61 Responses
Thank you for all your helpful tips styling jeans this season!! Do you have recommendations for socks if you want to intentionally show them?
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Yes, I’d like to know that as well as if you have to cuff the jeans are there anyways you like that look?
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I’m kind of over the cuffs at this point, but I won’t rule it out.
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I am a plain Jane and usually just match the color to my jeans or boots. I have these in grey and black. https://shopstyle.it/l/bMeVD
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Would love to see you do a what to wear in Nashville post with your style!
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On it! 🙂
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THANK YOU for the series on what shoe/boot goes with which jeans! So helpful! And this morning I was looking at a pair of full-length gray straight-leg jeans that I have had for years, wondering if I should cut them. I think I will wait and experiment with the length as-is first.
I haven’t yet switched out my summer for winter wardrobe yet. I’m thinking I will do shoes today and the rest this weekend. I love fall and boots are my favorite type of footwear!
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I’m excited for fall boots too!
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What a great post so us ladies can determine what to buy. Thanks, however, my budget does not allow me to spend $120 – $250 on a pair of jeans. Would love to see a post on Target or Amazon jean options that are more reasonably priced.
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Glad it’s helpful! I don’t find those brands to fit me well, but I’m sure you can find some similar styles at those retailers. 🙂
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This post was SUPER helpful! Thanks so much for doing it!
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I’m so glad!
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You do a wonderful job of keeping up with current trends. I, myself, being more than 20 years older than you have seen more trends come and go than you. Sometimes, I think that manufacturers are hood-winking us. Styles change to keep us buying and sometimes they also change to save on manufacturing costs. The current trend of unfinished, cropped hems is a good example. I think the cropped hems shorten the look of our legs. I don’t find it a good look on anyone. But, the cropped length saves money for the manufacturer and so does not putting in a hem!
The jeans you showed that are full length and brush the tops of your booties look so nice to my eye. Your legs look a mile long. I much prefer that look to any of the cropped styles. At nearly 68 i figure i can pass on certain styles that are not my cup of tea and wait a day or so, ha, ha, until the styles change to something I consider more flattering.
I wonder if i am in the minority when it comes to passing on cropped jeans styles?
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Haha! At age 65 you are speaking my language!😊
I agree about the cropped jeans. I’m 5’2” so cropped jeans make my legs even shorter. Fortunately for me I can buy cropped and they’re full length on me. I wear my jeans over my boots which is way more flattering on me!
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Agree! Short with short legs and some of these looks will not be flattering at all on me.
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62 years old here and I am wearing the cropped with booties. Proportionally, I have long legs for my 5’4” frame so I don’t feel the look chops the line much. I really like wearing the crop with my lug soled boots and a flannel shirt or cardigan. That’s my fall mainstay outfit this year.
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No matter what our age, we should pass on styles that aren’t our cup of tea. As you say, just wait 5 minutes, and a new trend will come out that you may prefer! 🙂
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This is so helpful! I appreciate all your comments. It motivated me to go through my own closet and just try things. It’s been a while sense I have been in jeans. I will make a wish list from that. Another take away for me is for me to take a picture of what works so in the morning when I am hurrying to get dressed I have a visual reminder! Your pictures have inspired me as the successes and failures pictures both learning tools. Thanks for posting all and walking us through that!
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Yeah, I do that before I travel, take pix of the outfits I can put together with what’s in my suitcase.
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Great post! Thank you for showing so many different options in lengths, brands and styles of denim. You do the work for us! Almost all my boots are low-heeled and I wish so many didn’t have the pesky “tab” on the back.
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Yeah, it’s annoying.
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I wore cropped denim this summer with fashion sneakers or sandals but will wear full length straight jeans with my booties. To my eye it looks better. And, this post confirmed that.
Thank you for doing these in depth posts. It must take a lot of time. We appreciate you!Reply
Glad it was helpful, and thank you! 🙂
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I struggle with most the boots are too high heel or the light color boots get jean dye on them if I wear them over the boots. In another couple weeks here in the NW, we will be having rain and so suede is not practical and so this season I really stopped myself from buying the lighter, suede booties. You have such good options in jeans and booties to work with. I’m retired at home, so trying to figure out booties that I will actually wear for casual and not be running around in high heels. I got excited about the lower heel Brigitte Luxe bootie you posted, but wow…..$495 is a lot. LOL I’ll keep looking. I really appreciate this post and the hard work you put into it. It really is trial and error and trying to get the right combo jeans and booties in our closets. Let us know if you know of any shoe protector that protects against Jean dye on the booties.
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Toms has some nice low-heeled boots, and the last few years Target has had some also.
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Thanks Bonnie……I’ll check Tom’s out. I do have a black heel (wedge) Tom bootie I like and is comfy. The wedge may be a little dated, but I still like them. 🙂
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I have had great success buying booties on Zulily.com (variety of brands & price points) most are returnable and another great option, at least for me is Amazon try before you buy, you can pick up to 6 pairs out, try them, pay and keep what you like, send the rest back no charge, I did this over the summer with sandals
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Great tips, Rita!
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Yeah, I know, Kathy… I got those Aquatalia boots when they were 40% off during the #NSale. I did hate to use those as an example b/c the price is out of range for many, but hopefully you get the idea how they can look with a lower heel. They are also waterproof suede. That is just about the only kind I buy. Blondo also does waterproof suede at a lower price point.
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I figured you got them on sale. 🙂 They are sooooo cute and good heel height. You look great in all the jean styles and booties. 🙂 Thanks for your hard work on your blog. It really is quality. So much information with pictures to help and great writing.
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It’s funny how a year or more ago I would have thought the longer look on jeans was boring and the cropped look was of the moment. Now I’ve gotten use to seeing the longer length and it feels more right. I bought 2 pair of suede boots with a thin (close to the leg) and higher shaft at Nordstrom several years back and they seem to be getting me through all of these transitions. Thanks for all the info that keeps us on trend!
