Oh man! It’s getting chill-tastic in Austin!
And by chill-tastic, I of course mean it’s 55ºF. Cold weather pansies unite!
You know how puppies get a little wild and frisky when it starts getting cold outside? You let them into the backyard and they just tear across the yard + roll around in leaves, all the while sporting that happy puppy face? That’s how I’m feeling these days. (Yup. Just compared myself to a puppy.) All energized + frisky about the cold weather.
Sidenote — I just looked up frisky on thesaurus.com and some of the synonyms are too hilarious not to share:
Zesty. Coltish. Feeling one’s oats. Frolicsome. Larkish.
And my personal favorite:
Full of beans.
True story. I did not make this up. I am apparently feeling full of beans right now. Where are those laughing-so-hard-you’re-crying emojis when you need them?!
Ahem. We’ve gotten way off topic here.
SO it’s been chilly in Austin + I’m looking for ways to layer on the warmth. I love ankle boots — I actually never wear tall boots anymore — but sometimes ankle boots just need a little extra warmth. And while, yes, I prefer to go sockless, sometimes a girl just needs a cozy pair of socks.
So I’ve been experimenting with socks + ankle boots. And I’ve settled on the way I’ll be wearing my socks + ankle boots this fall/winter: Rolled jeans + tucked socks.
Here’s how to do it:
1. Give your jeans two little rolls.
2. Slip on your socks + bunch them up + tuck them under your jeans
3. Slip your ankle booties on + adjust as necessary
To me, these camp socks make the whole socks-with-boots thing feel a little more modern + cool. The socks almost kind of maybe blend with the jeans, making it a subtle look. Can’t go wrong with subtle.
I tried this same combination, but with the socks on the outside of the jeans and … something just seemed a little off about it. It wasn’t for me this time. Maybe later.
I also tried boots with regular, thinner, patterned socks but as cute as the socks were (maroon + white dots!), it just looked off to me. Like it was fun sock day at school … or my jeans were too short … or something.
But that’s just me. And we’re all figuring this out together anyway, right?
And no matter what, we’ll all just laugh at our clothes in a few years anyway, right?
So there’s really no wrong way to do it — wear what makes you feel happy.
Boots: Sam Edelman
Joanna O says
Yes ma’am! Living in central Wisconsin means our winter season starts in November. I often find myself staring at my shoe stash wondering what I can wear that will keep my feet warm. I could use more posts like this one…hahaha!
Thanks for showing how to wear these! I’m always wondering how to wear them and if I look like a total dork doing so. I’ll have to give this a try! :)
Love the comment about laughing at our clothes in a few years! It keeps a fun perspective on getting dressed each day!
COMPLETELY agree with you…we will think we are idiots in about 3-5yrs so LIVE IT UP lol :) and thanks for the tutorial!! I was wondering if we had to have cold ankles to be cool (no pun intended) all winter! So this was exciting to see. Plus, I agree with you, the thick sock definitely makes the difference in being modern. I pictured the socks you described that were thin and KNEW I would feel like everyone was staring if I did that. GOOD call Caroline! :) Gonna rock this look in GA!
This is a great look and solves my cold ankles problem I have sometimes in the winter with booties!
Lynn @ The Actor's Diet says
This reminds me of grade school attempts to show my socks/hi-top Reeboks!
Oh my goodness YES! And those thick “scrunchy” socks that were made just for that purpose.
Andrea H says
I love it! I have been on the lookout for some “scrunchie” socks. I was considering the over-the-jeans approach, but I really like the “stacked” look you are going for here. Can’t wait to give it a try! Thanks for sharing your trial and error tips with us!
I’m a wimp and live in wool socks all winter! Did I mention I live in TN? Hah. So glad to know I’m not alone! Love this vote of confidence to rock the ankle boots and socks! I played around with my wooly, thick ones the other day and they looked cute with the wooly insides flipped inside out kinda like the leg warmers for tall boots. So glad the ankle boots can live on all winter!
Amanda Bee says
I struggle with the booties/jeans/socks thing so much! It’s the one reason I haven’t really sprung for a pair of booties yet, even though I like the look. I’m going to test this out next time I’m shopping, I love the idea of a pair of black booties for winter.
Amanda Bee says
Adding: I appreciate your realistic style and open way of writing about it. It drives me a little crazy when style bloggers post really impractical outfits for winter. There are some super cold days when bare ankles just.don’t.work. Thanks for keepin’ it real.
