Today I am continuing my series on styling denim jackets. Some of you commented that you did not think you could wear a jean jacket and that you had given up trying. I hope that after reading my last post, you have started to rethink that.

Here is what I am picturing what you look like when you try on a jacket:

If you look at all like me in this photo, you take your jacket and run to Goodwill. There is nothing at all flattering about this look! But wait! I want you to learn to try things and experiment a little. With just a little tweaking, this outfit turns into this:

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I had already followed two of the rules when I purchased the jacket:

  • Not baggy
  • Right proportions

I followed up by applying the other two rules:

  • Roll up the sleeves
  • Don’t button

I then added some accessories, a belt to give me a fake waist, and some cute boots. Good to go!

The other point I want to make in this post is that you can wear denim on denim, but it looks much better if you pair light with dark. As you can see in the middle picture, it is too much to have the same shade of denim on top and bottom.

Hope you are learning along with me. More to come.


Hello friends,

Several of you have mentioned that you find styling a denim jacket challenging, and are to the point where you don’t think you can wear one. I thought I would research that a little, and try some experiments of my own.

Since I am a visual learner, I looked at a lot of pictures of women of all sizes in denim jackets, and although I might not be the best at analyzing, I did notice a few things. First of all, denim jackets for the most part are by nature boxy. And boxy is not what we want ladies! It is not even a good look for small young people:


I did however, see a lot of people who looked really great in a denim jacket:


Now the first thing I noticed about the difference was that the second set of photos had the sleeves rolled up. Bingo! Rule #1 for styling your jacket:


I decided to try this for myself:


Hmm. I think I’m on to something.

I also saw a lot of pictures of people who were wearing baggy jackets that looked awful:


So rule # 2 must be:


The next thing I noticed was that buttoning the jacket was not a good look:


I could not find one single photo of a jacket that looked good when it was buttoned, so here is rule # 3:


After looking at so many photos, the biggest thing just seemed to be getting the proportions right. The jacket should not be too big/baggy. It should not be too long or too short. The bottom should hit you at a flattering place.

You might have to try on several jackets to find one that is flattering.

 BAD        GOOD

See what I mean?  The most flattering look seems to be a jacket that comes to your waist level or just a bit below.  So—


To recap:

  • Roll up the sleeves
  • No baggy jackets
  • Never button
  • Wear the right proportions…bottom should be around waist level

If you don’t have a jacket, here are some links to get you started looking. By the way, the one I am wearing was $19.99, so don’t think you have to spend a fortune to find a good one; in fact, I would start at Goodwill. I bet there are lots of them there. I know I have sent more than one to the Goodwill racks. 😉

Here are a few I found on Amazon. (Disclaimer: if you click and purchase, I will receive a small commission)

Womens Basic Button Down Denim Jean Jacket (Medium, MediumBlue)


Lee Women’s Modern Series Holden Denim Jacket, Gauntlet, Medium


URBAN K WOMENS Long-Sleeve Button Up Denim Jean Jacket (S-3XL)


Riders by Lee Indigo Women’s Denim Jacket, Drenched, M


I think I have convinced myself that anyone can wear a denim jacket, but it might take a little work to figure out your best look. Set aside some time and try on several jackets to see what flatters you. Use the four “rules” I mentioned. If you can’t find stores with good selections, order several online and return the ones that don’t work.

Seems like a lot of effort, but I think it is worth it, because a jean jacket is a very versatile wardrobe staple that has been around for decades and is not going anywhere.

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I would love to hear from you if you have any success finding and/or styling a jean jacket. I hope I have encouraged you to do so. If I haven’t yet, stay tuned, because I have been trying on lots of things with my jacket and will show the good, the bad, and the ugly, as usual.  This will definitely be a series!

If  you would like to see pictures of most of the outfits I have put together, click on the page for the category you would like to see. On a mobile device, click menu to access the pages. You can also follow me on Instagram@over50under20.