How To Style Ankle Boots With Loose Jeans / When To Cuff Or Roll The Hem / Fall 2021 What To Wear

[@Howiesgirl]

It's funny how styles have changed through the years. Back when I was younger & more concerned with style than comfort, no one would have been caught dead with our jeans being so short that you could see skin between the bottom of our jeans & the top of our boots. Generally all jeans had to be long enough to touch the top of the foot. Anything shorter were jokingly called "floods"-- as in you could wear them during a flood without getting them wet. Unfortunately, due to health issues, I don't get to wear many cute shoes these days. No pointed toes or heels for me😥. I very much enjoyed this video, even though it doesn't really apply to me. I like to see what younger people are wearing, & what's considered fashionable now, 30 years after my heyday.

[@YourGuideToStyle]

I love your thoughts and thank you so much for watching! I am glad you enjoyed the video!

[@jeansmith5668]

I remember floods from high school! Your ankles are having a party, invite your pants down!

[@clwm2dlw]

That's probably why I can't get into this trend. I think it looks terrible with skin showing.

[@dianaragub-schwartz4416]

so true. In the Philippines, we call them "baha" which means flood. People wouldlaugh at you and ask you to stop wearing your baby clothes. lmao!

[@debrazawlocki3975]

Right?

[@lose999]

The high heel/ shaft black boots are #1 for all these looks.

[@michelecampbell568]

I can tell there was a lot of work put into this video. Thanks for the very thorough lookbook.

[@YourGuideToStyle]

Thank you so much for saying that! I'm glad you enjoyed it! 💖

[@pajamamama5965]

I really appreciate this video. As an overweight hourglass with heavy hips and thighs but skinny calves, I really prefer the bootcut and wide leg, but also a slim straight can work if I have a tunic length blouse or sweater. I'm so relieved to have options other than a skinny, because I find them uncomfortable but they also make me look ridiculous LOL. I know a lot of people like them and look good in them. If I want a comfortable casual look, I prefer a dressy black legging with knee-high black flat boots to match. So slimming yet forever stylish.

[@YourGuideToStyle]

I am so glad you loved this! I have a wide leg styling video coming soon!

[@purplehound2420]

Thank you for this video. It made me realize that I hate the flood look that was the majority of these styles so I know know to skip those cuts. They make the leg look super short and with a long torso, that is the last thing I'd want. Please keep doing these types of videos. Thank you!

[@YourGuideToStyle]

I totally agree! You are welcome!

[@moiraeve1]

@@YourGuideToStyle Purple Hound is right. People are usually short torso, long leg, OR long torso, short leg. The rare person is perfectly proportioned--they're lucky!

[@mkim4091]

I also have a long torso and short legs although I'm 5'7. High waist tapered jeans elongate my legs. Also tucking in shirt in monocrhrome outfit balances me.

[@cambriavictory]

back in the 90's if it was summer, we all wore flip flops with our boot cuts!

[@YourGuideToStyle]

Yes we did and they would drag on the ground lol!

[@marilynhuffaker8915]

Thank you so much for not trying to *sell* me jeans or booties! Your comments are right on point. My favorite styles are not cuffed, especially with those sock booties. Two thumbs up!!

[@YourGuideToStyle]

Thank you Marilyn! I like styles best not cuffed as well!

[@karenrader2160]

Am I the only person here who thinks trying to get these combinations right is more trouble than it's worth? Life is hard enough..Love your videos Jamie. This is just all too much for my 54 year old self.

[@YourGuideToStyle]

Haha trying to save you the trouble! 😃

[@karenrader2160]

@@YourGuideToStyle Thank you😟

[@debrazawlocki3975]

Thank you. The choice of bootie with jean hemline is a painful timewaster. I have come to the realization it's easier to first buy boots, then buy jeans to go with them rather than figure out the parings with jeans on hand.

[@lisabailey6605]

The black sock bootie looks good with everything

[@YourGuideToStyle]

Yes they do!

[@jenflanaganyt]

This is EXTREMELY helpful. So many thanks!

[@emilypasold7767]

love your channel. This really helped me about what to wear with my boots as far as jeans love love ❤️

[@YourGuideToStyle]

Thank you and I am glad it was helpful!

[@debragregory3539]

Informative thanks. I’m old school and still following the ‘match the colour of the footwear with the bottoms’ advice for shorty gals but I’ll give your advice a go. Oh and I’m taking the fireplace decor too.👍🏻

[@YourGuideToStyle]

I think that's great. It a good way to make you look a little taller. I appreciate you giving some of these a try and thanks on the fireplace decor!

