Five Ways to Style a Sweater and Jeans

Happy New Year and welcome to 2019! I have some posts planned based on your requests and BTW…you can always suggest a topic you’d like me to cover. Simple classic pieces often make up the backbone of a wardrobe. They make getting dressed easy but they need some help to avoid looking plain.

Several of you asked me to style things already in my closet, in multiple ways, so today I’m styling a v-neck sweater and black jeans in 5 different ways.

I started with tiny silver earrings, ballet flats, and my watch. This look is classic but borders on boring for me. I would hang around the house in this but if I was going out I’d change it up with accessories.

how to style a v-neck sweater and straight jeans 5 ways

v-neck sweaterblack jeansleopard booties (similar) – earrings (similarscarf (similar)bracelet similar

I switched to larger hoop earrings and a bold cuff bracelet. This draws the eye up to my face and bounces it back mid body. Then I added a textured cowl scarf and leopard booties. The texture of the scarf is a good balance for the pattern on the booties.

For a more streamlined look, I switched to black booties which creates a longer leg line. Then I topped it with a fringed black ruana, a statement pearl necklace, and small pearl earrings. A dressier look but still casual because it’s jeans.

styling a sweater and jeans with denim jacket a neck scarf

denim jacketsweater jeanssneakersscarf (similar)

Dressing it back down, I swapped the booties for leather sneakers and added my new favorite denim jacket. Athletic sneakers for the gym wouldn’t achieve this same look. I tucked a small silk scarf into the sweater neckline for color and added dangling, artsy earrings.

Jennifer Connolly of A Well Styled Life showing 5 ways to style v-neck sweater and black jeans

sweater jeansblouse (similar)booties (similar) – necklace (similar)

Here I wore a thin white shirt under the sweater and changed to comfy booties in a similar color to the sweater. Notice how this makes my legs look shorter than the black booties. The heel heights are similar so it’s the color that makes the difference. I added a sparkly necklace and small earrings.

Accessories are the magic here which allows you to create multiple looks from the same classic pieces.

Do you mix things up or wear them the same way each time.


Thanks for reading and have a great day.


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


  1. Joyce
    January 3, 2019 / 5:03 pm

    Really enjoy your practical inspiration on using our existing wardrobe and accessories. My question is how do you keep your black jeans nice and black? I’m very careful to use cold water turning them inside out with minimal detergent but alas they fade and I have to purchase new ones. Have any tricks?
    Have a Blessed New Year Jennifer.

  2. Jo
    January 3, 2019 / 5:16 am


    What is the brand/name of the black boots pls?

    The link goes to Soft Surroundings – error msg.

    • January 3, 2019 / 7:28 am

      I’m sorry they seem sold out. They are the Seychelles Wake up bootie

  3. Donna
    January 2, 2019 / 10:59 pm

    Ahhh! The pictures worth a thousand words! Can’t wait to take another look at the gems I already own. Also, you do a great job of demonstrating lots of looks within the smart casual category, which is where most of my life falls. Kudos for showing what variety can come from small changes. Thanks!

    • January 3, 2019 / 7:29 am

      So glad you enjoyed Karen. That’s the category I live in too:)

  4. January 2, 2019 / 6:30 pm

    Definitely one of your best posts! It feels like you were in my closet! And you just pulled me out of a rut!

    Q: How do you know when it’s time to give up on an outfit or a piece? Example: I had grey jeans I wore a gazillion times, styled many ways. After 2 years I finally began to worry if I was done with them. Should I replace them or had I worn them too long? Should I still buy a new accessory for these old jeans to find another new look? Should I reinvent or am I done with them? How do you know?

    • January 2, 2019 / 6:59 pm

      Here’s the way I would approach it-
      Do they still fit well?
      Are they worn out?
      Do they make me feel stylish?
      Are they an inherent shape and color for me?
      Also…I do not buy accessories for a single purpose or outfit. I buy what I find unique and love.

  5. Eileen
    January 2, 2019 / 2:41 pm

    Thanks Jennifer. This post was perfect. I have such a a hard time with dressing now that I am retired. I go out to classes and volunteer work and feel that I always look the same. You have given me great ideas. Tomorrow I will pull out a scarf and some jewelry and Jazz things up.
    Wishing you a happy and healthy new year. And mor columns like this please.

    • January 2, 2019 / 6:51 pm

      Happy New Year Eileen!

  6. January 2, 2019 / 2:18 pm

    Such a helpful post, Jennifer. Thanks for the inspiration!

