It used to be hard to wear jeans with boots, but with the trend of skinny jeans, it is much easier wear boots over jeans. You can wear almost any boot over a pair of skinny jeans. If you just aren't into skinny jeans, wear a jean with a tapered leg. Cuts like boot-cut or wide leg will bunch under your boot, making it uncomfortable.
These boots were designed to go over fitted riding trousers. You can wear riding boots over skinny jeans. If you have a skinny calf, you can wear riding boots with jeans that have a fuller leg. Riding boots will come up just below the knee. Riding boots with an adjustable strap on the calf will work well so that your jeans don't bunch up under your boot.
Slouch boots have more slack in the calf and can accommodate a larger pant leg. In addition to a skinny jean, you can wear a tapered leg pant or possibly even a straight leg cut. A slouch boot that comes mid-calf, like UGG Australia, is going to give you more room for your jeans than a boot that comes up higher.
Skinny jeans with over-the-knee boots can be seen in many major fashion magazines. You can try this look even if you don't have a supermodel's figure. Choose a skinny jean with stretch material. When choosing an over-the-knee boot, choose a boot that has stretch in the calf. You can find boots where the shaft of the boot is made out of legwarmer material, or boots with elastic in the calf.
Boots that were made for skiing have more room, and you could certainly wear jeans underneath them. Don't be afraid to wear ski boots when you aren't skiing --- every trend has to start somewhere.
In the late '90s, Timberland boots were a popular trend among teenagers wearing baggy jeans. These short ankle-length boots are also made for construction workers. You can wear work boots as a fashion trend as long as they are neat and clean and don't have evidence of your job on them, such as paint or concrete.
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