What do you think is my most asked question at this time of year? Is it, “how do I layer for fall?” Or, “which sweaters should I buy right now?” Or, “what dresses can I take into colder weather?”
It’s none of the above. The question I get so often in fall is, “how do I wear booties and jeans?” And with the shift of jeans shapes, it can be even more confusing. A few years ago, it was still all about skinny jeans – and you figured out how to wear booties with those. But now, there are straight leg jeans. And wide leg. And flare and bootcut. And cropped versions of all of these. And how do you know which booties work with which jeans shape?
By no means will I call myself a ‘jeans and booties whisperer’ (although I have been called a ‘wardrobe whisperer’, which is kind of fun). But I can tell you which booties I’m recommending to my clients to work with different kinds of jeans. Because you don’t need a different pair of jeans that go with every pair of booties - or a different pair of booties for every kind of jeans. (If you’re shopping for new jeans, read this first.)
The bootie style that I’m recommending most to clients right now are styles with a slim shaft, that sit higher on your ankle. ‘Slim shaft’ means styles that hug closely to your ankle (as opposed to hovering around it). And ‘higher on your ankle’ means booties that completely cover your ankle bone, plus a couple of inches (as opposed to booties that come just to your ankle bone).
And the reason I’m recommending these is because of their versatility. When a bootie sits closer to your ankle, you can wear it with jeans that stop right above the top of the booties. Or you can wear it with jeans that cover the booties a bit – because the bootie slips right under the leg of the jeans. Or you can wear it with full length jeans (again, because the bootie slips right under the leg of the jeans).
A few styles of slim shaft booties that sit high on your ankle: sock boots by Jeffrey Campbell, elongated almond toe boots by Vince, chelsea boots by Vince
The ultimate version of this kind of bootie is a ‘sock bootie’ – one that’s made of a stretchy fabric that hugs your ankle like a thick sock. Sock booties work great under jeans and pants specifically for that reason – they hug your ankle, so the bottom of your pants don’t get caught on the bootie when you’re walking. And they’re great with skirts and dresses, too – because they don’t interrupt your leg line. Wear a black sock bootie with black tights, and you can’t really tell where the tights end and the booties begin.
But you don’t need to wear sock booties to get the benefit of slim shaft booties. There are many styles out there right now, in different fabrics and shapes and vibes. The main thing to pay attention to is that the top of the bootie hugs your ankle. And that it comes up higher than some booties did in the past.
A point toe bootie is generally my favorite style of slim shaft bootie – mainly for it’s versatility. The point toe visually lengthens your leg, so it’s perfect with all different leg widths (and this also goes for a longer almond or square toe). Wear them with slim and skinny jeans, just like you used to. Wear them with cropped jeans – they’re perfect with cropped straight leg styles. And they’re specifically great with cropped bootcut, flare or wide leg jeans, because the longer toe balances out the width at the bottom of these jeans. And for a similar reason, they’re ideal for full length wide leg or bootcut/flare leg jeans – because the point toe pokes out the front (so it balances proportions better than a shorter, round toe boot does).
Booties are reflecting a bunch of different trends this season - suede round toe by Dolce Vita, metallic western by All Saints, point toe chelsea by Tory Burch
And if you’re not into point toe boots, that’s totally okay! There are slim shaft booties available in rounded toe shapes, too. The most common is a traditional chelsea boot (the ones with elastic panels at the side). I love these with cropped slim/skinny and cropped straight leg styles. And they also work with full length straight leg styles – although I prefer it when you cuff up your jeans a little, to highlight the slimmer part of the ankle.
And one of the best things about any style of slim shaft bootie is that it works great with skirts and dresses. Style-wise, it’s totally your choice if you go for a pointy toe (or another longer toe option) or a rounded toe. But because these styles sit close to your ankle, they’re easy to wear with tights and skirts/dresses all through fall and winter.
Knee high boots in different shapes and heel heights by Veronica Beard, Marc Fisher, Schutz, Vince Camuto
Another question I’ve been getting lately is, “can I still wear my knee high boots?” And the answer is a resounding, “yes!”. I’ve never stopped loving knee high boots (although they were hard to find for a couple of years). They’re another great option with skirts and dresses in colder weather. And they work great with slim and skinny jeans – and even certain straight leg styles. (Click here to see how I outfitted a plaid blazer with knee high boots and a dress, and chelsea boots and cords.)
There are two things I want to remind you of, before I tie this up. First – take any style advice with a grain of salt. If you like to wear booties and jeans different from what I’ve described here, go for it. It’s not about what anyone else says about what you wear – it’s about what makes you feel good. Second – always protect your booties with a stain and waterproofing spray. Spray them once a season if you wear the booties on occasion. And spray them every month if you wear the booties regularly.
Do you have any questions about wearing booties and jeans in fall? Drop them in the comments and I’ll answer as soon as I see them.
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