The chart below shows some options for boots and booties + jeans. These are just a few of the many, many combos you can make. Read below for more details and choices.
Straight Leg Jeans: choose a bootie that does not come up too high on the ankle. Something with a lower vamp, that even shows a bit of skin, will elongate your leg when wearing a straight jean. Conversely, don’t be afraid to ‘scrunch’ up the straight leg over a combat style boot.
Skinny jeans: choose just about any boot or bootie you like. These jeans are great for wearing under tall boots (to the knee or over the knee). Remember to wear more volume on top when you do that. For booties, these skinny jeans can be tucked into or worn over top. See the pictures above for ideas.
Full length Mini-bells, Flared, Wide-leg: choose a boot or bootie that comes up higher on your ankle, even to mid-calf, so that the jeans fall easily over top. You want to see the toe and heel of the boot/bootie. One of my favorite, super-comfy options for this style of pants is a pair of cowboy boots.
Cropped-Kicks or Boy-friend Jeans: choose a bootie that complements the particular length of the jean. The visual effect you’re going for is not too much skin exposed from the end of the jean to the top of the bootie. So, if your jeans end a bit higher up on the leg, then wear a bootie that comes up above the ankle. These shorter jeans are excellent for showing off a unique and interesting boot. And again to the contrary, you could choose a black cropped kick jean and a black mid-calf boot—allowing the jean to fall over the top of the boot even though the jean is shorter than full length. This looks very modern and elongates the leg.
Vince Camuto black bootie with buckle, Stuart Weitzman leopard print bootie, Nine West light suede cowboy bootie, Gianvito Rossi black quilted leather boot. Outfit images: Netaporter.com and my clients.