You may remember a few months back that I posted about my boots dilemma and confessed that I like the trend of tucking jeans into tall boots when I see it on others, but I wasn’t sure if I could pull it off.
In those prolific comments, Big Mama offered that being fashion forward requires a little bit of risk, and my friend who posts as loonytick suggested I give it a try and to just untuck my jeans if I didn’t adjust to the look. So I took their advice and went for it. Do I know how to live on the edge, or what? Next thing you know I’ll be jumping out of airplanes and camping without a bathroom.
Any. WHO.
All it took was that first venture outside with my jeans tucked into my boots, and I have never looked back. My friends can attest that I probably wear my jeans tucked into boots 6 days out of 7. I have a myriad of cute ballet flats and high heeled ankle boots wasting away in my closet because I contemplate them for about .25 second before I opt for my Uggs.

They are so unbelievably warm and comfortable, and I’m so cold-natured that I often don’t even take them off when I get home. I can wear these all day long. And there is NOTHING like going outside in the biting cold and having my feet stay toasty warm.
I’ve had some people ask dubiously if it’s comfortable to wear my jeans tucked in, and my answer is unequivocally YES. I’ve also had some questions about how to wear the look, so here are my tips.
1) Straight or skinny jeans work best. I don’t have skinny jeans; a straight leg works just fine, and it’s also nice leg to wear with a pair of ballet flats when the weather gets warmer.
2) To keep your pants where you want them, it’s best to tuck them into a pair of socks before pulling on your boots. I have a little system where I roll up the pant leg, creating a deep cuff. Then I fold over any excess fabric on the inside of my calf and hold it in place while I pull my socks on over the jeans. Finally, I pull on my boots. They stay tucked in neatly all day long this way!
3) I feel like there should be a 3. But I think that’s it!
UPDATE: I just saw this exact topic covered on Audrey’s Mom Generations blog. I considered making a video but she did more than think about it. Check out Audrey’s video on tucking jeans into boots!
Do you have anything to add? Anything I didn’t cover? Ask me and I’ll answer in the comments!
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{ 19 comments… read them below or add one }
Adorable! Where did you find those boots?
Hello–you can’t tell us all about the look you are rockin’ and not show us a picture. Share please!
I tried it last weekend with a pair of straight leg jeans boot that I got on a super sale at 9 West after Christmas. My sister told me that I looked silly because my straight leg jeans were too baggy and kind of bunched up around my knee. I’m not really sure how to get more of the jeans in the boots so that they don’t bunch so much. Maybe I need skinny jeans. I’m not sure that I’m THAT daring though – I’m afraid that skinny jeans will look like they were painted on. Maybe the straight leg jeans will shrink in the wash…
I always wear my pants tucked in…ever since I moved to Europe. Hardly anyone here wears them the other way…
Oh lucky YOU!! Those are so cute and you are lucky you can tuck! LOL
I’m only 5’2″ and my legs are SHORT – so I feel so “dumpy” when I’ve tried that look….:-( Maybe if I’d lose 10 pounds I could try again! LOL
~Tidymom
I love those boots! I will have to say I have never tried tucking my jeans into my boots but think other people look adorable doing it. I may have to take the plunge too!
Yeah, so I where my Uggs EVERY DAY, even here in hot Houston. Ok well, maybe not all summer, but definitely even when it’s 80 degrees out…ya know they breathe and you can where them without socks and your feet don’t even get sweaty. They RAWK.
Of course hubby just told me this week they are very unsexy. That’s HIS problem, not mine.
I love the boots over jeans look too and have been to afraid. But, we had a huge snow storm here in December and I bought some rainboots from Target…totally got me used to wearing my jeans in boots. I did it to keep the bottom of my jeans from getting wet…now I want a cute pair of boots.
Love the boots…give a link to where we can find them!!
I wear my boots to and from work each day, with my pants tucked into them. It is comfy and much easier. I hate the nasty pants that drag in the muck. Yuck!
You are SUCH a joker.
You will NEVER go camping without a bathroom.
i confess i have yet to wear my jeans tucked in.
One day I hope to be as brave as you are and tuck in my jeans. Until then I think I’m going to have to wear them outside. But I agree that I couldn’t live without my Uggs!! I wear them whenever I’m not in school where they don’t really compliment my work attire.
I dig those boots. I need to get me some!
You are a gutsy one. I’d probably be the gal to screw the tucking in part up and be walking around with like a weirdo. All my jeans are boot cut too…to attempt to hide my “birthing hips” as I’ve been told. Wow, guess I just made myself sound fat…hmmm. Beth at Total Mom Haircut started a meme that I’m passing on to you (it’s all about bags). Check out Elebelly for more.
Those are some cute boots! I love that chocolate brown color!
I haven’t tried the “boots-over-jeans” style (I’m not a big risk-taker when it comes to fashion…), but I have been tempted. It looks so cozy and modern when other women wear that look.
Just one question: where are the corresponding pictures?
I’ve been totally rocking the look too. Also, I have almost the same boots, but they have the hook and loops on the side. I’m so vain, that the ones that you have ran kind of small (read: my feet are so wide) that I needed a 10!! They fit for width, but they were so long I looked like I was wearing someone else’s shoes. Mine are a bit shorter, but they are only 8s. I usually wear a 6 or 7. Stupid Uggs.
Also, let your readers know that the ones you have were (and are probably still) on sale at City Sports for $100. Mine, of course were full price. Stupid City Sports.
So sorry there was no link!! They are the Uggs Swell in Brunswick. You can google it and find best price. Lora suggests City Sports so try there! I got mine on sale at Nordstrom before Christmas.