After seeing boyfriend jeans pop-up everywhere last fall, I decided to invest in a pair of boyfriend jeans from Madewell. Adding a pair of light-wash, ripped jeans to my wardrobe has helped break up the monotony of skinny jean after skinny jean. But, I am not one to invest a lot of money into a trend that could easily die out after a season or two. I shop strategically, spending more on long-term staple pieces and less on trendier items. That is why I found these high-quality boyfriend jeans all under $100.