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For a fun and flirty look, try pairing a printed sundress with cowboy boots and a straw hat. Add some silver jewelry to really stand out from the crowd. For a more modern take on the cowgirl look, try pairing skinny jeans with a chambray shirt and cowboy boots. Add a felt hat for an extra touch of Western flair. If you want to show off your curves, try wearing a fitted cowboy shirt with a pair of bootcut jeans. Don't forget to add a wide-brimmed hat to complete the look! If you're looking for some cowgirl outfit ideas, you've come to the right place! I have put together a list of top favorite cowgirl looks to help inspire your next western-themed outfit. #1. A classic denim skirt is a must-have for any cowgirl wardrobe. Pair it with a plaid shirt and cowboy boots for a timeless look.