Shifting Into Fall

Embracing fall clothes can be a challenge when the temperatures are still hovering in the 80s. I stored my most summery pieces last week because while they’re still comfy, they look totally out of place at the beginning of October. So what to wear? Plaid is a great option. It looks right for this time of year but flannel versions are out of the question. Luckily there are some great new lightweight versions that give a fall look without feeling hot.

Jennifer Connolly of A Well Styled Life wearing lightweight plaid

We met friends for dinner at their golf club Friday night and I wore this lightweight plaid shirt. I love the classic black and white pattern so I kept that theme throughout my entire outfit.

Jennifer Connolly of A Well Styled Life wearing lightweight plaid
wearing- shirt | pants | earrings | bracelet similar | shoes

Jennifer Connolly of A Well Styled Life wearing lightweight plaidI wore my favorite Eileen Fisher Jennifer Connolly of A Well Styled Life wearing lightweight plaidI also painted my toenails red which is a sure sign of fall to me. I wore simple silver jewelry and my poofy pin.

I found this shirt during my first trip into Zara last week. It has an asymmetrical hemline and a black sash that I plan to use on other things. They don’t carry investment pieces but their prices can’t be beaten.

Lightweight plaid is a great transition pattern and there is lots of it available. This is my first plaid anything and I’m really enjoying it.

I spotted this one in Talbots last week and thought the ruffled collar was a nice touch. This tunic from Foxcroft is totally classic and light. This one is pricey but oh so unique. Loft has some feminine looking ones here and here.

How do you transition into new seasons?

Thanks for reading and have a great day!


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  1. Curious Jennifer the size of your blouse.

    1. I bought the small. It’s pretty loose so the medium swam on me.

  2. Love your plaid shirt. I have never shopped Zara and thought I would check it out. I found a floral blouse I really like and tried to order it, but when I tried to enter my information, I couldn’t figure out how to enter a “valid” phone number. I thought my phone number is “valid”. Any suggestions?

    1. I haven’t tried to order online yet. Do they have a customer service number? I’d start there.

  3. I use vests to transition. Many are lightweight & can be removed if it becomes too hot. Over the years I’ve collected a variety of weights, colors & fabrics. They can be dressed up with a belt underneath or a scarf. And, of course, the Jean jacket – my go-to for transition.

    1. A vest is a great transition piece, Katrina. I only have heavy ones so I need to keep my eye out for lightweight ones.

  4. That’s a great looking outfit. The top is so versatile. I like how you mix styles from classic to slightly edgy. I would love those shoes but not sure I can comfortably wear the heel. It looks great on you though! It’s still hot here in Florida and looking forward to wearing Fallish outfits.

    1. It really is versatile. I’ll get a lot of wear out of it this fall. We’re anxious for it to cool off too! This summer is never-ending.

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