Yes! I totally agree! It’s great to wear things that don’t really keep you warm when you don’t get real winter, but posts like this acknowledge the freezing reality that winter is for some of us. I’m working on my “ultimate winter wardrobe” ideas right now because what you wear needs to work for where you live. I like this post because it works for Caroline in Texas and also for me in New England. Thanks for trying and keeping the experimental mindset alive. When I first started revamping my wardrobe awhile back, I wanted this classic style that I wouldn’t laugh at in 10 years, but it’s more fun to not worry about that, experiment and have fun with what you wear and give yourself something to laugh at in 10 years. It’s only clothing. Love your posts, Caroline!!!!
Miranda @ Miranda Writes Blog says
I love socks with boots! ‘Full of beans’ and ‘Feeling one’s oats’ are my two new favorite phrases… Can we make ‘full of beans’ a hashtag? Also a cold weather pansies club?
#fullofbeans — Totally happening! :) :) xo Caroline
Full of beans is a totally normal phrase in the UK :-)
Yes we say it all the time in the UK and I find it hilarious that you find it so funny!
Only you could make me desire to own a $16 pair of socks. But seriously, what a seemingly “simple” post and yet this concept is truly challenging so THANK YOU for sharing your wealth of knowledge! I actually prefer to wear socks with my booties and get made fun of. Now I know how to “work it” better. You’re the best Unfancy Caroline!
Hi Viv! I know — not cheap! :) I just have two pairs though and rotate them out. Works! xo Caroline
Have you checked at Target? I noticed they had some of those merino wool hiker socks, so I wouldn’t be surprised if they had some of this genre. Worth a look, anyway!
Tania [girlwithanakita] says
This is fantastic. I have a friend that just moved to Boston from Houston that is wondering how to wear other shoes besides knee boots in the winter. I am still debating this look. I love seeing this on other women :)
I, too, get full of beans during the fall.
Oh my gosh THANK YOU FOR THIS. I had just been fiddling with socks/ankle booties/skinny jeans, and couldn’t come up with the right combo without it looking totally wonky. I will try this tonight!
I love your comment about ‘we’ll all be laughing at our clothes in a few years’. I always think about that. Especially this short boot, ankle jeans trend. I think it looks great, but it will look so weird in like 10 years. I have a couple of short boots and I just haven’t worn them yet because I’m scared! Hopefully this sock idea will push me over the edge.
I’m dying to try this with my go-to booties, but I’m afraid that since they’re a little lower cut (my ankles are visible) it might look a bit off. But… this inspires me to try it out and see ehat DOES work (maybe a sliver of thin “fun sock day” socks showing at the ankle with cuffed jeans?).
Ok, I am now sold, booties are a must for my winter wardrobe! I am lacking in length when it comes to my legs but this is too cute… here is hoping my little legs can pull it off. Regardless, THOSE botties make me frisky!
oh and cold weather pansies club becomes a real thing I am in. I get happy when it gets below 65 and I can bundle up!
you crack me up! 55 in NJ means i’m still in loafers and mocs, no socks! my last sock-less hurrah! lol
I’m in NJ too! And I agree, it’s still flats weather until it hits 49. And even then I’ll probably do no socks until it snows. :)
Steph M says
Ha, my winter capsule starts in just a few short weeks! My tall boots are in there and I have to say I’ve been wanting to get them out with my cold ankles. :) Socks wouldn’t work with my flat, European-slim red suede booties that I’m trying to wear the crap out of before the snow gets here, but probably with my two pairs that are similar to yours. I’ve honestly been wearing plain dark grey thin-socks with the heeled booties and I think it looks good. But I’ve got some Chelsea booties in my winter capsule and I’m going to want some chunky socks! I used to wear sock-monkey socks back in grade 8/9; this is going to feel a little strange!
Not fashion related but full of beans is a british thing, my parents said it to me all the time when I was a kid!! Also I am so excited to try this look tomorrow!
Love it, Katie! Thanks for sharing! :) xo Caroline
I was actually just trying to figure this out! myself! I never settled on a solution but I’m loving your look!
Full of beans! Hilarious!
Socks are an absolute must in Chicago. Great tips! I have a drawer full of cute, patterned socks and whenever I attempted something like this, it just looked off. I have a pair of camp socks and I need to give this a try!
thanks for taking the time to figure out these fashion details and post about them for us…
you always make so much sense and I love how you just offer an idea and encourage and allow for individual style….
