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Wearing Straight Leg Jeans with Booties this Fall & Winter

November 9, 2021

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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Wearing Straight Leg Jeans with Booties this Fall and Winter

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.

Favorite Fall Outfit from My Closet
Captain boots // See the original post for more details.

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.

Winter classics Outfit with Black and Red
my boots from last year available in just a few sizes at a great price // similar boots // See the original post for details.

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.

Lace Up Booties
Captain boots

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.

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My Sorel Boots from last year still available in just a few sizes // This year’s model of the same shoe

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.

Chelsea Booties under Straight Jeans
Chelsea Booties // tote // jeans // sweater // vest

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 Booties under Straight Jeans
See the video for more information // wearing the pebbled leather Chelsea boots from Talbots

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?

Straight Leg Jeans with High Shaft Booties
similar boots at Talbots, where I got these last year // similar boots from Macy’s

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 boots I’m wearing above are from Talbots last year and they’re no longer available. But these at Talbots would probably wear similarly. And these would, too.

High Shaft Booties Under Straight Leg Jeans

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.

Wear a Shirt Jacket with a Colored top
my boots // See the post for more details.

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.

Shorter Shaft Booties
See the original post for details. Boots no longer available.

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.

Winter Classic Outfit with Black & Grey
See the original post for details.

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

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xoxo, Kay
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18 thoughts on “Wearing Straight Leg Jeans with Booties this Fall & Winter

  1. Hi Kay. Great post. I am so glad straight leg jeans are in style now. In regards to the Always Pan, I ordered 2 yesterday at a cost of $99 each (Christmas gifts) – the Our Place website. Last week I ordered the duo (for myself) with the savings offered. Hope you are healing well from your surgery. Have a great day.

    1. Hi Peggy. I hope you and the others for whom you purchased the Always Pan enjoy it as much as I do. I used mine last night to make chili for James and me. And I thought to myself that my favorite thing about the pan (besides that handy spoon rest!) is that it cleans up like a dream. ?

  2. Great tip on straight leg jeans and higher boots like Chelsea boots. I guess I really didn’t ever know what they were. I just said they were brand-name like Born or Picadillo’s. Silly me. Lol maybe I have to get a pair for my straight leg jeans.

  3. Hi Kay!
    Love the look of the jeans you’re wearing in most of the photos. The ones with the frayed hem. Could you link them please. Thank you!

  4. Perish the thought that Queen Victoria pulled off her own boots! I love straight leg jeans with Chelsea boots and a sweater. I dress like this every year regardless of what Rome or Paris are doing. It’s common sense dressing. I have one request of anything I wear. Is it comfortable and does it fit? Okay that’s two.?

  5. Thanks for the “boots ‘n’ jeans” info. I never could get a handle on an exposed ankle w/ short boots – just too cold natured, I guess! I really like the straight leg jeans on the outside. I purchased a pair of waterproof Chelsea boots recently. A great good-looking choice for rainy days!

  6. Thanks, Kay, for the clarification on pant leg width and types of boots. Most helpful.
    The Blessed for My Day message really resonated with me. I had never differentiated between serving others and serving others via God’s directions. Would you please provide an example of each to show the difference? That would be most helpful.

  7. sorry to hear you are sick. Thanks for a great post, extra impressed as you are recuperating. I am always impressed with your posts and find myself walking away with new knowledge or food for thought. Today I appreciated the different picture examples. It helps me so much to see what you are talking about. I appreciate you digging around to find all these pictures! I am inspired to go to my closet with my new info! thanks

  8. Great looks Kay! I haven’t worn any of my boots yet, but I’m looking forward to doing so. Your looks have given me other ideas, so thank you!

  9. Oh, I failed to mention that I used the link you provided to finally order the Wonder Pot set. Too many of you keep raving about them for us to remain on the sideline.

  10. Recently I purchased two pair of jeans from a company called B Sides Jeans. Love them, they are somewhere between a straight leg and a very slight bootcut. At first, I was going to have them hemmed, but after trying them on with different pairs of shoes I’ve left them as they are so.. I found all boots, mules and clogs look nice especially because the length is a little longer-top of my foot. I’ve also learned having the jean a little looser around the ankle helps with pairing shoes. After trying on nine pairs of jeans and deciding what I did and didn’t like about each I came to this conclusion. On a blog High Heels in the Wilderness, Susan joked when suggesting you need a capsule wardrobe just for jeans.

  11. Thanks, Kay! Your post was so helpful, thank you so much. I really appreciate all that you do and enjoy spending time with you in your lovely videos. I am glad you are feeling better!
    All the years we were wearing skinny jeans, I never understood how to manage the winter boots. Or the socks! Some of us always need to wear socks. Could you please link to your post that explains that? I still have some skinny jeans I will wear. I saved all my straight leg jeans from years past and just wore those in the winter. Basically, I didn’t participate in the skinny jean fashion trend at all! Thanks so much, Kay, you are a blessing and an inspiration.

  12. Hi Kay, what do you do with all the tabs on the back of Chelsea (and other) boots? Even with straight jeans at a longer length, they keep hanging on the tab when I get up and down out of my chair? I told myself yesterday that I was reserving them all for skinny jeans because I was tired of fighting with them. Oh no, ha! Also, I have boots with different shaft heights, so figuring out what pants/ jeans can be worn with them is getting hairy. I’m ready to throw up my hands, or wear them and not worry about it anymore!

    Also, I think the higher shaft boots look cute w/ cuffed jeans and socks. It might be for the younger crowd. I don’t know, though. I hope you’re feeling much better this week!

    1. Hmm. The tabs haven’t really bothered me yet on these. I do think the higher the shaft the better. I know it’s all a conundrum, especially if you still want to wear boots in your closet that have a lower shaft. In the end I think we just do the best we can and go live our lives! Ha!