10 FALL OUTFITS - Easy, Comfortable, and Cold Weather Friendly!

Sharon of Her Simple Sole is showcasing fall outfits that are easy, comfortable and cold weather friendly | minimalist outfits | simple outfit ideas | easy fall outfit | transitional winter look

Hey friends! This week’s post is a short and sweet one. I’m featuring 10 fall outfits that are easy and comfortable. Ones that would also work perfectly for the upcoming winter season (with the addition of a jacket/coat over some of the looks, of course!). Let me know which of the 10 outfits is your favourite! For more outfit inspiration, check out these 10 fall outfits with 1 t-shirt.

Some items showcased are PR products or were received as a part of a previous collaboration (labeled as c/o). As well, some links used in this post are affiliate links. This means if you purchase through them, I may earn a small commission at no extra cost to you. My goal is to inspire you to get creative with what you already have and be intentional with adding quality pieces you’ll love for years to come. Thank you for supporting Her Simple Sole blog!

Outfit 1 – Shapeless Dressing

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a a striped cotton sweater, white oversized t-shirt, brown wide-leg pants, slouchy bag and white Stan Smith sneakers | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a striped cotton sweater, white oversized t-shirt, brown wide-leg pants, slouchy bag and gold chunky ring | minimal style, stripe sweater style

Outfit details:
Tradlands Cotton Sweater (XS, c/o, use code HERSIMPLESOLE15 for 15% off your first order)
Madewell Oversized T-Shirt (XS, c/o)
Uniqlo pants (XS)
Adidas sneakers
Poppy Barley bag (c/o)
Jenny Bird ring (c/o)

Outfit 2 – Cool Toned Outfit

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a grey cotton sweater, white t-shirt underneath, grey wide-leg pants, off-white crossbody bag, blue beanie and white sneakers | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a grey cotton sweater, white t-shirt underneath, grey wide-leg pants, off-white crossbody bag | minimal style, cotton sweater look, fall lookbook

Outfit details:
Everlane sweater (XS)
Uniqlo pants (XS)
Uniqlo t-shirt (S)
Madewell beanie (c/o)
Polene bag
Adidas sneakers
Jenny Bird ring (c/o)

Outfit 3 – Dress Down a Shirt

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a brown cashmere wool mockneck sweater, oversized button up shirt underneath, blue straight leg jeans, black slouchy bag and black Converse sneakers | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a brown cashmere wool mockneck sweater, oversized button up shirt underneath, blue straight leg jeans, black slouchy bag and gold chunky ring | minimal style, fall lookbook

Outfit details:
Poppy Barley sweater (XS, c/o)
Able shirt (XS)
Everlane jeans (24, inseam 27.5”)
Converse sneakers
Poppy Barley bag (c/o)
Jenny Bird ring (c/o)

Outfit 4 – Simplified Dressing

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a beige cashmere sweater, grey straight leg jeans, brown tote bag and black ankle boots | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a beige cashmere sweater, grey straight leg jeans, brown tote bag | minimal style, cashmere sweater look

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a beige cashmere sweater, grey straight leg jeans, black maxi bomber jacket, brown tote bag and black ankle boots | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a beige cashmere sweater, grey straight leg jeans, black maxi bomber jacket, brown tote bag | minimalist style | bomber jacket style

Outfit details:
Madewell cashmere sweater (XS, c/o)
Levi’s ribcage jeans (25)
Nisolo boots (c/o)
Samara Tote bag (c/o, use code HERSIMPLESOLE for 10% off; similar styles here and here)
Frank And Oak jacket (XS, c/o)
Jenny Bird ring (c/o)

Outfit 5 – T-shirt and Jeans

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a basic white t-shirt, striped cotton sweater, blue straight leg jeans, cream tote bag and nude ankle boots | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a basic white t-shirt, striped cotton sweater, blue straight leg jeans, cream tote bag and gold chunky ring | minimal style | cream stripes look

Outfit details:
Sezane sweater (XS)
Abercrombie & Fitch t-shirt (S)
Everlane ‘90s Cheeky Jean (24, 26.5” inseam)
L’intervalle boots (linked to similar style, also similar here)
Madewell bag (c/o)
Jenny Bird ring (c/o)

Outfit 6 – Black Monochrome Base

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a cream cotton cardigan over the shoulders, black long sleeve top, black cropped trousers, taupe bucket bag and cream chunky boots | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a cream cotton cardigan over the shoulders, black long sleeve top, black cropped trousers, taupe bucket bag and gold ring | minimal style | sweater over the shoulders

Sharon of Her Simple Sole is showcasing 1 of 10 fall outfits featuring a navy cashmere coat, cream cotton cardigan over the shoulders, black long sleeve top, black cropped trousers, taupe bucket bag and cream chunky boots | minimalist outfits | simple outfit ideas | easy fall outfit

Close-up detailed outfit shot of Sharon of Her Simple Sole wearing a navy cashmere coat, cream cotton cardigan over the shoulders, black long sleeve top, black cropped trousers, taupe bucket bag and gold chunky ring | minimal style | navy cashmere coat look

Outfit details:
KOTN fitted longsleeve (S),
Aritzia pants (linked to similar style, also similar here)
Tradlands cardigan (XS, c/o, use code HERSIMPLESOLE15 for 15% off your first order)
The Curated coat (XXS, c/o, similar styles here and here)
Poppy Barley boots (c/o, linked to available colour, see similar style here)
Paris 64 bag (c/o, similar styles here and here)
Jenny Bird ring (c/o)