[@Dabonbonsings]

I cuff my vintage loose straight jean with lug sole Chelsea boots. It gives edge and balance. I also wear a patterned sock with it since I generally don’t wear prints.

[@YourGuideToStyle]

That sounds like it would be a really cute look Bonnie! Thanks for letting us know!

[@aminakhnifi7454]

Well done. Bravo and thanks so much. I have seen a lot of vidéos about styling jeans and boots but your video is the best .(J'ai bien mémorisé avec vos exemples les détails)

[@YourGuideToStyle]

Wow, thank you!

[@marietterasmussen9692]

Very helpful. Thank you for all the work you put into creating this content. ❤

[@YourGuideToStyle]

You are so welcome!

[@cg50621Q]

So helpful. Thank you. Wish I had seen this earlier. My key takeaway was that the medium shaft boots are fairly challenging.

[@YourGuideToStyle]

Thank you! With the new styles they definitely are!

[@angelamelum4304]

This video was so very helpful. Saving it for future reference.

[@YourGuideToStyle]

Yay! I am so glad! Thanks!

[@sock_account]

This was a masterclass, thank you!

[@YourGuideToStyle]

You are welcome!

[@meditationgodsway1834]

I have to say that I don't like any of these jeans so I don't think I'll be going with this trend, they all look sloppy to me. It's just not my style. That being said it seemed that if you're going to buy some new booties, the sock booties were the preferred ones for all the jeans. Great video!

[@YourGuideToStyle]

Hi Pamela! They are not for everyone and I still prefer my skinny jeans over these styles any day! Yes, the sock booties were definitely the best and went with every single style!

[@cyndysuz]

Love this! Great fashion advice for normal gals who want to look stylish but not kooky….glad I found you! Thanks….looking forward to more💃

[@YourGuideToStyle]

Thank you Cynthia! I am so glad it was helpful!

[@kyleguersey5004]

Q&A. Please tell me why most brands (Loft/Talbots) has the majority of their pants in cropped! I have short legs and I also have an aversion to cropped anything! I think it generally is unflattering because it makes your legs look shorter! I am older maybe thats why (64) but I’m also an inverted triangle and cropped rarely looks good on me except in summer with a 2” sandal.

[@karenrader2160]

I totally agree!

[@tracybelnap124]

I was so happy to find you. I bought all these jeans and boots and just struggled to make them work. Very helpful.

[@YourGuideToStyle]

Hi Tracy! I am glad you found me too! So glad to have helped you!

[@christinajohnson739]

@@YourGuideToStyle Not who you replied to, but I wanted to respond to one of your comments because I had a question and I hoped you would see it. I’m mostly deaf and KZbin really messes the closed captions up, so I couldn’t watch your video. But it seems to have good info based on the comments :) I was hoping you could help- I have some chunky 2” heeled black Chelsea boots that I love. I bought a pair of faded black Abercrombie ultra-high waisted 90’s straight jeans to go with them. The hem falls to the top of the boot, kind of in the zone where a boot cut hem would fall. Should I just wear like that or should I cuff them? I’m hesitant to cuff because I’m short and feel it would break up my vertical line? But I’m also not used to straight leg jeans so idk what to do here lol Thank you for any help!

[@amritasingh6644]

Thank you! You legitimized the struggle I’m having with my cute new white low shaft booties and the hem of my jeans. It’s just not gonna work and I’ll have to return them unless I can find another use.

[@YourGuideToStyle]

What style jeans do you like to wear? A white low shaft should be a fun option to wear with lots of ankle styles.

[@juleannedawson9287]

Lots of great information. The images were perfect and really showed us the looks. Nice job!

[@YourGuideToStyle]

Thank you Juleanne!

[@gailbrack940]

QA: I wear bootcut jeans and pants and I believe that the flare leg jean rules apply. I am uncomfortable showing skin when I sit down or cross my legs. Are trouser socks okay?

[@oliviajoneslife]

Awesome video! Definitely picking up a sock bootie now, they seem to go with everything!

[@lindagillespie6556]

It's strange, I just didn't quite agree with any of your choices, esp the combat boots, you should have tucked in the skinny and distressed both, but I appreciated the fact that you made a video and shared your ideas, so thank you!

[@YourGuideToStyle]

I am okay with that. I did not have any skinny jean styles in this video. I have a video on skinny jeans styles and I did tuck them into some of the booties!

[@sandratrent270]

What about a skinny jean? I know they are out of style; but admit that they are still my favorite!. thanks.

