4 Fall Festival Fashion Outfit Ideas for Women Over 40

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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.

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.

a Rafflecopter giveaway


  1. Jill Jeffrey says

    I’d wear an oversized sweater for comfort and a pair of boots!

  2. ellie sheely says

    warm sweater, leggings and comfortable shoes, like a hike boot

  3. 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!

  4. Liz Newsome says

    Sweater dress, leggings, boots, and a fun scarf!

  5. amy stonger says

    I’d definitely wear an oversized sweater with some knee high boots and a sweater.

  6. I would wear something warm.

  7. Dan Dykstra says

    My wife and I would dress in layers for the changing weather. I would wear my cowboy boots.

  8. I would wear skinny jeans, a cardigan and knee high boots.

  9. This is a great list of classic fall outfits!

  10. Noelle Carroll says

    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!

  11. Oversized sweaters are my favorite! They’re so comfy, especially paired with a chunky scarf!

  12. I’d wear warm sweater,leggings and scarf.

  13. A sweater cardigan ,tshirt,jeans and boots

  14. Julie Waldron says

    I’d wear a casual sweater & jeans.

  15. 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.

  16. Jessica Beard says

    I would wear jeans and a comfortable sweater or sweatshirt.

  17. I would wear skinny jeans, boots and a long sweater

  18. I would wear skinny jeans with knee boots and a comfy sweater.ย 

  19. 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!

  20. I love those cowboy boots in the first photo and would love to design an outfit around something like that!

  21. amanda whitley says

    i would wear my dark skinny jeans and brown boots and a loose sweater.

  22. crystle tellerday says

    my new bat leggings and a shirt

  23. Leggings & a tunic! With some kicky ankle boots.

  24. Lindsay Hess says

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

  25. Margaret S Porter says

    Cute sweater, skinny jeans and my new boots

  26. A cardigan, a logo tee, jeans and shoes.

  27. Some cute jeggings with a plaid flannel shirt, cute furry vest and boots!

  28. Rachelle Anderson says

    Comfy sweater, jeans, and boots

  29. Dana Rodriguez says

    I think I would wear a cozy sweater and my favorite boots!

  30. I would wear some comfy jeans and super soft flannel shirt.

  31. comfy jeans, a shirt and a jacket with some boots.

  32. I would wear a sweater, beanie, jeans, and boots. I don’t like to be cold in Fall weather.

  33. Skinny jeans, boots, and a sweater

  34. I would wear a flannel shirt under an oversized sweater along with skiing jeans and boots.

  35. Kimberly O says

    I love being comfy so I would wear leggings, a tunic sweater and boots. Thanks!

  36. Nancy Bowers says

    Iโ€™d wear jeans and a sweater with boots.

  37. sherry fowler says

    a sweater, jeans and comfy sketcher shoes for all of the walking that I will be doing

  38. angela smith says

    Leggings, boots and a sweater

  39. Juanita May says

    Jeans boots and my favorite flannel over a tee.

  40. my favorite cozy sweater and best jeans

  41. Button down flannel, jeans and boots!

  42. Allyson Tice says

    jeggings and a comfy oversized sweater!! oh then i would wear my brown boots!

  43. Eileen Boyce says

    Tunic, black pants and boots. ย thanks

  44. I’d wear a tunic with skinny jeans, and a cardigan if needed as well.

  45. Leah Shumack says

    Jeans, boots and an oversized sweater is my go to outfit for fall!

  46. amy guillaume linderman says

    my fave cowboy boots, my new jeans and my fave light blue sweater

  47. Stephanie Phelps says

    I would wear jeans with boots and a nice tunic!

  48. Katie Bellamy says

    I’m a jeans and Tshirt girl, but they’d be cute! ๐Ÿ™‚

  49. 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!

  50. I would wear leggings with a tunic, boots and oversized scarf! My favorite fall uniform!

  51. Annmarie W. says

    I would wear jeans, booties, flannel shirt and a denim jacket over that! Comfort is key!ย 

  52. I’d wear a swing dress, a long boyfriend cardigan, and comfy boots


  53. black leggings and a long tunic with flats

  54. I would wear a pair of skinny jeans, my tall, brown boots and a white t-shirt with a brown cardigan.

  55. I would wear a pair of boots with jeans and a sweater

  56. Lissa Crane says

    I would wear an oversized cable knit sweater, a pair of my favorite comfy jeans, and a pair of boots!

