ladies are One Size, Good Luck. We, too, have different size heads. Some of us have thick hair, some of us get migraines and can’t tolerate a tight hat band. As a rule, the best I can do is a men’s straw hat in the least masculine style available. I wish I could get a cute one like yours! 😩

  16. Jackie
    April 5, 2021 / 7:18 am

    I’d love to see some sun hats in XS/S. The one-size-fits-all business just doesn’t, and our scalps need protection, too.

    • Jennifer
      April 5, 2021 / 4:00 pm

      Are you meaning for smaller heads, or narrower brims?

  17. Kathy
    April 5, 2021 / 6:40 am

    Wow! Love this look on you, Jennifer, and I would love wearing it myself! Polka dots are so cheery. That outfit made me smile!

  18. Gail Ardiel
    April 5, 2021 / 6:31 am

    Soon as I look at the page my thoughts were Loving the look. You look fabulous. This is my style , Thanks for showing us how to dress, from Ontario.

  19. Barbara
    April 5, 2021 / 6:30 am

    What a great outfit for spring! I love both polka dots and bateau necklines, but mint green doesn’t do much for my skin tone so I wish this top came in other colors. As others have written, I’m forever on the outlook for nice fitting cool cotton t-shirts. Can you help us out with this quest?

  20. Sue H
    April 5, 2021 / 6:04 am

    Love, love, love. I am a huge fan of polka dots because they’re both classic and cheery! I wish I could wear a hat with confidence. I always feel like I’m wearing a costume when I wear a hat. Do others feel that way too?

  21. Rose
    April 5, 2021 / 5:56 am

    Fabulous outfit on you. I love polka dots and I really like those jeans. I am always looking for the perfect white t shirt that you cannot see through. My new quest. Thanks for all the ideas.

  22. Maribeth conklin
    April 5, 2021 / 4:59 am

    I like polka dots. The mint green is very pretty.

  23. Marie
    April 5, 2021 / 4:58 am

    Love the look of the mint green and light wash Jean’s.
    My quest each year is to find lightweight t shirts that are not see through, preferably v neck, in pretty colors. I find some of the pima cotton ones are too hot in the summer. I also avoid those with stretch, since they tend to cling.

    I love the sandals. Look comfortable, stylish, and with a heel, safe to walk in for my aging feet as well!

    Appreciate all the fashion ideas.

  24. Jan
    April 5, 2021 / 4:55 am

    From the top of your head to the tip of your toes, this look is a winner for me!!
    I would love to add each of your featured pieces to my wardrobe. How fun is that polka dot top! I am always looking for jeans with a higher cotton blend. They just feel so much better and this cut is my cup of tea. Your hat, sun glasses and sandals all compliment the whole look.
    It’s a youthful glow that so many of us could duplicate.
    What an awesome start to a new week! Happy spring ladies!

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