The Cowboy: Great for all body types. May be difficult to find a good fit if you have muscular calves.
This is my steadfast. You can wear it with dresses or jeans. The important aspect of making this purchase is that you buy ONLY something that is comfortable! There isn't anything worse than a boot that's uncomfortable. First it's going to make you walk funny which looks funny and that's NOT stylish! I personally like a narrow 'shaft' or body of a boot since have a narrow calf. Cowboy boots can be worn though with a wider shaft. If you have a wide calf a wider shaft will look more flattering than one that's tight on your calf. Not a good fit. You should be able to at least put a finger in the front and the back.
Embellishment on a cowboy boot can be cute but not for an everyday boot and it can look a little cheesy.
Ankle Cowboy: Good for longer legs and average to skinny ankles
This is a great boot and can really be very stylish. Again, buy quality and make sure you've got comfort. This boot isn't great for you if you have a wider ankle, it can make your leg look wider and cuts you off.
Same if you have short legs. This style can cut your leg off and make you look shorter than you are.
Pair with leggings or skinny jeans. Under your favorite jeans or with a casual dress.
The Motorcycle: Avoid if you have 'thicker' legs.
So on trend right now and one of my favorites but it's not for everyone. If you tend to dress more classically then this boot may not translate well into your wardrobe. It's a great boot for a my eclectic or trendy fashionistas wardrobe.
Looks great paired with a casual dress or over jeans. I do find it's a difficult boot to wear under jeans or pants because they usually have a wider shaft which can get caught up in the jean and disturbs the drape of your pant.
This isn't the best boot for you either if you have a wider ankle and calf.
The Classic: Great for ALL body types
If this is the case than a classic boot with shape at the ankle is best for your body type. It will define more shape at your ankle and compliment your leg shape. You can find boot shafts at different widths. You can always measure your calf as most sites will offer your the width of the shaft.
You want to look for leather NOT pleather and quality. It's better to spend good money for a good boot that will last you season after season instead of a cheap boot that looks cheap and won't last you very long.
You want the toe piece to be wide enough for comfort but sleek and stylish enough to compliment your foot. I always suggest a pointier toe to elongate your leg. If you think pointy shoes aren't comfortable then try a pair on one 1/2 size larger than your regular size. Pointy shoes can be comfortable I promise.
And the boot shaft should be skimming on your leg. Not too tight but absolutely not too large. Too large is an obvious ill fit.
Riding Boot: Good for ALL body types
The riding boot is another classic, though it's not styled quite as sleek as The Classic. The toe piece is generally a little wider and they most often come in a 1" heel.
the riding boot is GREAT to wear over jeans with an boyfriend cardigan or countered with a feminine but casual dress.
Make sure there is a shape at the ankle and the shaft is skimming your leg without being too tight or loss.
This IS a boot you want to invest in! I spent $175 for a pair of riding boots from Jcrew about 7 years ago and I STILL rock them! They are worn so perfectly and are SO comfortable!
Over the Knee: Great if you have long legs.
So on trend right now! This is a great and stylish boot if you have long legs! If you have shorter legs then I don't think this will be the most flattering for your figure. Being that it will hit above your knee, you want to make sure that it's not making your legs look shorter.
Pair this boot over a jean, legging or tight. It works with pants or dresses. You can invest in the over the knee because it ALWAYS comes back on trend. You want to keep the boot classic with little embellishment. It's enough drama that it's over the knee. Anything more can look a little trashy. Make sure you buy real leather and quality. You should be able to find these starting to go on sale soon. I know I've got my eyes open for that:)
The question of weather to buy black or brown is always a question I get and I do suggest one of each. I think black can be more formal and brown more casual. I do believe it's good to have a classic boot in both black and brown, especially if you're a classic style. They can be worn with EVERYTHING from skirts and suits to jeans and leggings.