Plaid... in a jacket! Reminds me of the kind of shirts you'd get from fieldmaster clothing. Although the colors are a bit over the top - but this is the runway, it's supposed to be shocking. I think a more wearable look for everyday life would be a plaid pea coat like the one pictured below with jeans and Uggs.
Graphic tees under leather or bomber jackets are really cute too! Not too sure about Ashley's choice of pants or shoes, but the top of the outfit is great. Any kind of graphic tee will do. The more interesting and unique, the better! You can see the swag with the guinness beer price tag of shirts.
Jaime King looks amazing here and I'm in love with her shoes! I really like how she made a masculine looking shoe look very feminine. They look like these harris shoes. I think you could definitely use this type of shoe to as a foundation for some really great fall outfits.