4 Fall Festival Fashion Outfit Ideas for Women Over 40

Last Updated on December 29, 2017 by Ellen Christian

Have you been wondering about fall festival fashion? I love attending fall festivals each year. There are so many great ones in the area to enjoy. After all, what isn’t there to like about pumpkins, hayrides, corn mazes, and apple cider? When I’m planning my weekend out, I always wonder what I should wear. I want to be comfortable but not too casual. This giveaway is a partnership with Nakturnal.

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4 Fall Festival Fashion Outfit Ideas for Women Over 40

Fall Festival Fashion

So, what exactly do I wear to a fall festival so that I am both comfortable and stylish? Of course, much will depend on the weather in your area. Here in Vermont, it’s rather cool and damp in the fall. So, if you’re heading to New England or someplace like the Kings Island Great Pumpkin Fest, you’ll want to dress in layers.

5 Fall Festival Fashion Outfit Ideas for Women Over 40

Oversized Sweater

I’m a huge fan of oversized sweaters because they hide my hips. OK, so maybe this isn’t an issue for you. But, oversized sweaters are also warm comfortable and easy to layer. You can dress it up or down with jewelry, boots, or a scarf depending on which type of festival you’ll be attending.

5 Fall Festival Fashion Outfit Ideas for Women Over 40

Flannel Shirts

Here in the country, flannel is very popular in the cooler months. You can wear it as a short or a jacket depending on how cold it is. You can also wear a plain white shirt under it or an oversized sweater over it to layer for changing temperatures. Roll the sleeves up or down. Tie it at the waist or tuck it in. It’s all up to you.

5 Fall Festival Fashion Outfit Ideas for Women Over 40


It wouldn’t be fall without my favorite pair of boots. The style you choose depends on your preferences, but please consider the terrain and the weather when choosing. You don’t want to find yourself walking through a hay field in the rain in a pair of boots with 4″ heels. Consider cowboy boots or leather boots with a more modest heel if you’ll be walking in rural areas.

5 Fall Festival Fashion Outfit Ideas for Women Over 40

Weather Tips

Remember to dress for the weather in your area. It’s still possible to get a sunburn if you’ll be out in the sun all day. Pack your favorite hat and sunglasses when considering your outfit. You get bonus points if you wear a cowboy hat!

One of my readers will win a $25 Kohl’s gift card to use toward an outfit to wear to the fall festival of their choice.

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109 thoughts on “4 Fall Festival Fashion Outfit Ideas for Women Over 40”

  1. I love corduroy for the Fall and despite the 90 degree temps this week here still, have been wearing my fave hunter green lightweight corduroy pants. They just hit below the knee so I’d love to wear them with cowboy boots as you described. I’d also love to get a rich chocolate brown corduroy pant with pretty brown boots and I’d pair it with a colored denim jacket. I think that would make a great outfit for outings. I have lots of cowboy hats too! Can’t wait for cooler weather!

  2. Id love to wear a dress with a nice sweater over top, I just love autumn and being able to dress up or down and layer!

  3. I would wear a pair of comfy jeans and a oversized sweater with a t-shirt underneath in case I got too warm. Thanks for the chance to win.

  4. I’d wear my plaid flannel jacket, a warm sweater, boots with a flat heel so I can walk long and far, my winter jeans if I can get my chubby rear into them and sunscreen and a hat!

  5. I would wear the really cute oversized sweater you mentioned with a comfy pair of skinny jeans and some black riding boots!

  6. Oh I would love to wear that oversized sweater with jeans and boots! That sweater looks so comfortable. I love those for fall and cooler temps!

  7. I would wear my burgundy moto jeggings with my black boots and soft black sweater with a tank underneath in case I get too warm.

  8. I would layer with a short sleeved t-shirt under a soft flannel shirt. I would also wear comfortable jeans and my favorite boots.

  9. I would wear a comfy pair of jeans, a sweater, and some nicely stitched boots to the Kings Island Great Pumpkin Fest.

  10. I would wear a pair of yoga pants, a sweater, or flannel and pair of tennis shoes. I’m all about comfort!

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