Hello dear reader. Today I’m sharing style tips for one of those fashion necessities: pairing jeans with booties for fall and winter. Whether you live in a warmer or cooler climate, you’re going to want to wear those straight leg jeans that are trending with your booties or shorter boots. And it can be a little tricky. But you’ve got this!
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It just really shouldn’t be this hard to get dressed. Ha! But because we keep fooling around with pants and jean silhouettes and lengths, it does indeed present the fashionable woman with a challenge.
Just a couple of years ago I was offering tips for wearing skinny jeans with booties. And I’ll still be sharing those if I ever get around to wearing the slimmer fitted jeans again. But right now I think many of us are learning to prefer the relaxed fit and silhouette of the straight leg jeans. So we need a little refresher on how to select and style booties with these more traditional jeans.
Lace-Up Boots with Straight Leg Jeans
One great option under straight leg jeans is the classic lace-up boot or bootie.
Just last week I shared this outfit with my favorite straight leg jeans. In this post I mentioned that lace up booties like mine are great for pairing with straight leg jeans because the narrow shaft of the shoes fits nicely under even slimmer straight leg jeans. Honestly, I didn’t wear my Thursday Boot Company Captain boots very often the first year I had them. They don’t work as well with the skinny jeans I was wearing at the time. But as I’ve been wearing more and more straight leg silhouettes, I find myself gravitating to these timeless boots.
So I think the lace-up boots of most varieties will work well with your straight leg jeans, including your chunkier all-weather boots.
Lace-up boots are very on trend right now, and they have a somewhat timeless appeal. If you wan to balance out the masculine effect, just wear something more feminine or a pretty color up top. But, especially when the weather warrants it, these somewhat rugged looking boots will actually look very classic and sharp with your straight leg jeans.
You can get lace-up boots in all sorts of styles, too. My captain boots have that Old English vibe to them. They remind me of what most everyone from school girls to newsies would have worn in jolly old England. But my Sorels below have a little bit more of a lumberjack vibe to them. You can find lace-up boots with faux and genuine shearling, lug or standard soles, waterproofing, additional hardware, zippers for access and more of a hiking vibe.
I can’t seem to find many photos of me wearing my Sorel Boots from last year (shown above), and that really surprises me because I LOVE those boots. But I’m wondering if it’s not because I was wearing more skinny jeans last year. In the photo above I’m actually wearing my fleece lined straight leg pants from Talbots, not straight leg jeans. But I think I just didn’t wear straight leg jeans a lot last year. Wow! How times have changed!
I’m including a shopping widget full of great lace-up booties for your convenience. These are in a wide range of prices and various styles.
Chelsea Boots or Booties with Straight Leg Jeans
Because it’s smart to wear a boot or bootie that will fit up under your straight leg jeans, another good option is the Chelsea bootie. These generally have a high shaft that is narrow enough to fit under the leg of your pants.
I haven’t really had any true Chelsea boots before. Honestly, I didn’t like them. And this silhouette is just not conducive to skinny jeans at all in my opinion. To wear them with skinnies you have to cuff the jeans above the bootie and bare some skin, and I just wasn’t into doing that during the winter, but really anytime. Ha! But now that we’re moving toward more straight leg jeans I actually love the look of the traditional Chelsea boots, especially with a bit of a trending lug sole.
Above and below I’m wearing the Talbots Tish pebbled leather Chelsea boots. I bought them in both colors, black and cognac, and I am beyond happy with them. One of the secrets to finding Chelsea booties that you’ll be happy with is choosing some with soft leather. Since the shaft comes up over the bend in your ankle, you’re going to want something that will bend and flex when you bend and flex. These pebbled leather Chelsea boots from Talbots definitely do that. They are very comfortable and fit true to size.
Chelsea boots got their name from their popularity in Chelsea, a trendy, affluent section of London, during the fifties and sixties. It’s believed that Queen Victoria’s shoemaker crafted the first pair of these pull-on style boots for the queen.
You can see me wearing these pebbled leather Chelsea boots in last week’s video below.
I think you’ll be seeing me style these Chelsea boots a lot this fall and winter. You can find them in varying heights, colors and styles. Lug soles are really trending, but you don’t have to wear them if that’s not your thing. If you live where you get a lot of wet weather during the winter, you might want to look for waterproofed Chelsea boots. For a more economical option that is very similar to my Chelsea boots from Talbots, check out these from Caslon, a Nordstrom brand. They’re also water resistant.
