I meet new people all the time – new and prospective clients, networking contacts, other business owners, etc. And since I’m a stylist, I get asked a lot of clothing-related questions – some of them are specific and personal, and others are general ones that I’m consistently asked over and over. So, what do you think is the question I get asked most often at this time of year?

 “How do I wear jeans with booties?”

This question isn’t about style choices and it isn’t related to creating cute fall/winter outfits with booties – it’s simply about how to wear ankle boots with different kinds of jeans. What do you do if the jeans are too long? Should you stick the jeans down into the booties? When do you cuff? How do you cuff? What kinds of booties work with which types of jeans? So, to provide answers to (hopefully) all of your questions, here’s a quick primer on how to wear different styles of jeans with the ankle booties that you may already have in your closet.

SKINNY JEANS

Skinny jeans have been pervasive in fashion for years. And the assumption that’s most often made is that you should stick the hem of your skinny jeans down into the top of your booties – that works with knee high and over the knee boots just fine, but not with ankle booties. If you stick the hem of your jeans down into your top of your ankle booties, the hem of your jeans may come untucked as you walk or sit, or you may have a big puddle of denim at your ankle that you’re constantly adjusting and readjusting. And who wants to do that?

The ideal skinny jean/bootie combo is when the hem of your jeans grazes the top of your booties (or just a little skin is showing). And that sounds great – but you can’t have different length jeans that graze the top of your many booties, right? So, the solution is a cuff.

You can simply cuff your jeans so that the hem just grazes the top of your booties when you’re standing still. And then, as you sit or stride down the street, you’ll see a little skin. This works for any skinny or slim leg jean (even slim boyfriend jeans). My preferred cuff is a small-ish one (probably a half to three quarters of an inch) – but if you prefer a thicker cuff, go for it! You may need to cuff the hem of your jeans more than once, and you’ll definitely have to adjust your cuff based on which booties you’re wearing today.  

STRAIGHT LEG JEANS

‘Straight leg’ is a term that’s tossed around a lot with jeans, but it doesn’t always mean the same thing. For some brands, it’s jeans that are basically skinny, but don’t hug your ankle super tightly. With other brands, it’s a consistent leg width all the way from hip (or knee) to hem. And still other brands fall somewhere in between.

The true tell of whether a jean is ‘straight’ or not is to take bottom hem and fold it up to the knee. If it’s the same width, then it’s a true straight leg. If it’s wider, then it’s more of a boot, and if it’s narrower, then it’s more of a slim or skinny style. So, when figuring out how to wear your ankle booties with straight leg jeans – if it’s a slimmer leg, check out my tips above. If it has a wider leg opening, check out my tips below. And if you’re not sure which jeans work for your body type, check out my ‘Ask Paul’ virtual service where we can figure it out! (In one hour I helped a client determine which jeans in her closet fit her best and what styles she needs to shop for.)

BOOTCUT & FLARE LEG JEANS

With wider leg openings, it’s not about cuffing or the hem grazing the top of your booties. These jeans are normally worn longer, so the most comfortable way to wear them is when the shaft of the bootie goes up under the leg of the jeans. And this works best when the shaft of the bootie (in other words, the part that goes up your ankle) hugs closely to your ankles. Sock booties are best for this, but this works with any bootie that has a slim shaft. The point is that the hem of your jeans doesn’t get caught on the top of your booties as you walk.

And a quick note on the length of bootcut and flare leg jeans – they should be long enough so that the front hem reaches the top of your bootie near your toes, and the back hem is at least midway down the heel (like in the above photo). But they shouldn’t be too long so that extra denim puddles at the top near your toes, and definitely not so long that the back hem drags on the floor. Make sense?

CROPPED JEANS

Cropped straight or flare jeans are on trend right now, and they’re pretty darn cute. And since they have a wider leg opening, they follow the guidelines for boot/flare leg jeans – ideally, the bootie shaft slides up under the jeans. But since these jeans are cropped, that might not always work – so it’s totally okay if a little skin shows. But if you’re showing over an inch of skin, the jeans are probably too short for the booties. Booties that are snug to your ankle are best with cropped jeans, too, to minimize the jeans getting stuck on the top of your booties. And if your denim wardrobe is lacking and it’s finally time to find jeans that work for your body and your lifestyle, read about my virtual services here where we can create a wardrobe that feels great and expresses your true personal style.

And while I’m on the topic of booties, I can’t not talk about spraying your shoes. You should spray any leather or suede shoe or boot with a stain/waterproofing spray. You can find these sprays where shoes are sold, or at your local drugstore or big box store. How often you spray depends on how often you’re wearing them – spray once a month if you’re wearing your shoes 2-3 times a week, and once a quarter if you’re wearing them 2-3 times a month. I don’t recommend wearing light colored leathers or any suedes in inclement weather – but the spray will at least minimize damage if you’re caught in unexpected precipitation. Also, some shoe brands (like Aquatalia and Blondo) already come with the shoes waterproofed – so read about your shoes before you buy them.

I posted about this topic on my Instagram stories (follow me here on Instagram) and got some questions about how to wear booties:

How do I wear dresses and skirts with various boots? In cold weather, tights are the best way to wear boots with skirts and dresses. Regarding colors – match either your skirt/dress, or your boots (whichever is easier). And if your dress is printed, match the darkest neutral in the print. If you don’t want to wear tights – choose a bootie in a shade similar to your skin tone to create a long and lean leg line.

How do you know if a boot is too big in the ankles? Some booties are designed to be bigger in the ankles, just be aware of how you’re going to wear them before you buy them. Generally, a bootie that hugs your ankles (but doesn’t hurt) will create a longer and leaner leg line, since it follows the shape of your legs.

What about when the boots are so cute but you can’t actually walk in them? Don’t buy them!

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