My family goes apple picking every year.

We leave our respective homes in the tri-state area and make the trek into the country to enjoy the fall. We eat old-fashioned donuts, sip hot apple cider, and steal each other’s pickles-on-a-stick. It’s one of my favorite traditions and as my nieces and nephews have started to get older, it’s become a lot more fun.

Last year we made the mistake of waiting until the end of October to meet up and found that all our favorite apples had been plucked from the trees! Never ones to be beat, we set our calendars for the Honeycrisp harvest and planned to get our picking in early. That meant, instead of the knit hat and gloves I donned last year, I could wear something a little less bundled.

This black and beige gingham a-line from Anthropologie (similar here) was the perfect choice for the early fall weather. It’s one of those long-sleeved dresses that sits in your closet waiting for the exact right temperature to wear it: not too hot so your arms overheat, but not too cold that your legs freeze. You want one of the few, crisp, fall days that is truly comfortable.

In the morning when the air was cool, I added a simple down vest. As the day warmed, I took it off and rolled up my plaid sleeves, ready to start picking.

White fluffy clouds in the sky, bees humming, and ripe apples made for a very happy day.

I love a good Fuji, but….

…Honeycrisps have my heart!

I’m always looking for dresses that are easy to throw on and don’t need a lot of accessories to dress up. While I don’t wear plaid very often, the pattern of this dress made me think of brush strokes and is less regular than a traditional gingham. It felt perfect for fall.

The orchard rows are usually muddy and lined with apple remnants, and since it had rained a few days before, I thought it best to wear my black Hunter Wellington boots. Maybe it’s because I didn’t have rain boots as a kid, but I always look for a reason to wear my wellies. The rubber shoes make me think of big muddy English estates and fall foraging – not to mention the sheer joy of splashing a rain puddle knowing your feet wont get wet.

The wellies did a good job of offsetting the feminine shape and length to the dress, adding a little ruggedness to the look.

I also like to use the Wellington boot socks to keep my feet cozy and prevent blisters (that rubber rubs!).

I’m looking forward to the next few weeks full of trips to the city, butternut squash recipes, and cool nights drinking hot tea under my furry blanket. I’ll try to capture these autumn moments and get a few more wears out of this dress before it goes back into the closet, awaiting the next perfect fall day!

P.S. To those of you in the path of Hurricane Matthew, I hope you stay safe. <3