[@YourGuideToStyle]

I have a video on that! kzbin.info/www/bejne/aJKXiGqhq7WsnKc They are still my favorite as well!

[@jeaniepritchard4444]

Thank you for this video!! Lots of good information. I think I like the last pair the best. I am 5'5" or 5'4.5". Slightly too tall for petite, so ankle jeans can look longer on me. So glad I found your channel. All of your videos are so helpful.

[@YourGuideToStyle]

Thank you Jeanie! I love the last pair too! I am the same height, 5'4. Ankle usually is longer on me as well but I have found a couple that work okay, like the one in the video. If you look for cropped versions like the Levi's I have on they would work great for you!

[@dianariglet4257]

Super helpful video! Thank you! Plus you made choosing the right bootie for your jeans easy-my take away, there needs to be a sliver of skin or tight showing between jean and bootie. How would you style a mid-calf (slouchy or slightly wide slightly wide shaft or tall boot? I may splurge on a pair of Isabel Marants,

[@YourGuideToStyle]

Hi Diana! I would just tuck in the jeans with the mid-calf slouchy and tall boots! I bet the Isabel Marant's are amazing and I say go for it!

[@dianariglet4257]

@@YourGuideToStyle Yes! That feels right. I'm thinking straight, not necessarily skinny for a fressher look.The Isabel Marants are an investment. I know a French influencer who still has her 18 year old Bally's. They are a classic and it's so fun to see ho she style's them. Looking forward to more videos from you girl. thank you!

[@connieodonnell1344]

Enjoyed your video. Your information was quite helpful. Winters in Canada can get quite frigid so what do you suggest I wear on my legs when I don’t want to show bare skin?

[@YourGuideToStyle]

That's a tough one and I get that question a lot. If it's super cold than I would try to find a taller and skinny shaft ankle boot to go under the leg to keep your legs covered.

[@sassysenior6116]

For my two cents worth, I like all the jeans that worked with the sock booty the best. Now I have to look for a sock booty!

[@YourGuideToStyle]

Me too!

[@trishac9516]

Just found your channel and I love this video! I am barely 5ft 2in and I have a couple of cropped semi/-flare pants, not jeans, but a kind of ponte-knit. One pair is black and the other is a grey / black plaid. I would like to wear them with medium shaft black booties. My question is, should I use the rules that you have for jeans or can I have a little skin showing? Thank you 😚

[@YourGuideToStyle]

Hi Trisha! I am glad you found this helpful! I think and hope on the ones without a skinny shaft I said to show a little skin especially if it is cropped so you are on the right track! You can do the same with pants! Thanks for watching!

[@carmenmichaelian8307]

I enjoyed watching your video. I have a nice pair of medium size 6 inch boots. I usually wear my pants and jeans over them. What do you suggest?

[@YourGuideToStyle]

Hi Carmen, if the jeans go over them nicely and don't hug the shaft or get caught in the shaft than you are good! Are the shafts of your ankle boots skinny or wider?

[@carmenmichaelian8307]

@@YourGuideToStyle they are skinny but not too tight.

[@YourGuideToStyle]

Okay. I think that would work fine with wearing them over the shaft as long as the leg opening is loose over them.

[@sheilakosoff5806]

Great video! So informative. I would love more if these jeans styling video. I just added jeans to my wardrobe since I have a more casual style and only wear booties or boots from September to April. Thank you for the tips and visuals that explained everything so well.

[@YourGuideToStyle]

Thank you! And you are so welcome Sheila!

[@kellyrashedi2303]

Very helpful for this 57 year old!

[@YourGuideToStyle]

Thank you and I am so glad!

[@jls6063]

This video was extremely helpful!!

[@YourGuideToStyle]

I'm so glad! Thank you!

[@julielivinlife2447]

I appreciate this so much. I just got a pair of booties this year that I love . So this helps me to know how to wear them (much needed help).

[@YourGuideToStyle]

Thanks Julie! Glad it was helpful!

[@susansisk829]

Wow…lots of food for thought here which does provide clarity. This was immensely helpful. Would I wear any shaft height with leggings or do I still want skin to show? Thank you very much!

[@YourGuideToStyle]

With leggings I think you can wear any shaft height you prefer. Personally, I don't think you have to show skin unless you want to!

[@missjenny1953]

Mom jeans with combat boots. 👍

[@Mxtraveler]

Great tips!

[@YourGuideToStyle]

Thank you!

