I get a ton of questions about pant styles and hem lengths and what shoes to wear with the various styles of pants that are trending these days.
I was about to recreate this post, and then I realized, I already had it in my archives! So I updated this post with new pictures and more current information.
The good news is, almost anything goes right now as far as pant styles go, so you should wear the styles that suit YOU best.
The bad news is, with so many options, there are a lot of variables when it comes to putting outfits together. Confused? I am too! Let’s break it down.
Skinnies fit snugly and take the shape of the leg from hips to hem. They look best when the hem falls right around the ankle bone, but in recent years, the trend has been to wear them a little shorter — I like mine right above the ankle bone.
For me, this means a 27″ inseam is about perfect, but sometimes I wear 28″. This will be different for every woman, though, because it depends on your height.
wearing: rag & bone Cate Skinny Ankle Jeans
It’s sometimes hard to find jeans off the rack that are the perfect length, but you can always cut them. See my tutorial on How to Cut Your Jeans.
Skinny jeans looks great with both flats and heels, and just about any shoe style goes from booties to wedge sandals, from ballet flats to pumps, and from loafers to sneakers.
The best part about skinny jeans is, you don’t have to own different lengths to work with different shoes. I’m convinced this is why skinny jeans have maintained their popularity for so long. They’re just so easy.
Skinny jeans are most flattering on women who have more of a balanced hourglass shape and those with longer, thinner legs. If you have thicker legs or are a pear shape, you may look better in a straight leg style.
That said, skinnies are so versatile that I would have a hard time completely eliminating them from my closet, even if I knew I looked better in other styles.
STYLE TIP: Skinny jeans pair well with ankle boots, but there are some variables to consider — length of jean, size of leg opening, as well as the height and width of the boot shaft.
When pairing skinnies with ankle boots, you have a few options:
1) let your jeans fall to the top of the boot and bunch or rest on top; this only works when the length of the jeans and the shaft of the boot just meet.
2) cuff the jeans so they end just above the top of the ankle boots; I prefer this look when the ankle boots have a lower shaft, because it tends to shorten the line of the leg.
3) pull the jeans down over the shaft of the ankle boots; this works best with the sock booties because the shaft is snug to the leg, so the jeans easily fit over top.
4) tuck your skinnies inside; this works best with super skinny jeans that are tight to the ankle and boots with a slightly wider and taller shaft so the jeans fit inside without folding or bunching.
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Straight Leg Jeans
Straight leg pants aren’t as snug to the body as skinnies, but they skim the legs from hip to hem. These are a great alternative to skinny jeans if you aren’t comfortable in pants that are so form-fitting.
For a traditional fit, straight leg styles should be hemmed just below the ankle, right before your foot starts. These pants look best if they don’t break on top of the foot. You can wear straight jeans with all shoe styles, and they are flattering on pretty much every body type.
STYLE TIP: When pairing straight leg jeans with ankle boots, you want your jeans to skim over the top of the boots, so the leg has to be wide enough and the boot shaft narrow enough for this to happen without the jeans bunching or getting “stuck” on the boot shaft.
The exception is with a cropped straight leg jean, or a straight ankle jean, both which are trending right now… In fact, this is a far more modern length for straight leg jeans.
Crop Straight Leg / Ankle Straight Leg Jeans
Cropped is a somewhat nebulous term. Cropped pants fall anywhere between the middle of the calf to the ankle, but I consider them shorter than ankle pants and longer than capris.
Your pants should never end at the widest point of your leg, so you want to hem your cropped pants to a spot where your leg is narrowing. This can be a range, and it is partially dependent on your height and the shape of your leg. Play around with it, and see what looks right to you.
When you figure out your preferred length, it’s a lot easier to shop because you can narrow your choices by inseam measurement, or you can always cut jeans that are a little too long. (See my tutorial on How to Cut Your Jeans.)
