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Plaid and Pearls

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

wearing pearl cuff jeans from Ann Taylor
PLAID SHIRT / PEARLIZED JEANS on sale / BOOTS similar / BRACELET / EARRINGS / SUNGLASSES similar / LIPSTICK in FIG

 

 

Jennifer Connolly modeling Hunter Rails plaid shirt

Iā€™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. Check out How to Wear Booties and How Long Your Pants Should Be.

Jennifer Connolly of A Well Styled Life wearing plaid and pearls

These jeans are narrow at the ankle and have a pearlĀ detail that would be a shame toĀ 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.

Hunter Rails plaid shirt from Nordstrom
PLAID SHIRT / PEARLIZED JEANS on sale / BOOTS similar / BRACELET / EARRINGS / SUNGLASSES similar / LIPSTICK in FIG

Plaids come in every color of the rainbow these daysĀ 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. TryĀ to match the plaid proportion to your proportion.

Style expert Jennifer Connolly of A Well Styled Life styling plaid with peals
PLAID SHIRT / BRACELET /Ā EARRINGS / SUNGLASSES similar / LIPSTICK in FIG

As with all button downs, beware of buttonhole gaping. Itā€™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.

SHOP THE LOOK

Are you a fan of plaid?

Thanks for reading ladies and have a great day!

 

 

14 Comments

  1. Love this look. So casual yet put together!

  2. Paulette Levy says:

    Wow! A cute look! I don’t own any plaid except my Talbots Buffalo red/black puffy vest with fur collar (faux). I may look into a shirt…..
    I wear lots of dark wash denim, but usually pair with something a little classic like white tee and a blazer or a turtleneck on a cold windy day.
    On the booties I do win two pair…both black. I love them but do watch my pant hem when I wear them. Thanks for reminding all of us…..

  3. Dolly Bersalona says:

    I love your style?

  4. 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.

    1. Cool temps call for plenty more of those ā€œI just want to be comfyā€ days.

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

  6. 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!

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

  8. 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.

  9. 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?

  10. 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.

  11. Sheila in Garden City, SC says:

    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!

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