I just love your writing style! And these words ..
“But that’s just me. And we’re all figuring this out together anyway, right?
And no matter what, we’ll all just laugh at our clothes in a few years anyway, right?
So there’s really no wrong way to do it — wear what makes you feel happy.”
I was on holiday in italy twice in the last year and all the girls & women wear ankle boots – they look so fun and stylish. So I bought a pair, of course. But over here in sunny South Africa the trend hasn’t caught on quite as much, well, tbh, not at all really :-(
But I wear my booties with pride and just think, hey! whatever, I am enjoying them, so what if I get a few stares, right? Right!
Right! :) :) xo Caroline
super cute. and i love the “cold weather pansies unite!” hahaha if it ever gets cold in southern california, i’ll be right there with ya. full of beans. ok, this post. totally had me giggling.
The year was 1993. 7th grade me slipped into a pair if HUGE bell bottom jeans as my mother looked on in disbelief. I marched confidently right into my middle school, certain this was going to be the beginning of a new/old trend. I rocked those jokers like there was no tomorrow. However, the trend didn’t seem to catch on ’round these parts. Not sure what the rest of the world was doing as there were no fashion blogs for guidance. Eventually I settled into a decade + of flared and boot cut jeans. I still have one pair of boot cuts stored away, after all, skinnies won’t be around forever! ;)
Question: How does this hold up to sitting down then standing up? When I sit, my (skinny) jeans ride up just a bit, exposing skin when the socks are like this (? or similar to this–I tried it out). Then, when I get up, I have to bend over and re-adjust. Feels kind of fussy. Is it just me?
btw, love the boots. Great design.
I’m not sure I understand… why not just wear ankle socks? =warm feet and no socks showing…
Tania [girlwithanakita] says
It’s just so we can wear ankle boots in the winter. For many of us, there is a gap of air where the pant + ankle boots meet. This way, everything is closed up and toasty for the winter :)
*sigh* I am having issues with my Capsule wardrobe. It is making me realize how much of my wardrobe I am not in love with. Or even in like with. Not enough versatile and quality pieces. And also, taking a trip to West Virginia for the first time in December. Not enough layers to keep me warm for the snow because, yay, Florida girl… Suggestions, please? :)
Hi Caitlin! My very first capsule wardrobe was a bit of a bummer too, because I didn’t shop for a single new piece — I just made myself sit tight and make the best of what I had. As hard as it was, it taught me SO MUCH about my style + contentment + and what to look for when I finally did shop. So, if you’re not in a place where you could/should shop, take comfort that living with these pieces you don’t love is actually going to help you find your style. I realize this may not sound that encouraging. But I hope it helps a little bit. :) xo Caroline
I think this sock, boot, skinny jean looks super cute and great for everyday living. Those boots are super cute, I would not think they are 2.75″ looking at them. I think my skinny jeans must not be skinny enough because I try to do this look and it always looks like I’ve got two stumps.
Shelly at pursuingmommygreatness says
I am jealous of your chilly Austin weather! And YES 55 degrees is COLD. :) That probably doesn’t mean much coming from a California girl who is longing for truly cold weather to start!! (It is almost 80 DEGREES here today.)
I just bought a super cute pair of ankle booties that I’m adding to my capsule and realized that I need to try this thing with the socks. Looks cute and do-able!
Thanks Caroline for experimenting with your minimalist fashion and sharing it with us!
When I first read this post, I kind of brushed it off (side note: I absolutely love your blog and avidly watch for new posts!). But for the last two days, I’ve found myself doing this exact thing! So, just wanted to pop back in and thank you for giving us the helpful ideas that we didn’t even know we needed! :)
What is the color sock you are wearing? JCrew shows a black and a mink ivory-not sure wish one you have on. Love this idea! Thank you!!
Hi Cathy! Mine are black. :) xo Caroline
What color socks should you wear with black ankle boots ? Sorry to ask but this is totaly out of the box for me.
Love the jeans! Which madewell style are they?
I want these boots!!!!
Any idea of what they’re called and if they might still be available?
She provided a link to them in her post, but looks like they are sold out now (probably thanks to this post!)
Sam Edelman – Lucille in Whiskey
Does this still apply if you are over 40 and work in a corporate environment? Or should I just start laughing now?