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Isn’t it interesting how our eyes adjust? We were just talking about that in Nashville, how even the slim straight leg jeans are starting to look like skinnies to me now. It’s so funny.
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Yes, they do look like skinnies, I have to really look! I need to get some of the new styles. I know I won’t look good in any of the wider leg styles. I am going to try to find a pair of straight leg blue jeans and call it a day!
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I know I’m getting a bit ahead here, but I’m anxious to see how to style these new styles of jeans with true winter boots. Since I’m looking into buying denim *now*, it makes sense that I’m thinking ahead to winter. I just can’t see any way that winter boots are going to look good with ANYTHING but skinny! Help!!! (I’m thinking Sorel, North Face, etc)
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MMASC……I have been thinking the same thing. I want to buy more jeans, but I see Winter boots needed and I don’t know how those are going to work either. I have been trying to remember what I use to do back in the day with the longer jeans and can’t. LOL 🙂 Like you said with the Sorel or N. Face boots. I’m sure Jo-Lynne will cover this well. It again will be trial and error with trying it and getting the right combo’s in our closet. Skinnies were sooo easy.
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I’ll get there eventually! 🙂
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Looking forward when this latest round of trending passes. Dresses with ruffles and tiers, sweaters with puffs either high or low on the sleeves, and $200 plus jeans that appear worn out and are ill fitting takes the fun out of shopping for me. I love how I feel when I am well dressed in classic styles remembering the rule of thirds.
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Me too!
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Straight leg jeans are SO much easier! I’m in Texas, so boot-cut never went anywhere and that’s how I’m used to wearing jeans. Now let’s discuss the “boot cut” jeans that aren’t big enough to go over the cowgirl boots! Those drive me bonkers!
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Ooops! I was trying to say that I just opt out of the styles that don’t suit me. Like the dresses that don’t show my waist (or put it way too high). So, basically all the dresses right now except the wraps.
Rule of 1/3 is pretty important to a short girl with short legs!Reply
Yes, as we all should. 🙂
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Then you should wear classic styles and create the rule of thirds! 🙂 We should all sit out the trends that don’t work for us, while keeping an open mind to evolving styles and silhouettes.
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This may be a fashion sin, but I cut off the tab on the back my boots… so no more catching them on the hem of my jeans. Problem solved!
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That’s hilarious! I never considered that.
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Great post! It’s nice to have so many options. My boots and jeans are waiting for the weather to turn! We’ve had a nice September here in the NW. On a side note, I ordered the floral Loft tee that you are wearing in this post, last week when you told us about 50% off and free shipping. I’d been eyeing it since you posted it and the sale clinched it. Ha ha.
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Linda….I did just what you did. I bought the floral LOFT tee on the same sale and I just received it and love it. I too was holding off. As for jeans and boots, I live in the NW too and our Sept. has been wonderful, so not much need yet for boots for sure. Just got some rain today but suppose to get nice again.
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I’m so glad you love the tee! Mine should be here any day.
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Straight leg jeans are SO much easier! I’m in Texas, so boot-cut never went anywhere and that’s how I’m used to wearing jeans. Now let’s discuss the “boot cut” jeans that aren’t big enough to go over the cowgirl boots! Those drive me bonkers!
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Love the look of the AGOlDE Lana Jean. Love the NYDJ Marilyn as well. Others not so .much. My struggle is I can’t wear a heel. Need flat booties!
Thanks for your time.Reply
I have the same issue!! I’ve got knee problems and feel best when I wear flats. At least Jolynne’s blog gives us some guidance!
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I just want to say thank you so much for your guidance on jeans and shoes/boots. I’ve worn nothing but skinnies for the past few years and just bought a couple pair of straight leg jeans. I always felt a little frumpy in straight leg jeans, but with your helpful tips on shoes, I’m so much more aware of what works and what doesn’t, and I feel more pulled together!!
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I’m so glad to hear that!
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Love your tips..
I have been having a huge problem.have booties o love but having problem finding jeans to wear with them. I do not like narrow legs with them at all so looking for boot cut with just enough flare to go over them. It’s a huge problem. You didn’t mention boot cut jeans…what is your advice?Reply
Hi Edwina. This post might help: https://jolynneshane.com/what-shoes-to-wear-with-flares-this-fall.html
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I love these outfits. What did you end up doing with the socks? Did you avoid socks with the booties?
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I sometimes wear Sheec socks – these are great with booties and don’t show.
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Hi, I’m so happy I found your Blog. I’m 5’5 and have a favorite pair of lug boots. I’m struggling of where the hem should hit on the boot shaft. Also what sort of leg opening g is best for these boots . I’m 59yrs old and don’t want to look like I’m trying to be 20. I’m more of a classic dresser but definitely love fashion.
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Hey Mindy, I struggle with lug boots, to be honest. I love how my friend Dawn wore them here – I added her pic to this post: https://jolynneshane.com/how-to-wear-ankle-boots-in-the-winter.html
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Just discovered this article and it’s just what I need! Wanted to ask for help. I’m 5’10” and bought a pair of Chelsea boots here (https://patina.com/collections/womens-leather-boots/products/womens-classic-chelsea-boot?variant=41392292331717). I’m struggling to know how to pair these with jeans. I hate skinny jeans. I also struggle to find jeans long enough for me. How do I go about figuring out the inseam length I need to wear my Chelseas? I love slim, flare, and straight-leg jeans but I still can’t crack the code on this. Help!
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I would wear those with straight styles. They could be cuffed to come to the top of the boot shaft or they could fall over top. Something like this https://www.pinterest.com/pin/112730796944618713
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