Cozy & Chic: Fall Outfit Ideas for Women Over 50 You’ll Love Wearing on Repeat

Ahh Fall… my second favorite season, maybe even my first. 🍂 Last year, I spent a week in Banff, Canada, and I honestly believe it’s one of the most magical places to experience autumn. How can you not fall in love with the fiery orange, golden yellow, and deep red maple leaves? I think I snapped over 50 photos of nothing but maple trees! 😀

But beyond the scenery, fall fashion is truly my favorite. Why? Because it’s the season of layering. The beauty of fall colors—rust, camel, deep greens—paired with neutrals are always at the top of my wardrobe. And the weather is just right: cool enough to layer without feeling over-bundled, with that crisp chill in the air perfect for a weekend stroll in your favorite cozy outfit.

If you’re looking for outfit inspiration this season, here are some chic and timeless fall outfits for women over 50 that you’ll want to wear on repeat.

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1. Tweed Blazer and Wide-Leg Pants

Nothing says timeless elegance like a tweed blazer. Pair it with wide-leg pants and a simple blouse for an outfit that’s both polished and comfortable. This look works beautifully for lunch with friends or even a casual business meeting. Add loafers or block-heel boots to complete your chic fall style.

Shop the Look:

Tweed Jacket - Goelia Tweed Blazer

Wide leg Jeans - Lee Women's High Rise Trouser Jean

Shoes - NINE WEST Women's Pruce Heeled Sandal

2. Cozy Knit Sweaters with Jeggings

Imagine walking in a maple tree filled garden in your cozy knit sweater and jeggings. Pair it with ankle boots and its a picture perfect image.

Shop the Look:

Sweater - SUUKSESS Women Cashmere Sweater

Jeans - KUT from the Kloth Diana Skinny Jeans

Boots - Thursday Boot Company Women's Chelsea Boots

Bag - Coach Mila Crossbody Bag

3. Midi Skirt and Orange Cardigan

If there’s one outfit that truly celebrates the beauty of fall, it’s a flowy midi skirt paired with a cozy orange cardigan. The skirt adds feminine charm, while the cardigan brings that pop of pumpkin-spice warmth we all love this season. Slip on tall boots and a simple necklace, and you’ve got a chic, effortless look that feels just right for a crisp autumn stroll.

Shop the Look:

Skirt - DRESSTELLS Pleated Midi Skirts for Women,

Cardigan - SUUKSESS Women Cashmere Cardigan

Boots - ALDO Women's Block Heel Ankle Boot

4. Maroon Cardigan and Jeggings

A maroon cardigan is a fall wardrobe essential—rich in color and endlessly versatile. Pair it with jeggings for a comfortable yet put-together outfit. Add loafers or booties and a simple gold necklace for an easy, chic look that you’ll want to wear on repeat.

Shop the Look:

Cardigan - VIISHOW Women's Classic Cardigans

Jeans - KUT from the Kloth Diana Skinny Jeans

Boots - Thursday Boot Company Women's Chelsea Boots

5. Cream Sweater and Khaki Pants

Neutral tones never go out of style. A cream sweater paired with khaki pants creates a soft, polished look that feels fresh and modern. Perfect for office or casual get-togethers, this combo is understated elegance at its best. Finish with a cute handbag and beige sandals.

Shop the Look:

Sweater - GreenMount Women's V Neck Sweater

Pants - NIMIN High Waisted Work Pants for Women

Bag - Coach Jonie Bag

Shoes - NINE WEST Women's Pruce Heeled Sandal

6. Essential Blazer and Turtleneck

Sleek and sophisticated, a fitted turtleneck tucked under a blazer is fall power look. Choose warm shades like camel or forest green to embrace the season.

Shop the Look:

Blazer - Mina Self Blazer Jacket

Turtleneck - 100% Merino Wool Turtleneck

Jeans - KUT from the Kloth Diana Skinny Jeans

Boots - Thursday Boot Company Women's Chelsea Boots

Bag - Coach Unisex Lillie Carryall

7. Coatigan and Slim Pants

If you love the comfort of a cardigan but crave the structure of a coat, the coatigan is your fall best friend. Pair it with slim-fit pants and ankle boots for a look that’s polished yet cozy. This outfit is perfect for layering and works beautifully for everyday wear.

Shop the Look:

Coatigan - ANRABESS Coatigan

Jeans - KUT from the Kloth Diana Skinny Jeans

Shoes - Söfft Women's Molly Pump

8. Camel Jacket and Black Jeans

Nothing says autumn like a cozy jacket and boots. For this look, I paired slim black jeans with a cropped brown jacket and the always-cool Doc Martens. It’s the perfect fall jean outfit for women over 50—stylish, comfortable, and season-ready.

Shop the Look:

Jacket - Allegra K Women's Moto Jacket

Jeans - KUT from the Kloth Diana Skinny Jeans

9. Cream Sweater and Maroon Pants with Camel Scarf

This combination is fall perfection—soft, rich, and totally timeless. A cream sweater keeps the look fresh and neutral, while maroon pants add a gorgeous pop of seasonal color. Wrap a camel scarf around your shoulders and you’ve instantly got that cozy-chic vibe. Perfect for weekend outings or even a casual dinner out.

Shop the Look:

Sweater - Sweater - GreenMount Women's V Neck Sweater Pants - Urban CoCo Women's Dress Pants

Scarf - Floralies Cashmere Scarf for Women

10. Grey Blazer and Pants with Green Top

For those days when you want something sleek and polished, go for a grey blazer and matching pants. It’s a classic look that always delivers. Add a green top underneath for a subtle nod to fall’s earthy tones, and finish with loafers or block-heel boots. It’s sophisticated, comfortable, and effortlessly chic—everything fall fashion should be.

Shop the Look:

Blazer - Mina Self 2025 Blazer Jacket

Pants - NIMIN High Waisted Work Pants for Women

Top - Women's Sweater

Shoes - New Balance Women's 550 Sneakers

Final Thoughts: Why Fall is the Best Season to Refresh Your Wardrobe

There’s just something about fall that makes it feel like a fresh start. Maybe it’s the crisp air, the cozy vibes, or the excuse to finally layer without looking like the Michelin man. 😀 Last year, when I was in Banff snapping about 50 photos of maple trees (yes, just the trees!), I realized how perfectly fall fashion reflects the season—rust, camel, deep greens, maroon, and orange everywhere you look.

That’s why fall is the best time to refresh your wardrobe. You get to play with layers, mix in those rich autumn colors, and pull together outfits that feel both stylish and comfortable. And honestly? When you love what you’re wearing, you’ll want to put those looks on repeat all season long. 🍁

✨ Amazon Affiliate Disclosure: As an Amazon Associate, I may earn from qualifying purchases. This comes at no extra cost to you and helps support this blog.