I love anything plaid, from tops to skirts and even scarves. I also really like the boyfriend style, which is basically anything that's kinda long and loose, like a guy would wear, but much cuter. So I had to include the AE Plaid Western Boyfriend Shirt ($39.50). I love it in pink, and it would look amazing over a pair of long black leggings and tucked into some rugged boots, such as the AE Lace-Up Moto boots.
I'm a sucker for anything destructed, so I love Gilly Hicks's Narrabeen denim shorts ($19.89). The rips, tears and cuffs add to its tough appeal, and would look great with a girly tee, such as Mort Bay ($15.50) in white.
Dresses aren't usually thought of as outdoorsy, but this one definitely is--the Hollister Santa Margarita dress ($39.50) in blue plaid. It has a look that's part lumberjack, part adorable. I would totally pair it with a little denim jacket, such as Lake Hodges ($89.50). The collar and inside are lined with faux sherpa, so it looks authentically-rough.