Experimenting with Chelsea Boots and Straight Leg Jeans

I promised you guys I’d play around with Chelsea boots and straight leg jeans, and I’m a pleaser, so here we are!

If you’ve hung around these here parts for very long, you know that I loooove my skinny jeans. I’m still a fan, and I will continue to wear them.


Some of the newer boot styles are not playing so well with my favorite skinnies. Case in point: the Chelsea boot.

Vince Henderson boots (size 8)

What is a Chelsea Boot?

If you’re not quite sure, Chelsea boots are close-fitting, ankle-high boots with an elastic side panel, and they’re worn by both men and women.

Vince Henderson boots (size 8)

They’re a classic style that has become very much on trend as of late, and they’re quite a change from the lower shaft, western-inspired styles we’ve seen over the past few years, often with a split shaft.

I picked up these beauties at the #NSale back in August when they were on a significant markdown.

They are absolutely gorgeous, practical (waterproof… holla!) and right on trend with the Chelsea boot silhouette on a lug sole.

But now that it’s finally chilly enough around here to wear them, they have created some annoying outfit problems. As in, they don’t look very good with my go-to skinny jeans. Hmph.

Last week, I tried to wear them with these Good American Good Legs jeans I’ve been wearing so much lately, but something about the pairing just seemed off.

sweater // jeans // boots

As I explained then, these booties have a tall, slim 5″ shaft, and the jeans seem to cut off at an awkward place.

Even though they’re skinny jeans, the leg opening of the jeans appears wider than the shaft of the boot, so it chops up the line of the leg, even though it’s all the same color.

Here’s a close-up of the side view — see how the hem of the jeans gets stuck between the heel tab and my leg, and then they fall over the front of the boot.

sweater // jeans // boots

I don’t know, maybe I’m over-thinking it. It doesn’t look terrible in these pictures, but when I’m looking at myself in the mirror, it’s all I see.

And I have the same issue with other Chelsea boots too, like these Marc Fisher Yale Chelsea boots.

I think these jeans actually look worse with these boots — I guess because they have a slightly lower shaft, and the line of the leg looks even more chopped up.

sweater // jeans // boots

As we discussed in the comments of that post, Chelsea boots seem to call for a different style of jean — one with a wider leg opening that allows the jeans to fall over the boots, or a crop style with a wider leg opening.

I styled the Vince Henderson boots with the rag & bone Dre slim boyfriend jeans (currently 40% off!) for a blog post back in August, and they seem to work well together when the jeans are cuffed to land right above the shaft of the boot.

sweater (XS) // tee // jeans // boots

I wish I’d tried these yesterday during my try-on sesh, to see how they looked in the mirror. I only have photos with a side-view from that post.

Of course, that will only work when the weather is mild. Once it gets colder, I’ll want to be able to wear socks, or at least wear the jeans over the boots, so I need to see how they look left un-cuffed.

So anyway! Yesterday, I set out to experiment with Chelsea boots and straight leg jeans.

Paige Cindy Straight Ankle Jeans + Vince Henderson Chelsea Boots

This is the Paige Cindy, and it has a 27″ inseam with a 14″ leg opening, for those who pay attention to measurements.

For comparison’s sake, the off-black Good American Good Legs skinnies shown above with these same boots have a 27 1/2″ inseam with a 10″ leg opening.

sweater // jeans // boots

Don’t get too distracted by the chewed hems on these jeans. They’re giving me all the Huck Finn vibes, and I’d prefer a plan raw hem or a more traditional sewn hem for these looks, but they are the best straight ankle jeans I have to play with.

(The Paige Cindy comes in a lot of other washes with different hems, if you like the cut of the jeans and not the wash. Unfortunately, none are on sale at the moment.)

Right off the bat, I feel like this pairing works really well. The jeans have a 27″ inseam, which is the perfect ankle length on my 5’5″ frame, and they fall nicely over the boots.

They’re long enough so that they don’t chop off the leg line, but short enough to expose some of the boot, which is on trend. And let’s face it, these boots are too gorgeous to cover up!

sweater // jeans // boots

I also think the heel on the boot helps my legs look longer and leaner, even though the jeans are on the shorter side.