  7. Joanna
    January 2, 2019 / 2:13 pm

    Simple changes made such a difference in the feel of the outfit ( grey sweater/ black jeans ). I really noticed the difference in your perceived leg length from the black booties (taller) to the others. Do more of these please!

    • January 2, 2019 / 6:48 pm

      I will do more of these. So glad you liked it

  8. Joanne
    January 2, 2019 / 12:27 pm

    What a wonderful post! Jennifer, please do more of these, it was most helpful. Thanks!

    • January 2, 2019 / 6:47 pm

      I will do more like this and thanks for being here Joanne

  9. Cyndi
    January 2, 2019 / 12:23 pm

    Great post! I really enjoy these where you show us different ways to style some basic pieces…so helpful to have ideas how to make better use of pieces we already have in our closets. Thanks!!!

  10. Connie
    January 2, 2019 / 9:56 am

    Fabulous post Jennifer! I love how you put everything together, especially the necklace with the blouse and sweater. This morning I pulled out a navy sweater and red wrap I haven’t worn in ages to go with new pin stripe pants. This is just the kind of casual dressing my retirement and chasing grandkids needed!

    • January 2, 2019 / 6:46 pm

      I’m so glad you liked it. That sounds like a wonderful combo Connie!

  11. Allison
    January 2, 2019 / 9:17 am

    Hi Jennifer, this is a fantastic post but I have a little peeve about all the advertising showing up on your blog. It makes reading the relevant text in context with the photo a pain in the derrière because the ads pop up between the photo and the text. I read your blog on my iPad so I have to scroll up and down or constantly be x’ing the ads. Also scrolling ads on the bottom are very distracting. I get that it’s a way to make some money but I read a lot of blogs and have been unsubscribing from the blogs that push the ads. Your ‘s I really like and don’t want to unsubscribe but….is there anything you can do about this?

    • January 2, 2019 / 6:41 pm

      Hi Alison. I’m sorry to hear the ads offend you. I have reduced the number of “in post” ads but I do need them to help cover the costs of maintaining my blog. Thanks for your patience.

  12. Kathleen O'Brien
    January 2, 2019 / 9:13 am

    I love idea of being able to shop in my closet, but making it unique and different. Thanks for this great post. Give me ideas to see my things a little differently and create some new looks with what I already have!

  13. Suz
    January 2, 2019 / 9:03 am

    I agree with all of you! These outfits match my personality, budget and retired lifestyle. I always love a shawl artfully draped over the shoulders, but can never make it “stick” (your first pic). Any helpful hints for that?
    And one more quick question – do you cut or unsew the tag on your scarves? Mine always seem to be peaking out .
    Thanks for posting, Suz from Vancouver

    • January 2, 2019 / 6:17 pm

      I use a seam ripper and remove them. I also remove tags in blouses and sweaters if they rub or show through. In a shawl, I like to wrap the side that crosses under the side that hangs down. That stays in place better.

  14. Sandra Matthews
    January 2, 2019 / 8:49 am

    Hi Jennifer, Really helpful and interesting ideas. I am about your height and shape (broad shoulders, narrower hips) and weight, and loved the visual on the black boots versus flats or different coloured boots as far as leg length goes.

    Thanks, always enjoy your posts,


    • January 2, 2019 / 6:11 pm

      I’m so glad you liked it Sandra

  15. Evelyn
    January 2, 2019 / 8:29 am

    So so helpful. Just what I needed.

  16. Susan
    January 2, 2019 / 7:36 am

    Great post. Here’s a question- what do you do about socks in the winter? There’s no way, where I live, that I can go bare legged in January! Can you show the same looks with socks or hosiery? I see all these great looks in blogs but no one is ever concerned about freezing water in their shoes! Or glaringly white ankles that have lost their tan! And really, wearing old shoes then changing in the car you still have the same issues…
    Anyone have some real suggestions?

    • Susie
      January 2, 2019 / 9:20 am

      Hi, my feet are always cold so I wear Smartwool socks that match the color of my pants. They are thin but also warm so they work in all my boots and shoes and under my skinny jeans. I try to wear pants that are long enough to reach my shoes. It is very wet where I live so I also give all my foot wear a coating of Never Wet that I get in the paint department at Home Depot.

      • January 2, 2019 / 6:10 pm

        Brilliant Susie, thanks for sharing!

      • Susan
        January 3, 2019 / 3:55 pm

        Thanks, Susie!