How Do I Wear Crop Jeans in the Winter?
wearing: Mother Insider Crop Jeans
Before we move on, I want to address this question that I get A LOT. Because the trend du jour is to show some ankle, it immediately follows that I get questions about what to do when it’s cold outside.
You CAN wear socks with crop and ankle-length jeans, but it just limits your shoe choices to some extent.
With crop straight and ankle straight styles, the easiest thing to do is wear booties with a higher shaft and let the jeans fall over the boots. Then you can wear socks and no one will see them, and no leg is exposed.
YOU MAY ALSO LIKE: Styling Crop Straight Jeans for Winter
You can also do this with boots do not meet the hem of the jeans, and wear socks that coordinate with your outfit.
Flares & Bootcut Jeans
Bootcut pants or jeans are fitted through the thighs and flare out slightly from knee to hem. It’s important to have full-length bootcut jeans hemmed to the correct length with the shoes you will wear with them — which should be ¼” to ½” from the floor. The exception is if you’re wearing a cropped style.
Flares are bootcut jeans that have a wider flare at the bottom. The same rules apply. Kick flares refer to flared crop styles, which is a big trend at the moment. (More on that below.)
Bootcut pants and jeans are pretty much universally flattering, and they’re great for balancing out a top-heavy figure or wide hips. If you wear them with heels and have them hemmed correctly, they make your legs look a mile long.
Full-length bootcut jeans and flares generally look best with a heel (usually pumps or ankle boots) but I also wear mine with peep-toe booties and open toe sandals. 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.
wearing: AG Angel Bootcut Jeans
I lumped the crop flares and demi boot styles in with the pictures above, but their rules are the same as crop straight and ankle straight jeans.
Basically, any length below the widest point of the calf is fine, it just depends on how you want them to fit with the shoes you are wearing.
The pair I’m wearing above is a classic demi-boot crop length pant. (Demi-boot means a narrow bootcut, or a slim bootcut — so they aren’t quite straight, but they’re not a dramatic flare either.) They have a 26″ inseam, which is my favorite inseam length for a crop jean. I can sometimes go to 25″, but any shorter than that, and they would be capris. (These pants also come in petite and tall sizes, FYI.)
The idea of boyfriend jeans is that these slouchy pants look like you may have borrowed them from your boyfriend.
My favorite length for a boyfriend jean is cropped — so, two or three inches above my ankle bone. Typically you cuff your boyfriend jeans to achieve this length, but you can wear them un-cuffed if you prefer.
Boyfriend jeans can be dressed up or down, and these days I see them worn with every type of shoe — from pumps to sneakers, ankle boots to loafers, and even sandals. It just depends on the rest of your outfit and the look you’re going for.
A Few Other Mentions…
Girlfriend Jeans and Slim Boyfriend Jeans are slightly slimmer versions of boyfriend jeans, and the same rules apply. I find a girlfriend jean or “slim boyfriend” more flattering on me personally because they aren’t as sloppy as traditional boyfriend jeans.
What about Capris?
Fun fact: The term “capri pants” is derived from the Italian isle of Capri, where this style rose to popularity in the late 1950s and early ’60s.
These days, capri pants is really just another name for cropped pants, but they’ve come to be associated with the frumpier styles that end at the widest point of the calf, which is never a good idea.
Call them what you will, but make sure your cropped pants/capris end where the leg narrows — that is usually a couple of inches above the ankle bone. (The picture below is no bueno.)
And finally, what about Pedal Pushers?
Originally designed for cyclists who couldn’t pedal in anything that fell far below the knee, these pants are too long to be Bermuda shorts and too short to be cropped pants.
I actually think these pants can be quite flattering — more so than a Bermuda short, actually. (They’re more of a spring and summer pant.)
Pedal pushers are most flattering when they fit close to the thigh, but you’ll also see wider styles from time to time. You can wear them with pretty much any shoe but usually you will see them with a wedge sandal or sneakers or flats.
And I think that pretty much covers all the major categories!!! As always, I’m happy to answer any questions in the comments, and perhaps I can expand on a few of these styles in future posts.
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