And finally, this solves the frozen ankle issue we all face when we wear ankle jeans with lower shaft boots that expose part of the leg.

My only issue is, the color combination on this outfit is a little harsh. The black boots create a high contrast with the lighter wash jeans, but the darker top bookends the look, so I think it works okay. I probably would not like this look with a lighter top.

Paige Straight Ankle Jeans + Marc Fisher Yale Chelsea Boots

Next, I wanted to see how the exact same outfit worked out with the lower heeled, pointy-toe Marc Fisher Chelsea boots.

Again, the color contrast is a little harsh, but I feel like the jeans and boots look okay together. For some reason, I like the chunkier Vince boots better, though.

sweater // jeans // boots

Also, these boots have a slightly lower shaft than the Vince, and the back of my jeans gets caught in them when I move around.

But also note how the way these jeans are distressed, the hem is slightly shorter in the back than in the front. If they were cut evenly all around, this might not be an issue. Or perhaps a straight leg jean with a 28″ inseam would work better with these boots.

sweater (S) // jeans (28) // target=”_blank” rel=”nofollow noopener noreferrer”boots (8)

Mother Insider Crop + Vince Henderson Chelsea Boot

Another pair of straight leg jeans that I’ve been struggling to make work with the rest of my wardrobe is these jet black Mother Insider crop jeans.

Unfortunately, this exact style is only available at Shopbop, and sizes are limited. There are more Mother Insiders at Nordstrom and Bloomies, but most have a frayed hem.

These jeans have a 25″ inseam with a 14″ leg opening, so they’re a full 2 inches shorter than the Paige Cindy shown above.

sweater (S) // jeans (28) // boots (8)

These are a true crop rather than an ankle-length jean, and I feel like they have a slightly flared silhouette, whereas the Paige Cindy definitely falls straight.

For this reason, I find these harder to style, and I always feel like they’re cutting off my leg line in an awkward way.

I’ve styled them a few times for the blog, but I rarely end up wearing them in my real life. I try them and always end up reverting to my comfort zone — skinnies.

I do like how they work with these boots. Because they are both black, there is little to no contrast between the jeans and the boots, so even though the jeans are cropped and slightly flared, I still get a cohesive look on my lower two-thirds.

sweater (S) // jeans (28) // boots (8)

The other frustration that I’ve had with the back of the jeans getting stuck on the tab of the boots is eliminated with this pairing because of the flare. It just doesn’t seem to be an issue, even though the hem of the jeans barely covers the top of the boot.

I just wish I had thought to style this outfit a bit more — I think a front tuck and a belt would really improve the overall look.

For one thing, it would balance out my proportions a bit — with the shorter jeans, a shorter top works best. Plus, it’s all rather plain, and I think a belt would really take it up a notch.

Mother Insider Crop + Marc Fisher Yale Chelsea Boot

I also wanted to see these jeans with the Marc Fisher Yale, and this is just okay to me. I don’t know if it’s the pointy toe or the shiny leather or the lower heel or a combination of all three, but something looks off to me.

sweater (S) // jeans (28) // boots (8)

Maybe the jeans and the boots are okay, and it just needs a different top. I think an edgier look on top — perhaps a moto jacket over a graphic tee — would be better suited to these boots.

I was trying to cut down on the different variables, so I styled everything with this same top, but I should have played around a bit more with other options.

sweater (S) // jeans (28) // boots (8)

The rear view is where these lose me; and I apologize for my nasty iPhone screen. I didn’t realize how bad this was until I went to upload these pix. But this rear view looks really elf-like to me, with the pointy low-heeled boots poking out from under the crop flares. I’m not feeling it.

sweater (S) // jeans (28) // boots (8)

And yes, I should have done rear view shots of the other looks… I didn’t even think about it.

Mother Insider Crop + Aquatalia Tilly

Finally, just for the sake of argument, I decided to try this same look with my Aquatalia Tilly suede sock boots.

I picked up these boots on an end of season sale last winter, and I already knew I liked how they looked with these jeans, so I wanted to try them on to compare to the Chelsea boots above. Even though they’re sold out, I link them so you can see the details and specs.

sweater (S) // jeans (28) // boots

These booties are a classic style that’s hard to define. I usually call them sock booties because of the high, slim 7″ shaft. That makes them really easy to slip under jeans and pants of all different lengths; I can even wear them under my skinnies.

