I get a ton of questions about pant lengths and what shoes to wear with different style pants. The good news is that there are many options out there to suit various body types and tastes, but with all the options also comes lots of confusion.

For our purposes, I’m going to focus on the 4 main pant styles my clients tend to wear, and attempt to simplify things and give you some good rules of thumb and guidelines.

In the end though, the important thing is to wear what YOU like and feel best in.

If you are unsure, take a mirror selfie –  “The selfie doesn’t lie” -and is a better way to see if something works vs. just looking in the mirror.  I don’t know why that is – but it’s true; trust me.

If you have specific questions, shoot me an email, or better yet, head over to the free #justgetdressed Facebook group and ask. It’s filled with likeminded style-oriented (but not fashion-obsessed) women who are eager to share tips and advice!

Ok, here we go…

Pant Style: SKINNY

Skinny jeans and pants  fit snugly from the hips all the way down.  They look best when the hem hits right at the ankle bone. The beauty of skinny pants is that most types of shoes will work with them without having to adjust the length.  This is probably why they’ve remained popular for so long.

Everything from booties to loafers, heels to ballet flats, sandals to wedges and tall boots all work with skinny jeans. Skinny jeans are easy to cuff too, allowing you to play with the length and adjust it to your shoes.  With booties, they look best when they hit the top of the bootie shaft.  This style is easy to wear tucked into tall boots too.

Not everyone has embraced the skinny jeans, which is fine.  They tend to look best on women with a more balanced shape and those with thinner leges, but this is not a hard and fast rule. If you have thicker legs or are heavier on the bottom (i.e. a pear shape) you may look better in a straight leg style that will give the similar appearance as a skinny and with the same shoe flexibility.  But don’t be afraid to try a quality skinny jean. When styled correctly (I.e. with a longer top or layer) skinny jeans in a sleek, dark wash, can be a very versatile and flattering option.



Straight leg pants aren’t as tight to the body as skinny jeans, instead they they skim the legs from hip to hem.  Straight leg styles should hit just below the ankle. However, you’ll see lots of current straight leg jeans with frayed hems cut to or just above the ankle as well.

Like their skinny cousin,  you can wear straight leges with all shoe styles, and they are flattering on most body types. As mentioned earlier, straight leg styles are great for pear and hour glass body-types who prefer the looser fit of straight leg jeans vs. skinny.

The key to wearing straight leg jeans with booties is that the pant leg needs to be wide enough and the boot shaft narrow enough that the pants don’t bunch or get stuck on the boot. Cuffing the jeans is an easy way to get this to work without having to hem them.

With trousers especially, it is important that straight legs don’t puddle on the top of your foot. Hem straight leg pants to fall just below the ankle bone, giving you the most flexibility with shoe styles: pumps, loafers, booties and heels.  Take the shoe you plan to wear with them to the tailor with you!


Pant Style: Bootcut and Flare

Bootcut pants or jeans are fitted through the thighs and flare out slightly from knee to hem (the degree of the flare varies from baby bootcut to wider flares.) They should hit  ¼” to ½” from the floor so it’s important to take into account the shoe you will wear with them. Unlike the other styles, there is really no flexibility here.

Bootcut styles look best with a heel –  try heeled booties,  open toe booties and heeled sandals and wedge or block heels.   If you wear bootcut pants or jeans with flats, I recommend a shoe with a pointed toe to visually elongate the line of the leg, but this is not ideal, unless you are very tall.

And I’m laying down ONE hard rule here (take it or leave it) but please, no sneakers with bootcut jeans.

Bootcut pants and jeans are flattering on many figures and help to balance out a heavier lower body.  When  you wear them with heels and have them hemmed to the correct length, they can make your legs look a mile long. Remember to keep your top shorter or tucked/half-tucked to balance out the longer, wider pant silhouette.


Pant Style: Ankle 

I think the most modern, versatile and easiest to fit and style pant length is the ankle pant. Showing some skin at the slimmest part of your leg is universally flattering and a very current, on-trend look.

Ankle pants should end just above or below the ankle bone depending on where the thinnest part of your lower leg is.  If you have thicker or shorter legs, you may look best with your ankle pants hemmed near the bottom of the ankle bone. If you have longer, thinner legs, you may prefer them above the ankle bone.

The best part about ankle length pants is that they can  be skinny, straight, or bootcut/flare and , you can wear just about any type of shoe with them without having to change the length.

I hear you cold-weather girls though…What to do when it’s too cold to bare your ankles?

If you’ve cuffed your straight leg or skinny jeans to ankle length, you can simply uncuff them to get more length and wear them with your booties.  Or opt for a higher shaft sock bootie to get the coverage you want and create an unbroken, sleek, flattering line. (See the pic in the Straight Leg section of blogger Jo-Lynne Shane wearing ankle length, straight-leg jeans and sock booties).

For a fun, casual look on cold days, I love the look of socks showing with your booties too. Be sure you are intentional with your choice of socks.  Your safest bet is black or charcoal socks with black booties and gray or tan with neutral booties. I love to wear tan or gray marled socks with my taupe suede booties.  Image below by un-fancy.com.


Hopefully this was helpful! Remember these are guidelines, not hard and fast rules. In the end, wear what YOU like. Play around with different hem lengths and shoes and try new combos using the selfie as your guide.

A great way to get ideas is to do a pinterest search, for example “booties with straight leg jeans”. You can get a lot of inspiration that way and see what looks are currently on trend.

And,  if you’re unsure,  I encourage you to head over to my private and  free VIP Facebook Group. and ask away! We are here to help!

Or…simply post your questions or comments below. What’s your favorite pant length to wear?

Now, go #justgetdressed.