  57. I would wear a tunic, jeans and boots.

  58. Brandi Dawn says

    I would wear my favorite flannel and my big brown boots!

  59. Kayla Bennett says

    I’d wear a chunky sweater, leggings, and over the knee boots! (:

  60. Leggings, sweater and comfortable shoes.

  61. jeremy mclaughlin says

    Would buy my wife some boots.

  62. I’d wear leggings and an oversized sweater.

  63. I would wear a cable sweater and jeans.

  64. courtney hennagir says

    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.

  65. I would wear jeans, a tshirt with hoodie over it in case i get warm, and converse tennis shoes

  66. Breanna Pollard says


  67. I’d wear a warm cozy sweater, jeans and cute boots!

  68. Mary Gardner says

    I’d wear jeans and a loose sweater with some comfortable low heeled boots.

  69. angie depue says

    I would wear leggings, sweater and cute boots!

  70. I’d wear black jeans and a orange and black flannel shirt.


  72. rochelle johnson says

    I would wear boots, jeans, and a tank top covered by on open long sleeve shirt

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

  74. Joanna Peter says

    I’d wear plaid flannel, jeans, and ankle boots.

  75. Danielle Porter says

    leggings, boots, plaid shirt. ๐Ÿ™‚

  76. Jessica To says

    I would wear my favorite jeans along with comfortable boots. I’d top it off with a soft sweater.

  77. Heaven Kelough says

    I would wear a sweater, some jeans or leggings, and some boots! ๐Ÿ™‚

  78. Shea Balentine says

    Jeans, cozy sweater and sneakers! All about comfort!

  79. Marcia Goss says

    Jeans, white t shirt, cardigan, and boots.

  80. Angelica Dimeo says

    I would wear some leggings with a sweater

  81. Kelly Skibbe says

    I would wear jeans, a nice sweatshirt and my chucks!

  82. Audrey Stewart says

    Jeans and white blouse and my leather biker style jacket .

  83. I would wear a light sweater and jeans! I would have a fall colored sweater.

  84. Jeans and the leather biker style jacket

  85. If I went to the festival, I’d wear jeans, a flannel shirt, a sweater, and loafers.

  86. I would wear a utility jacket, flannel shirt, jeans, and boots.

  87. elizabeth miller says

    I would wear jeans, a white shirt, a long open sweater, and boots.

  88. I’d wear jeans and a comfy sweater.
    Thank you!

  89. A comfy sweater and my most comfortable boots

  90. I’d wear comfy clothes and a light jacket so I can layer as necessary.

  91. Lisa Queen says

    I would wear leggings and tunic. It’s still warm here so probably some sandals. Thanks!

  92. I would wear a pair of jeans, shirt and a sweater.

  93. Kat Emerick says

    Jeans, sweater and boots

  94. I would probably wear a black t-shirt and black pants to the Kings Island Great Pumpkin Fest!

  95. Mary Cloud says

    A long sweater over some tights with a great pair of boots

  96. Ellie Wright says

    I would wear jeans with a tunic and knee high boots.

  97. Jerry Marquardt says

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

  98. DeAnna Keller says

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

  99. Sarah Hayes says

    Id wear a cardigan and leggings with boots

  100. I’d wear the same thing I wear at Halloween when I throw on an orange shirt and call myself the Great Pumpkin.

  101. I’d wear jeans, over-sized sweater and boots!

  102. Seyma Shabbir says

    I get chilly so I would pick the jeans, boots and a wrap.

  103. Jennifer Marie says

    I would wear jeans, a warm sweater, and boots!

  104. Marisela Zuniga says

    leggings, a sweatshirt, and boots!

  105. I would wear a warm sweater, some nice ripped jeans, a scarf, and boots ๐Ÿ™‚

  106. I’d wear a sweater and jeans.