They’re also weather-proof, so they’re perfect for our messy Pennsylvania winters.

The classic styling works better with this top, and in this case, I actually thought to give it a front-tuck.

sweater (S) // jeans (28) // boots

I feel like this pairing works, although I still see that skinny shaft against the wider leg of the jeans, and it seems weird to me. Maybe my eye just needs to adjust to the look after wearing primarily skinnies for so long.

Yes, I realize they aren’t Chelsea boots, but comparing other styles helps me decide if I like the Chelsea boots with these jeans or if there’s a better option.

Mother Insider Crop + AGL Pointy Toe Flats

Before I quit, I wanted to try one more thing — the AGL pointy toe flats.

Of course, these aren’t boots at all, but I had a feeling I might like them with this top and jeans, and I would love to find a few ways to wear these jeans so I can get a lower cost per wear out of them.

sweater (S) // jeans (28) // flats

While I still prefer the silhouette of a skinny jean, I can appreciate that this outfit is modern and flattering.

The proportions are working, and if I add a belt, I think I have a look I’d be comfortable wearing out and about.

sweater (S) // jeans (28) // flats

Of course, that doesn’t solve my Chelsea boot dilemma, but at least it gives me another option with these jeans.

As for the Chelsea boots, I think they work best with the straight ankle jeans.

I’m excited to come up with some other outfits around that pairing, although now I want to get a pair of straight ankle jeans without that chewed up hem… Time to go shopping, ha!

It never ends, does it!?

I hope this was fun. I know I could have been more thorough and tried some other combinations, but I wanted to get this post up today. I’ll definitely keep playing around with Chelsea boots and straight leg jeans as I’m putting outfits together over the next few weeks.

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66 Responses

  1. Oh I love those Mother jeans, I am thinking of getting those or the Mother Hustler jean. I love it paired with the loafer ! I think for your Chelsea Boot, I prefer the first look (maybe in a tad darker jean). I think since the boots are so dark, that might be what’s throwing off the look for you…..but it’s cute and modern. I love that you’re putting these looks together for us since we know your love for your skinnies. Have a great weekend.

  2. I love your Vince Henderson boots! It looked good with the rolled cuffs & not bad with the first pair of distressed black jeans. Have your tried them with black leggings? Would love to see what that looks like!

  3. I love these looks on you and appreciate this post and all the work you put into it.  I think these jeans look much more modern and flattering than the skinny jean.  Hope you get your family pics soon! 

  4. I have boots similar, I can only wear them with denim leggings, they have to fit super snug around the ankle, so that it sits right at the ankle, or I’ll pull them down over the boot-you can do this with denim leggings as they are a bit stretchy.  Regular skinny jeans, unless very fitted around the ankle, don’t work for me.

    1. Yes, I also want to try them with skinnies that fit closer to the ankle. I have one pair like that and they are cropped, so they come right to the top of the boots, but a very light wash and I didn’t like the contrast.

  5. When I saw the title of your post, I started laughing. I love my new Vince Chelsea boots (same pair– the only shoes I bought this year during the Nordy sale) but when I wanted to wear them out the other night, I tried on one pair of jeans after the other. I’ve worn Chelsea boots for 20 years, but the ones with the low heel, which have a lower shaft. Those do work with skinny jeans. I have a pair of MarcFisher snakeskin Chelsea boots that have been my go-to for 2 years. Anywho, I ended up wearing the new Chelsea boots with my R&B Dre slim jeans, which worked style-wise, but I thought the wash was too light. I tried rolling some jeans but the lighter color on the inside bothers me.
    I like the Paige Cindys the best from your photos, but Nordys seems to have mostly light washes. I’d love to find a darker wash in this style, without raw hems. Please let us know what else you find that works with the Vince Chelsea boots. When I was trying jeans on the other night, I was thinking Oh no! I spent all of this money on these boots (tried them on with shorts- lol) and now I don’t have pants to wear them with!

