Plaid and Pearls

Plaid and Pearls
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Nothing says casual quite like a soft plaid shirt, flat booties, and comfy jeans. Add some unexpected pearls to the mix and you have my version of cowgirl dressing.



Jennifer Connolly modeling Hunter Rails plaid shirt

I’m not tucking many things in after my recent holiday so tying this shirt at my waist is just what the doctor ordered for shaping and to shorten its proportion.Exploring downton Loomis CA in Hunter Rails plaid from Nordstrom

Did you ever wonder what length pants to wear with booties? The answer depends on the width and length of the pant leg combined with the height of the bootie shaft.

Jennifer Connolly of A Well Styled Life wearing plaid and pearls

These jeans are narrow at the ankle and have a pearl detail that would be a shame to cover so these short ankle booties work best. Longer skinnies would look strange with this bootie because they’d wrinkle at the boot edge, never stay tucked in and would need to be folded up.

Plaids come in every color of the rainbow these days so look for ones that flatter your complexion. Large plaids look best on tall or larger women but small plaids can lose their impact if they get tiny enough to resemble gingham. Try to match the plaid proportion to your proportion.

As with all button downs, beware of buttonhole gaping. It’s best if there is a button closure that is level with the widest part of your bustline.styling plaid and pearls in Loomis CA

A necklace would have felt too fussy with this look so I stuck with simple hoop earrings and my favorite chain bracelet.


Are you a fan of plaid?

Thanks for reading ladies and have a great day!



Affiliate links within this post may generate income for AWSL.


  1. Sheila in Garden City, SC
    November 6, 2018 / 4:28 am

    Jennifer, such a good look that works well for our casual lifestyle. I have several bracelets from that designer and love the look (and the clasp is effortless). I wear a single strand of pearls often, Ralph Lauren look!

  2. November 6, 2018 / 5:24 am

    Jennifer, I really love reading your hints, i.e., leg proportions in jeans/pants when worn with booties. So helpful!! Also, your size and proportions are very similar to mine, so it’s easy to see which of your styles would work for me. I’m really loving your site.

  3. November 6, 2018 / 6:05 am

    Hi Jennifer, I love this casual look. I bought these jeans too after seeing them in one of your posts and I love them. I am curious about the purse. What can you tell us about it?

  4. November 6, 2018 / 6:24 am

    This is a darling look & I’m in the market for new dark wash jeans, these are perfect! I love the idea of tying instead of tucking your shirts in front. Those after vacation extra lbs are so annoying – after our 3 week road trip I was shocked to get on the scale.

  5. Joanna
    November 6, 2018 / 7:35 am

    Love those jeans! They are the perfect length for booties, too. I’m not a plaid shirt kind of girl but it is a cute, casual look on you.

  6. Mo
    November 6, 2018 / 7:36 am

    Love these booties!

  7. Janet
    November 6, 2018 / 1:10 pm

    This look is very flattering on you. Coincidentally I just bought some booties and have no idea what pants to wear them with. Any style hints would be greatly appreciated!

  8. November 7, 2018 / 12:08 pm

    Love the plaid Jennifer! I need to get something like this for our tree cutting/family photo event coming up. Thanks for the inspiration!

  9. Lily
    November 8, 2018 / 8:21 am

    I am a fan of plaid – sort of. I am typing this comment wearing my favorite Uniqlo plaid flannel shirt. I love it because it is such a pretty muted pink, warm, comfy fit, washes beautifully. It’s also 100% cotton and only $30! All that said, it’s not dressy at all. Only for blah days when you just want to be comfy.

    • Jennifer
      November 8, 2018 / 11:40 am

      Cool temps call for plenty more of those “I just want to be comfy” days.

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