By the way, Chelsea booties are generally pull-on booties. And that always makes me a little wary. Will I be able to get them on and off??? But now that I’ve finally tried them, I can tell you that generally, yes, I can get them on and off quite easily. If Queen Victoria can do it, so can we!
Other High Shaft Booties with Straight Leg Jeans
Of course, you can also try to find other booties with high, narrow shafts. The goal is simply to find boots that you can wear under your jeans leg without fuss and muss. You don’t want the boots to keep slipping out from under your pants leg. And you don’t want the jeans leg to end right at the top of the boot because that causes them to “conflict” with each other. Know how I mean?
When we were wearing a lot of skinny jeans many of us wore shorter shaft booties or we wore booties with a wider shaft so we could tuck the slim jeans leg down inside them. So that’s the shift you need to keep in mind. Now we’re simply taking the jean or pant leg outside of the booties.
The great thing about these style boots is that they often also look good with skirts and dresses. These are a little dressier than a traditional Chelsea boot, too. Chelseas are traditionally very casual pull-on boots, while these of course have more hardware. And they can be a little more form fitting because they do have a zipper entrance.
I’m also really enjoying the Franco Sarto Waxton booties above. They call them a Chelsea bootie, but in the description they concede that they are Chelsea-inspired. They fit beautifully and have a very trendy squared off toe.
Shorter Shaft Booties with Straight Leg Jeans
Maybe I should have tackled this category first and gotten it out of the way. You absolutely can wear your shorter shaft booties with your straight leg jeans, but this is where you’ll run into some issues.
Now in the photo above I’m actually wearing cropped length jeans. But I wanted you to see the height of those booties. They’re from last year and Franco Sarto doesn’t even seem to have a similar bootie this year. The Franco Sarto bootie that most resembles this one is this Dalden bootie and if you click through you’ll notice that it’s a sharp bootie alright, but it has a higher shaft. That’s because boot manufacturers got the memo about straight leg jeans. Ha! These lower shaft booties were more ideal for skinny jeans really.
Now in the photo below from last winter, my jeans are longer. And it was cold! So I wore socks. But I really didn’t want those socks to show. I don’t think I even bothered to wear black socks, which I probably should have done. (I probably just forgot to take them with me on the photo shoot.) But you can see here why the lower shaft bootie presents some problems.
So the bad news is that if you have low shaft booties like these (I kept mine and love them) and want to wear them, it will be a little more challenging. Ideally you would just not wear socks and you’d bare a little ankle like I did above.
The good news is that if your ankles have been freezing in years past, they don’t have to any longer. We’re finding plenty of high shaft booties on the market that will fit nicely under your straight leg jeans. And that’s just another great reason to make the switch to those straight leg jeans in my opinion.
By the way, the one thing you don’t want to do with straight leg jeans is attempt to wear full length or knee high boots with them. We’ll still be better off wearing our riding boots and other knee high boots with either skinny jeans, leggings, skirts, dresses or, in some cases, trousers and bootcut jeans. But don’t try to cram your straight leg jeans into boots and don’t attempt to wear your riding boots under them either.
Tell you what, let’s end with a photo of me doing it right. Ha! Here’s another look at how straight leg jeans can look really great over the right pair of boots.
Thanks so much for stopping in today. I hope this post helps us all to rock those straight leg jeans and booties this fall and winter. If you have questions, let me know. I may have neglected to answer some prevailing questions. I’m on Sudafed today and that makes me a little loopy, so no telling what I did here to tell you the truth. Ha! Have a good one!
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Blessed for My Day
Every day we serve someone. We either serve ourselves or God. Did you think I was going to suggest that we sometimes serve others? I’ve found that when we get into the habit of bending over backwards for someone – be it a boss, a spouse, a mother, whomever – we’re really serving ourselves. People pleasing is just a way of preserving our comfort and earning accolades that feed the ego.
But Joshua 24:15 encourages us to choose today to serve the Lord. When we serve the Lord we die to self and we follow His marching orders. Those directives may indeed lead us to serve other people, but this time it will be with true sacrifice and grace, not self-serving greed. Who will you serve today?
“But if it is disagreeable in your sight to serve the Lord, choose for yourselves today whom you will serve: whether the gods which your fathers served, which were beyond the Euphrates River, or the gods of the Amorites in whose land you are living; but as for me and my house, we will serve the Lord.” ~ Joshua 24:15