  6. What a fun and very informative post!  While I don’t have several pairs of boots to play with, I do have jeans with various cuts, and like you, when I put on something other than my skinnies, I struggle with finding an outfit that I like.  And I think it’s due to the cut of the jeans, that I’m not used too.  We were very blessed in middle GA to not have the wind damage that the majority of the state had, thanks to Zeta, so there weren’t as many power outages nor downed trees.  Today is sunny and so fallish with the temps.  Yay!!  Have a fabulous day!

  7. Interesting dilemma. I like the boots with the dark (light black?) skinny jeans. It’s not that I might not like another shoe better, but I like the all dark line (at least in the photos), and if it’s cold enough that you want/need the boots, then another shoe is probably impractical. I also like the look of the rolled up jeans, but again, if it’s that cold out, do you want to roll up your jeans and expose skin? I am not a fan of the paige straight jeans that go over the boots. I wouldn’t mind a lighter wash with boots, but I think I’d prefer a lighter colored boot. It also looks better to me when the bottom of the jean flares out a bit. And I like the crop flares on you (with boots or loafers), but I agree with you that I struggle with that look when I try to wear it myself.

    1. I agree – a lighter color with the Paige jeans would be ideal. I love all my taupe boots, but they don’t seem to work so well with the Paige. I need to play around and see which ones, if any, do.

  8. Me: Wow… I have everything I need for fall… bought all my favorite skinnies and even a boot cut, found jeans that actually fit my shape, loaded up on clearance shoes and boots when the stores needed me most.

    The world:  Hey look, new boots.

    Me: (Hangs head, looks at suddenly outdated closet.)

    Ugh… glad you’re here doing the heavy lifting for me, JoLynne.  Im not sure how I’ll adapt to this, but if I do, it’ll be with your guidance.  Do you think this will have staying power?

    1. Snort. You are good, I am sure! Look around and see what people around you are wearing… if you fit in, you’re fine. I am still seeing mostly skinnies around here, but I don’t live in a real fashion-forward area. I do follow tons of bloggers, though, and these looks are starting to look mainstream to me. But even among them, most still do a mix of skinnies and straight.

      I think straighter silhouettes have staying power… it’s time. Skinnies have ruled the day for a long time. But the straight crop? Not sure. Time will tell, I guess! 🙂 I feel like the ankle length is modern without looking like high waters. The crop, I dunno… I like it best with a mule or slide in the summer months.

  9. I can’t wait until these crop jeans go away. They look like your mom washed them and put them in the dryer…. I think most people seeing these pants on someone would be confused by the length. Maybe this is my over 60 age view but they’re just awful. Sorry

  10. Jo-Lynne – you are very dedicated & patient to try to make the straight jeans work with a Chelsea boot. I just can’t get excited about the look – sorry. I’m still a skinny jeans gal all the way! I love how they look & how I feel when I wear them. I’m with Lisa on the straight, cropped jeans – they look like you’ve shrunk your jeans to an odd length. And perhaps I have some history with too-short jeans as I was a very tall child & often had to wear jeans that were too short because I either couldn’t find any to fit right that were long enough or I outgrew them so quickly. Other kids can be harsh in those situations, and I still find myself having trouble being comfortable in any cropped/ ankle length jeans or pants. They look cute on others but I don’t like it on me. I do applaud you for putting together styles that are not necessarily your favorites or what you think looks good on you – that’s why you appeal to a wide audience! 

    1. Omg that’s too funny Shirley. Because I have the same experience like I don’t hate this crop straight Jean and Chelsea boot style, but my relationship with cropped jeans has probably been tarnished. Because growing up in middle school and high school , if your jeans were too short it was the most embarrassing fashion crime 😂 literally it was seen as so lame and it was frustrating for a tall girl that struggled to find jeans not only long enough but that wouldn’t shrink in the wash. This was back in the early 2000’s. I’m 32 now 😂

  11. Agreed these kind of boots looks best with straight leg or regular length bootcut jeans. Crop flare pants/jeans need to have some skin showing between the pant and foot. A heeled sandal I feel looks best with them, so I limit myself to those kinds of pants in warmer weather. Cropped wide leg jeans/pants tend to work ok with taller boots the disappear into the pant. Perhaps stick with that look instead for fall/winter. Just my thoughts. Love your looks!