[@camiscloset2369]

I'm not even sure what a "Mom" jean is. Honestly, I don't think I want to know. I'm 54 and I wore those hideous high waisted jeans in high school and I swore I'd never wear them again. 30 years later, they are just as uncomfortable as they were back then. I don't like pants that hold up my boobs. They remind me of Fred Mertz's pants if you are old enough to know who I'm referring to, lol. With that being said, the photo of the mom jeans with your boots just don't work. Looks too frumpy. I cant pull that off because I'm only 5'1" and thin. I need fitted jeans and tapered legs with boots unless they are flare leg and then I wear a boot under it. Great video though. I enjoyed it.

[@YourGuideToStyle]

Ya, the "mom" jean is a term that is overused if you ask me. They are usually really high waisted and have a tapered leg. But you can also find them with a straight leg. Most jeans given this name I have not liked but I did like the loose distressed version I had on because it was actually comfortable. The looser styles can look frumpy if you are not careful but I thought that pair actually work well for me but I know not everyone would agree. I am glad you know what works well for you and thank you for watching my video! I am glad you enjoyed it!

[@sassysenior6116]

Can you suggest where I might find a pointy toe sock bootie with the higher shaft? A lot I looked at didn't indicate shaft height; except for 1! And I don't have wide feet....I have narrow .....

[@YourGuideToStyle]

Hi! I found a pair but there are only a few left. It doesn't give the shaft height but it's definitely looks 6 to 8 inches high. rstyle.me/+j0dOW9ewoNmr0A_lnOMU1g I also linked some others in the description but none of them were pointed toe. These are cute and a higher shaft but square toe: rstyle.me/+eA9i77aMODE1Nx_Th9sL-w These have a 6 inch shaft and a high heel: rstyle.me/+Vdwz5njr7bJkErxloCa3xw

[@joannehutt7120]

My fave look was with the sock booties for sure. I recently purchased low and medium shaft booties and have found it difficult to style the medium. Id love to see this done with leggings and the bootie styles. Thank you for the great info, I mat just have to invest in a pair of sock booties. Any brand you recommend?

[@YourGuideToStyle]

The sock booties went with every single style I tried on, so this was my favorite as well. Thanks for letting me know you want a video on leggings and booties because I have had others suggest that as well. I think a good price range and decent quality would be Steve Madden and I think I linked some below of his. I also like Sam Edelman and there was a great looking pair by Everlane that I also linked below.

[@DANCINGDREAMNYC]

How about wide leg jeans? What booties with wide leg jeans? If any?

[@YourGuideToStyle]

Great question! I did not do wide legs in this video because I did not have any! But I think it would look best if you followed the same suggestions for them as you would the flare leg. Just something that has an extended toe and a heel so the wide leg end up an inch or so off the floor and the shaft I don't think matters because the leg opening goes over it.

[@laurasudderth2060]

I am 5’2” and I have a pair of straight jeans that are longer than my ankle . I want to know if I can wear over the shaft of my pointy boots?

[@YourGuideToStyle]

Absolutely! 👍

[@janeenwilliams2868]

Great info ! Thank you

[@YourGuideToStyle]

Glad it was helpful! Thank you Janeen!

[@relinhatropicana4237]

Thank you a lot for this great video !

[@YourGuideToStyle]

You are welcome! Thank you!

[@jillkent6134]

Would this also apply to smart cuffed joggers ? I have several pairs and need to know what boots or shoes to go with them, ps I have to fold and cuff 3 times to shoe ankle.

[@YourGuideToStyle]

Hi Jill! Thanks for asking that question. I would recommend you not rolling them up. You will lose the look of the joggers if you do that. I like joggers best as a sportier look so you could do fashion or athletic sneakers, even high top sneakers if they don't get too slouchy. You could also do casual flats like a loafer with a slightly chunkier sole than a regular dress loafer. If you could find a pair of joggers that came a couple of inches above the ankle than a casual ankle boot would work but only if you didn't have to roll them up. I will have a video coming this week that will include joggers and ankle boots.

[@myozbubble]

Great info and tips! TFS!

[@YourGuideToStyle]

Thanks so much!

[@barbschening9159]

Good info but what about showing boots with skinny jeans?

[@YourGuideToStyle]

Thank you Barb! I am planning on doing that one here soon. I wanted to do the loose jeans since it seemed like so many people were unsure of how to style these new trends. Thanks for watching!

[@barbschening9159]

Thanks!

[@prayonkreutz2398]

The Loose Vintage Jeans needed to be longer. You can also pin tuck cuff the straight leg jeans too (80s cuff).

[@YourGuideToStyle]

Thanks for you input!

[@moiraeve1]

I think I understand the underlying principle now--to allow people to see the definition of your ankle under the boots/shoes/pants.

