20 Preppy Fall Outfits

HAPPY OCTOBER. How on earth is it October already? I swear it feels like it was May about a week ago. October is one of my favorite months for outfit planning because #plaid. But also because I can dip into my cool weather wardrobe without having to bundle up.

To celebrate the new month, I’ve rounded up twenty of my favorite fall outfits from past years. Since they’re old outfits, a lot of the pieces are no longer available. I’ve done my best to find similar options so you can recreate on your own if you want! Do you have a favorite?

Get the look: Cardigan Sweater + Tweed Skirt + Button Up + Flats

Field Jacket + Striped Tee + Skinny Jeans + Loafers + Tote

Plaid Shirt + Vest + Skirt + Booties

Barbour + Sweater + Jeans + Boots

Barbour + Scarf + Jeans + Converse + Sunnies

Barbour + SweaterScarf + Jeans + Boots

Plaid Shirt + Vest + Jeans + Boots

Trench + Shirt + Jeans + Flats

Plaid Shirt + Vest + Tote + Boots

Plaid Shirt + Vest + Skirt + Boots

Hat + Peplum Top + Black Pants

Striped Shirt + White Jeans + Vest + Scarf

Barbour + Sweater + Boots

Sweater + Gingham Shirt + Skirt + Boots

Barbour + Plaid Shirt + Sweater

Plaid Shirt + Sweater + Jeans + Boots + Bag

Plaid Shirt + Vest + Jeans + Boots

Quilted Jacket + Shirt + Pants + Flats

Shawl + Shirt + Black Pants + Tassel Earrings

Quilted Jacket + Chambray Shirt + Plaid Skirt + Loafers

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I love the look of your Hillflint Georgetown sweater, Carly! How do you like it? I’ve had my eye on one for the University of Michigan for a while and haven’t pulled the trigger yet.

Gillian Redstone

It seems like you have a few Barbour jackets in different colors…if I want to get my first one, what color would you recommend? Thanks Carly!!


Love the Barbour looks!! What size do you wear in the beadnell? Do you have room to layer?

Sierra Painter

I just found your blog recently and I’m obsessed! I love your style and I just cannot handle these outfits!!😍 fall outfits are seriously MY FAV. I have to say I think my favorite one you’ve shown is the classic striped shirt with the army green jacket….um yes. please. cannot wait to read more! 🙂


any advice on dealing with a breakup? (only ask bc you’ve gave great advice in the past! and life is rough. )

Kristen from Pugs & Pearls

I love this post! You’ve shared some amazing outfits over the years! After seeing them all lined up, I think my favorite looks are the ones with your Barbour jackets. Just got one myself this year so I can’t wait to need it!