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10 Modest Fall Outfit Ideas for Crisp October Days

October 07, 2025 · by Andrea Long

There’s something magical about October—the golden leaves, the warm drinks, and of course, the chance to break out all those layered looks we’ve been waiting for since summer. If you’re searching for stylish, modest outfit ideas to keep you cozy and confident this fall, you’re in the right place.

Here are 10 modest fall outfit ideas that are perfect for those crisp, breezy October days:

1. Oversized Sweater + Midi Skirt + Ankle Boots

Start simple with an oversized knit sweater tucked into a flowy midi skirt. This combo blends comfort and elegance perfectly. Pair with ankle boots and a crossbody bag for an effortless daytime look.

2. Longline Coat + Tailored Midi Dress

A structured long coat instantly elevates any outfit. Layer it over a tailored or A-line midi dress for a modest, tailored look. Finish with loafers or block-heeled boots.


3. Knit Dress + Belt + Tall Boots

Knit dresses are fall staples. Choose a midi or maxi length, add a waist belt for shape, and pair with tall boots for added warmth and style. Add a scarf for an extra cozy layer.

4. Denim Jacket + Maxi Dress + Sneakers

A denim jacket is perfect for transitional weather. Layer it over a patterned or solid-colored maxi dress and add white sneakers for a laid-back weekend outfit.

5. Layered Neutrals: Cardigan + Midi Dress

Layer a neutral-toned cardigan over a classy midi dress in the same color family. Keep the palette soft (think cream, tan, olive) for a serene, modest vibe.

6. Duster Coat + Casual Cotton Dress + Loafers

Cotton fall midi dresses are cozy yet chic. Throw on a duster coat and slip into loafers or mules. Perfect for brunch or a museum stroll.

7. Blazer + Turtleneck Sweater Dress + Scarf

Blazers bring a professional edge. Wear one over a midi turtleneck dress with tights and boots. Add a chunky scarf for both style and warmth.

8. Chunky Cardigan + Floral Dress + Ankle Boots

Cozy up with a chunky cardigan over a classy, fall floral dress. Pair with ankle boots for a polished finish.

9. Modest Shirt Dress + Chic Hat + Heels

For a feminine, dainty look, pair a fall shirt dress with cute heels and a fun handbag. Top with a sweet fall hat for that classic autumn look.

10. Trench Coat + Pleated Dress

A timeless trench adds a polished touch to your fall wardrobe. Wear it over a classy, midi pleated dress. Complete the look with tights and Mary Janes or low block heels. Add a chic beret for an extra bit of pizzazz!

Style Tips for a Modest Fall Wardrobe

  • Layer smart: Lightweight layers help you adjust throughout the day.
  • Play with texture: Knit, wool, suede, and denim add visual interest.
  • Earth tones win: Rust, mustard, olive, taupe, and burgundy always feel right in fall.
  • Don’t forget accessories: Hats, scarves, and structured bags bring everything together.

Whether you're sipping cider at a fall festival or heading to the office, these modest fall outfits will keep you warm, stylish, and true to your values. Which look will you try first?

Andrea Long

About Andrea Long

Andrea Long is wife to Clinton and mommy to Clark and Chantry. She is editor and manager of The Dainty Jewells Blog and part of the marketing team of Dainty Jewells. She is also a Registered Nurse turned stay-at-home mom of her two precious boys. Her life is full of adventure as she travels full-time with her evangelist husband and little ones in a "tiny home on wheels". She enjoys decorating her small space, time with her family, holistic health, a good book, a strong cup of coffee, and as much time at her piano as possible. Andrea considers herself very blessed to live this life for her Faithful Friend. Follow Andrea on Instagram @andreagrindlelong.

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