The Saturday Early Show has pondered this quandry and we turned to a fashion expert, Sarah Shirley, for help.
Long gone are the days when there were just a few popular brands: Lee jeans, Levis and - in the '80s - the Calvin Klein jeans popularized by Brooke Shields.
Now, there are so many brands of jeans, in all shapes, colors and price points, that there are stores that sell nothing but high-end jeans. It was to one such den of denim, the National Jean Company, that we brought Maggie Rodriguez, and where she tried on more than a dozen pairs until she found one that worked well for her figure - slender and petite.
We asked Shirley to help find jeans for four women with very different body types - curvy, thick around the middle, petite and boyish. Though jeans can range in price from $30 up to $500, we asked her to focus on jeans that cost less than $100.
When shopping for denim, she says, "Be patient. Plan on spending at least an hour trying on different brands, so you can compare different fits and sizes."
We asked her where we ought to begin our jean journey. "Department stores like Bloomingdales have tons of premium denim and premium prices. But vertical retailers like the Gap, Old Navy, Express and Lane Bryant are great places to find jeans. J.C. Penny has partnered with Chip and Pepper to make a lower priced premium jean." She added that Target is similarly partnered with Rock and Republic to do a lower priced denim line as well.
Avoid boot cut or over-flared jeans that have a lot of excess fabric at the bottom and are tighter at the top.
Shirley dressed Gabrielle in Levi's Skinny Straight Jean in a Medium Wash, (www.levis.com) and paired them with a long slouchy turtleneck from Uniqlo and a pair of Miu Miu boots.
Avoid a straight leg jean if you have no curves - this will make you look like a stick.
Shirley dressed Kenya in Uniqlo's Wide Leg Fit $59.50 (www.uniqlo.com) and paired them with a Milly Cheetah spots-on-silk twill bateaux neck top (www.millyny.com) and Franco Sarto shoes.
Avoid small and flap pockets and look for larger flat pockets with not too much detailing on the back. Also, avoid large pockets on the front as well, said Shirley.
Shirley put Melissa in Venezia Jeans from Lane Bryant $39.50 (www.rightfit.com, the Lane Bryant interactive Web site that includes a quick and easy-to-use size calculator to help a customer discover her best size, shape and color). The jeans were paired with a Uniqlo fitted blazer, Steve Madden clutch and shoes, and Tarina Tarantino jewelry.
Avoid, "like the plague, low-rise jeans paired with flimsy T-shirts that show your muffin top bakery in full!" said Shirley. "Look for tops that will give you some structure like a great blouse that is ruched through the mid section."
She put model Patrinilla in Bisou Bisou Michele Bohbot Dark Denim Jeans, $44.00, from J.C. Penny (www.jcp.com) and paired them with a boxy-cut double breasted knit jacket from Uniqlo and shoes from Issac Mizrahi for Target.
Shoes: target.com, francosarto.com;
Shoes and Bags: stevemadden.com;
Tops: anthropologie.com, www.millyny.com, and uniqlo.com.