    1. I do like the taller boots that disappear into the pant with these styles… the Aquatalia works really well. I wish there were more sock booties around right now… they seemed to come and go rather quickly. I don’t mean the real sock/knit styles, but the suede with that sock bootie style to them. That’s why I think I like the straight ankle better with the Vince Henderson than the crop straight. I don’t want them to just meet, they need to show some skin, or cover the boot.

  12. I appreciate you doing the heavy lifting for us. I thought you looked great in all the looks, with the exception of the back view “elf” look. I see what you are saying there, and that’s a reminder to us all to check the back view, always. I bought a pair of crop flares in a very light wash that I wore with sandals in warmer weather. But now that I think about it, I don’t think I could bring myself to try them with a taller shaft boot. I think it looks good on you, but I can’t picture it looking right on me, and I think that’s how it is with you and most of us. It’s hard to get out of our comfort zones. I really don’t see this look lasting for long, really, so right now I think I won’t even try it. If it starts becoming mainstream, it will look more normal to us and maybe easier to pull off. I appreciate your persistence and your position as a fashion blogger to try to make them work. 

  13. Well, I know that you are not really a fan, but I am thinking these boots would look best with bootcut jeans. the boot will not be seen, which I know kind of defeats the purpose of wearing the higher boot, but ………
    or, the straight jeans work, too.

  14. Great post!  I love a cropped straight or flare with a flat or wedge in the milder weather, but for winter…Chelsea boots and full length bootcut jeans are a match made in heaven!  It’s what I’m wearing right now!

  15. I think the Chelsea boot looks best with straight leg cuffed jean that you styled earlier. I think I just don’t like the pointed toe Chelsea. I think of elf too so distracts from the outfit etc. Is it to late to return them? I just don’t see you grabbing them and wearing them if so much work to style them. Unless you keep them for midi skirt with tights? I don’t like them at all with the flare jean. I’m not into flare crop but they do look good with the pointed toe flats. So worth keeping for those. I just think it’s been hard to embrace the new jean styles. Skinnies are just so easy. Hope you find a day for family photos. I remember those days, trying to get 3 kids schedules to mesh. Have a good weekend. Today is our only day of rain then back to clearing later and sunny 60’s for  weekend. We had sun all week. We’ve had great late Fall weather for NW Oregon.  

    1. I’ve struggled with the pointy toe boots ever since I got them. I can’t return, but I may not keep forever. For now, they’re nice to have to experiment with. And I did go ahead and wear them the other night to Oktoberfest with the Good American skinnies. I just told myself I was overthinking it, and I wore them. They’re nice b/c they’re comfortable, and the low heel is better for casual gatherings. Most of my booties are higher and I feel silly wearing them to a friend’s outdoor party, lol. Now, the Vince I would have worn, b/c the lug sole makes them casual. I wanted to wear them that night. I think I need an off-black straight ankle jean.

  16. I preferred them paired with the cuffed boyfriend jeans. I love cropped pants in the warmer months paired with sandals or fashion sneakers. I’ve played with them with booties but I’m just not feeling it. Why do some women pull it off so easily? 

    1. I think they’re taller… do you follow Fashion Jackson? Hers always come to the top of the bootie, and even expose some skin. But she is 5’10” and has legs for days. 🙂

  17. PS. I have same problem when I want to wear my Chelsea style rubber rain boots. The skinny Jeans get stuck in the back pull on tab. I find I have to cuff jean high enough and then cuts leg line off. But I don’t over think it as I even wear socks to stay warm. I figure it’s raining and I’m usually bundled up etc. 🙂 

  18. When Kelly @ AYW showed the Chelsea boot a few weeks ago in her FB Live, I immediately thought those are going to be hard to wear. The boots with a short shaft are so easy to wear with ankle-length or cropped jeans.

  19. Your penchant for the crop length of jeans is not appealing. The only picture I saw that I would wear is the blue jean with the chewed hem that covered the back of the boot.

  20. Thanks for the timely post and all the work putting it together. Now with cooler weather I will be wearing my boots and with all the different shaft sizes and pant lengths it becoming confusing. This post is very

  21. Love this post of you experimenting with the Chelsea boots and jeans. Almost like we’re all sitting in your bedroom together as you try the different combinations. My favorite comment that had me laughing out loud – the “elf-look” – you nailed it!!! 😀

    Thanks for all your thoughtful, conscientious, and honest efforts – you’re the best!