[@YourGuideToStyle]

It definitely looks better unless you have the really skinny shaft ankle boots on that can go underneath the leg openings.

[@seattlegirl2077]

I think the skin looks terrible unless it is summer and then you should wear flats

[@valorieyoung8805]

I am 4’11 is cuffing straight leg gonna make me look shorter

[@YourGuideToStyle]

I think it depends on how large the cuff ends up being. But if you wore a shoe that has some sort of heel (doesn't have to be high) to give a little bit more height to you it could work. I do think that it might be better if you could find a pair in a petite cut that was the right length or just hem them.

[@chellejack3480]

I have really thick ankles and they're not my best feature, so I never want to wear anything that shows my ankles.

[@YourGuideToStyle]

I understand! Thanks for your feedback!

[@michelebrotman5345]

You forgot to style wide leg jeans which I love.

[@YourGuideToStyle]

Hi Michele! I did not forget! I actually didn't have a pair at the time to style them for you guys. I looked but didn't find any that worked for me. I think you can apply the same suggestions for the flare legs to a wide leg that is full length.

[@bonniebenz8792]

I wish you would of showed leggings with the boots. I only wear those or very slim leg pants and jeggings

[@YourGuideToStyle]

Hi Bonnie, I was targeting looser styles in this one which is why I didn't talk about leggings. That might be a good idea for another video though.

[@laurasudderth2060]

Let me add to my question. The jeans actually don’t show much of the shaft.

[@ella8874]

Soooo helpful, I liked all of the looks!!!

[@mkim4091]

Tapered leg elongates the legs. Your legs looked long in them but not balloon taper.

[@YourGuideToStyle]

Ya, I am not a fan of the balloon taper!

[@shelia12047]

I'll be happy to see this trend pass. It's not flattering to anyone in my opinion. It makes the leg look short, which makes the body look wider. I think the higher shaft boot is the only one that's flattering to the style..

[@YourGuideToStyle]

Ya, I think I would like it to pass as well. I love my skinny jeans the best still.

[@lapetitepoire5]

Showing all these boots worn barefoot is a bit unrealistic, especially in fall/winter/spring. I feel like a better depiction would have shown all these jeans with socks, which most of them look silly with most footwear. Skinnies (that can tuck into boots) or boot leg / straight leg (that go over the bootie but down to the heel) are much more practical. Cropped or ankle-length jeans have very limited use in cooler climates, and in the few months a year when it's hot outside, it's generally too hot for jeans and boots anyway.

[@YourGuideToStyle]

Thanks for your thoughts. I was wearing low profile socks and purposed for you to not be able to see them. I offered many options like the sock booties that can be worn underneath the leg of the jeans if you did not like wearing these in cooler weather. I have a video on skinny jeans as well that talks about tucking them in the booties.

[@bethknight4436]

I think that all the boots that are shown are designed to wear with skinny jeans.

[@pbear7814]

I like a lot of these, but the balloon pants don’t look good with any boot.

[@YourGuideToStyle]

I know, they are a struggle!

[@lizradi5316]

Great video! I learned allot on what to wear my booties with. Now I won't embarrass my children when I am out and about!

[@YourGuideToStyle]

Lol! Thanks Liz!

[@dianeberlin5969]

Hate the look of "floods" pants

[@dianaragub-schwartz4416]

I think we have to consider your height too. If you cuff these jeans, anyone who has short legs can look stunted.

[@michellebilodeau3882]

This style with the skin showing above boots is goofy looking. Ugh...no way.

[@YourGuideToStyle]

Lol, that's okay if you don't like it! :)

[@KelLAkiwi]

I think loafers or chunky shoes are better with these styles of jeans, rather than the booties, which are better with skinnys

[@YourGuideToStyle]

Thanks for you thoughts. I do agree that those styles look great with these looser jeans.

[@jo-annmaruszak9885]

Gla

[@fhol]

Balloon leg jeans are a no go for me, the association that comes up is ‘barrel’, and that’s not a look I want to have.

[@YourGuideToStyle]

I totally agree with you! I don't love them but I know some people do!

[@christine-xn1jr]

Can I say that I have been watching some of these transports you created? And live for it. I really like the amount of information you provide in the reviews of each product, I have to buy some products after watching your video amzrepz.com

[@i2harry]

Rather confusing with so many combinations…

[@lindsayslifecafe7569]

All of these jeans are terrible 🙈. The only Jean that looks good every time is the skinny.

[@YourGuideToStyle]

I do agree that skinny jeans are much easier to wear!