  17. Annette
    January 2, 2019 / 7:02 am

    Absolutely love your ideas. With a few suggestions from you, I went straight to my closet & started planning outfits. Thank you so much for helping me realize what I could do too.

    • January 2, 2019 / 6:07 pm

      Awesome Annette. I’m so happy to hear that

    • Tamara
      January 13, 2019 / 8:34 pm

      A stylish girl I knew in college kept combinations of her clothing on index cards. On any given day she could pull a card out and it would list shoes to hat and everything in between. There were hundreds of cards (her family owned a boutique in Manhattan) and I poo-pooed the idea but as I get older and sometimes forget what’s in my closet, this would be awesome.

      • January 14, 2019 / 4:22 am

        That’s a clever idea.

  18. Betty West
    January 2, 2019 / 7:00 am

    Great post. I also fall into wearing the same way! Love the way you showed how to use accessories

  19. January 2, 2019 / 6:57 am

    Great post on how to change things up. I’m trying to concentrate on building basics which can be accessorized.

  20. Ann
    January 2, 2019 / 6:03 am

    Happy New Year Jennifer!
    I noticed the grey booties are very low cut on the sides. What kind of sock liner do you use with that bootie?

  21. Kathleen
    January 2, 2019 / 5:54 am

    Ditto. Thanks for showing us how to shop our closet and create great outfits. It’s so easy to get in the habit of throwing on the same clothes with no attention to detail. Even easier to take it up a notch!

  22. BethW
    January 2, 2019 / 5:53 am

    Loved this post. Ideas about how to wear clothes different ways is very helpful. It was also helpful to see how the different looks changed how you looked such as longer legs with the black boots.

  23. Julia
    January 2, 2019 / 5:49 am

    I agree with all of you! This style of dress matches my budget and retired lifestyle. Now I just have to beef up on my accessories! Thanks, Jennifer

    • January 2, 2019 / 6:02 pm

      Accessories make all the difference in my wardrobe. Happy New year

  24. Ramona Puckett
    January 2, 2019 / 5:41 am

    Love this! I agree with Sondra, I usually shop my closet but it’s nice to go out and see what’s out there and add to whatever I have! Thank you for your posts, they are really helpful and I learn a lot!

    • January 2, 2019 / 1:25 pm

      Happy New Year Ramona!

  25. Sondra
    January 2, 2019 / 4:48 am

    Love this, Jennifer! For me personally, this is the type of post I love most. We can’t all go out and buy new clothes every day and with some of us on fixed incomes, that’s not possible. Thank you for showing us all of the ways to wear just two simple pieces that most of us already have in our closet.

    • Roxanne
      January 2, 2019 / 5:40 am

      Sondra, I couldn’t have said it better! More ideas like this post would be great!!

    • Memee
      January 2, 2019 / 5:42 am

      I totally agree with Sondra. Thanks for a great post.

    • January 2, 2019 / 1:24 pm

      I’m so happy you liked it ladies! Happy New Year.

  26. Carolyn
    January 2, 2019 / 4:38 am

    Great post. This is why I follow you, you teach, not many do! Keep us current.

    • January 2, 2019 / 1:23 pm

      Thanks Carolyn. Happy New Years!

  27. Beth M.
    January 2, 2019 / 4:30 am

    Great looks! Which was your personal favorite?

    • January 2, 2019 / 1:23 pm

      That’s a tough one because I’d wear them all for different occasions. I think the one with the leopard booties.

  28. January 2, 2019 / 4:24 am

    I loved today’s discussion. Not only for the accessory ideas, but also the net result: more casual, longer looking legs, etc. thank you. Happy New Year!

    • January 2, 2019 / 1:21 pm

      I’m so glad you liked it. Happy New Year Paulette!

  29. Shari
    January 2, 2019 / 4:10 am

    Jennifer! One of your best columns ever! This is the way I dress most of the time. Even our church is dressy casual so I loved the dressier look yet with jeans!
    This was so fun and good for our outlook…just don’t go our looking so dowdy when you can spruce it up!

    • January 2, 2019 / 1:20 pm

      Accessories make all the difference. Happy New Year Shari!

  30. Yvonne
    January 2, 2019 / 4:05 am

    Great post and a great reminder to change up our basics with different accessories. I quite often fall into the habit of always wearing something the same way.
    Happy New Year Jennifer!

    • January 2, 2019 / 1:19 pm

      Happy New Year Vyonne!

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