  22. That was fun to read. Check out R&B Nina (high rise) cigarette 27 in inseam, 14 in opening. They are my go to for heeled chelsea boot and occasionally combat. Black is on super sale right now.

  23. The boots with the Paige Cindy’s was my favorite look.  So modern!  Loved it.  I do agree a darker wash would be a bit better.  I know you are always (?) looking for new blog material that interest your followers….I would love to see suggestions on tops/sweaters to wear during Zooming, FaceTime teleconferencing whatever.  I am doing that so often many these days.  Thanks for such a fun blog..

  24. I only like shorter jeans in warm weather when I can wear sandals or shoes without socks. And even in warm weather I need to be careful that shorter pants/jeans don’t look like “high-water” pants that shrunk…..better then to go with an actual crop than look like I out-grew my pants.  Warm weather is long gone and we are into “wear the darned socks to keep your ankles warm” weather. Once we get to Fall and then Winter pants of any kind need to sit over the boot the way any Tailor will hem your pants. Look is Classic and always works no matter what weird and wonderful “new” thing is “in”.

  25. Your post totally explained why I’ve struggled for the past 2-3 years trying to find a pair of this boot style that I like.  I’ve probably returned 10 pair to Nordstrom in that time. As an over 60 retiree my jean style is straight and sometimes slight bootcut. I can’t make myself wear short/crop pants since as a girl my pants were always too short for my very long legs. This post was so helpful and now I will focus on a shorter shaft boot or stick with bootcut jeans when I wear boots. 

    1. If you wear a more traditional length straight and bootcut, I think more classic styles of bootie look best – slimmer, sleeker cuts that you can wear under the jeans. Did you see the Talbots ones I styled last week? I wore them with skinnies but I think they would look great with a full length straight or bootcut. https://shopstyle.it/l/bnW2q

  26. LOVE the Mother Crop jeans! Think they look perfect with the Vince Chelsea boots! 😍 I would wear the heck out of those jeans! Haha! Also love them with the Aquatailia Tillly’s and the Agl flats. Can’t go wrong with those combos.  

  27. I like them best with the cropped boyfriend jeans with the raw cuffed hem.  The flare leg crops look like highwaters 🙈

  28. JoLynne,  I’ve never found another blogger who’s so willing to put themselves out there showing the good, the bad, and the ugly. No matter what though, you always look pretty. I think the problem with the crop jeans is the length on you. They seem to be a tad bit too long. I opened the link to the Mother black crops and on the models they’re all a good inch shorter.  I noticed while shopping at Whole Foods yesterday quite a few women wearing straight crops. Of course since I’m in So CA and it’s been in the low 80s people are wearing them with tees and sandals or mules. But they all looked really fresh and current. I felt a little dated in my distressed skinny jeans! I have no good advice on the Chelsea boots; not a fan on me as they’re too clunky on my body type. My son’s girlfriend wears them though with boho style midi dresses and boyfriend jeans with a rolled cuff. 

    1. Yeah, I’ve often felt I’m about an inch or two too short to pull off the look well. And I have always liked them best with mules and and slides. That’s why the boots are confounding me. I liked them better with the sock bootie styles, and they are more sleek and elegant in nature, whereas the Chelsea is a bit rugged. I wonder why the sock booties didn’t stick around for long.

  29. I appreciate all of your hard work on this topic. I’ve tried really hard to let my eyes adjust to the crop straights, the crop flares, and all of the other new denim styles that are supposed to be pushing skinnies out of the spotlight, but I just don’t like any of them. I truly believe that in a couple of years from now, we will be looking back at these denim trends and wondering why we ever thought pants that looked like they had been severely shrunken in the wash or looked like they should have been used to adorn a scarecrow were a good style choice. The fact that it is so difficult to pick exactly the right pair of boots or shoes for each pair of jeans just underscores how these styles won’t last. Many people don’t have enough time and money to invest in all the boots needed to style all the denim options, let alone enough patience to match everything up. Too much frustration and not enough fun. Thanks again for shedding light on this dilemma, but I don’t want to feel the same emotions getting dressed each morning that I used to experience when trying to do my algebra homework back in the day.

