How to Wear Gingham in the Fall

How to Wear Gingham in the Fall Shirt, $140; Jeans, $178; Belt, $15; Shoes, $60; Bag, $16; Vest, $35

How to Wear Gingham in the Fall

We have had numerous requests for more posts featuring casual/weekend wear, so today we’re introducing Weekend Inspiration.  In these posts, you’ll find both product recommendations and inspiration to get you ready for various weekend activities.  As with all of our posts, not every look will be for everyone, but every look will keep to our aesthetic of updated classic style with the occasional twist. Today, we’re launching with a look that I live in this time of year. Of course, if you have specific questions or requests, just add them in the comments below!

I love a good button down. I know it’s tough if you have a larger bust, but for those of us who spent the better part of our adolescence wondering when we were going to fill out more than a training bra, button downs work well. For the weekend, look for something in a relaxed slim fit. A gingham pattern, like this one from Reese Witherspoon’s Draper James, is preppy perfection. If you layer it with a thin quilted vest, it will take you through the chilly part of Fall. (This one from Old Navy is a reader favorite.)

We talk a lot about the importance of layers and cohesiveness, and this outfit covers both. The quilted vest layered over the shirt and the belt adds some needed dimension and helps bring the fresh gingham pattern into the season. The addition of the belt (only $15) is important. If you tuck the shirt in the belt finishes the look. Then I got all matchy-matchy. I found a lovely pointed flat, because it’s still a little too warm for a boot in my neck of the woods.  And the bag? The bag is from Forever 21 and is only $16! I know, it’s crazy. Because the tan color shows up three ways (belt, shoes, bag), you create a strong cohesive element, and the look becomes grounded.

Wear your favorite straight your skinny jeans if you go for a pointed flat, as the season progresses, wear a riding boot. We’re showing a pair of DL 1961 jeans, my current weekend and travel favorite. If you eventually wear something like this with an ankle boot, you can wear a slightly bootcut jean, and your proportions will be one point.Shop This Post


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

  1. Could this button down be worn to work on a casual Friday layered under a sweater or blazer or is it too casual? As I prep for the 30 day style challenge I noticed a void of button down shirts in my wardrobe. I desperately need a white one and have always loved gingham but am torn spending $140 on a shirt I can only wear on the weekends. If it’s versatile I am more than willing to spend the money. You convinced me to invest in AG jeans and now I practically live in them. 🙂

    1. Hey Sam! You know, I went back and forth on this shirt because of price, but I decided because it had a range of sizes available I could at least show it for inspiration. I found this J. Crew option that’s $60, but I haven’t seen it in person. Either one you could totally wear under a blazer for work. Great way to get your money’s worth. And I’m so happy the AG jeans were a success. They are still one of my favorites.

  2. Megan,

    I love it! Everything about it! Thank you so much for this post. 60° and rainy is the forecast in ND for tomorrow morning’s 5th grade football game. This is just the inspiration I needed to be put together sideline Mom. I will be busting out the vest (and the boots since I’ll be outdoors for 2 hours).

    Thank you!

    1. Thank you! And I’m so jealous! My kids have a track meet this Sunday and it’s going to be 80! I’ll still be in shorts. I can’t wait for boot weather.

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  • Up on the blog today:
🍁How to Wear a Plaid Blazer to the Office.
A causal and cool look to update your work worthy denim.
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