    1. I hear ya, Rhonda, and we might. But the funny thing is, I remember people being this confounded by skinny jeans and ankle boots a few years ago. That’s why I wrote the post on “how to wear ankle boots” like 5 years ago, and it was sooo popular and got traffic from Pinterest and Google for years. I’ve since updated it to include other styles of pants, but it was all about pairing skinny jeans and ankle boots and the different combinations. Now, they seem so easy, but they weren’t at first. So yeah, I don’t necessarily think this is that different… or it may be a passing fad. I don’t feel as modern with full length straight jeans and bootcuts, so I will continue playing around with these, as well as wearing my beloved skinnies. 🙂 (Oh, and I find this fun… ha! I’m weird like that.)

  30. My question is, how do theses shorter, 25-27”, Jean do while sitting. One would think they draw up and expose a lot of skin…looking rather awkward. 

    1. I actually sat down in each of these looks, to see how it looks and to see how they fell when I stood back up. 🙂 They don’t look weird to me. Also, you can wear black knee socks, if you don’t want your skin to show, or for warmth..

  31. New here!  LOVED this post.  Laughed because I spent part of yesterday looking for a pair of straight or slim boyfriend jeans.  Have been reaching for the only pair I have (7ForAllMankind relaxed skinnies) too much.  They are distressed which I am not always in the mood for.  The pair I almost bought had a slight flare, and I really don’t want that.  I’m 5’3″ and tiny and I think it just makes my legs look shorter.  Also, I’m 61 and it starts to get into “old lady capri” territory.  LOL.  Thanks for all the try ons.  I’m going to be watching for other posts that feature “not skinny” jeans.  Good luck with the photo and weather!

  32. You clearly want to like the Marc Fisher boots but you don’t 😉. You (and  I)  love the Vince Henderson boots

    On a side note, thank you for your blog.  We have the same body type and style, and you’ve helped me realize that I was wearing my tops too big which had the opposite effect of not accentuating being larger on top. 

  33.  I’m having exactly the same struggle, having a hard time styling the straight legs, though I’m ready for a change!  I realize these aren’t “real” problems, but it’s a fun diversion and I want to look current.  Thanks for your fun and informative content!

  34. I love your blog! So what is the best look? I only have skinny jeans and a couple of cute boots that I don’t wear because they don’t look right. I bought some booties, but would love to make my ankle boots work!

  35. So I practically live in black skinny jeans and Chelsea boots in the winter. I have some that have a shorter shaft and fit reasonably close on the ankle. I wear them with black socks and roll whatever jeans I’m wearing so they hit exactly at the top of the boot but not cover it. Here’s a visual example: https://www.pinterest.com/pin/1548181132185938/.

    1. See, that looks perfect to me. But there must be an issue with the length of my jeans because it never works out for me. I tried cuffing skinny jeans with mine and that looked bad too. The Vince have a much different shape and shaft height than your picture but the Marc Fisher should work like that. I do wear those with my skinnies but they always look awkward to me.

  36. Cute boots!  Everything I see with Chelsea boots is either very skinny pants or a dress.  I was looking at your 10-31 post.  Have you tried them with your jeggings?  Also, they do seem to go best with black or dark jeans,; however, you might think this is nuts, but I think they would be cool with your white jeans and a chunky black sweater.  

  37. Hi Jo-Lynne, Yes, I’ve been struggling with the same conundrum! I am 5ft 4 and cannot wear ankle boots with heels so this is even more limiting! I think I have finally worked out how to wear my pointy toe higher shaft, slim fitting Chelsea/Western style boot! My final conclusion and solution has been to cut some black slim fit jeans so they end quite high ( I initially thought eeeks!) leaving a small gap of skin showing between the bottom of the jean and the top of the boot. I think the raw edge helps and the slightly wider opening helps. I think the jeans work best if they are highish waisted and one needs to either front tuck or have a fairly short top e.g. jumper with welt. I followed your instructions on cutting jeans and was very pleased with the result and you were right, they do fray after a wash! Thanks for the time and effort you put into all your posts! Dawn

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