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Un-Fancy

fall outfits, Outfits: Fall

How to wear ankle booties with jeans / part II: socks!

12/02/16

Tis the season for socks!

In yesterday’s post, we talked about three different pairs of ankle booties — short, medium, and tall. Today we’re talking about how to style them with warm, wooly SOCKS! For each pair of booties, we’ll look at four elements — the booties, the jeans, the socks, and why it works. We’ll even get into my favorite no-show socks. Sound good?

In Texas, it’s usually warm enough that I can wear my booties sans socks all the way through the fall. But, once the temperature dips to 50 degrees, this girl wants her socks. Because warm ankles are where it’s at.

No more cold ankles for the sake of style. We can have the best of both worlds.

Before we jump in, I want to let you know that you’re going to see the same socks over and over again. When creating the looks for this post, I felt like I should branch out or present more options. So I tried several other types of socks  — patterned socks, thinner socks, colorful socks — but to me, nothing could beat the look of a thick camp sock.

So I decided to stick with what I love, and focus on showing you what I’m actually wearing, day in and day out — even though it’s all got a similar vibe. Sometimes, it’s nice to just stick with what works.

ONE: SHORT

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The booties: Minimalist ankle booties by Fortress of Inca (similar for less here). Three and a half inch shaft height. Three inch heel.

The jeans: Flares by Paige Denim (old — similar here and here for less)

The socks: J.Crew camp socks (even warmer option here)

Why it works:

I played around with different socks and different jeans, but to be honest, I just couldn’t find a combination that I loved.

Like I mentioned yesterday, when it comes to booties with the front dip, I prefer a good bit of ankle showing. That bit of skin really highlights that dip and flatters the ankle. To me, the socks throw off the look.

So, instead, I shook things up a bit and went with flares instead of skinnies. I can hide the socks underneath, giving me a look I love without sacrificing warmth. Perfect.

If I did want to wear these booties with socks and skinnies, I’d probably opt for my full length black skinnies, a deep cuff that leaves just the tiniest bit of ankle exposed, and a warm no-show sock.

On that note, I have two favorite no-show socks:

This no-show sock from Smartwool. They are pricey, but worth it. First, I have a black pair that I wear with these black booties, and they are totally no-show. Second, they have a bit more coverage and they don’t slip off my heel. YAY.

And this ankle sock from Nike. They have a band around the arch that keeps them in place — no slipping. They would show with a short ankle bootie like my black ones up there, but they don’t show with my medium and tall booties, like the two below.

TWO: MEDIUM

unf-5602-copy

The booties: Boho ankle bootie by Sam Edelman (old — similar here). Four and a half inch shaft height. Two and a half inch heel.

The jeans: Ankle length skinny jeans by Madewell (old — similar here)

The socks: J.Crew camp socks (even warmer option here)

Why it works:

I tend to wear wooly socks with ankle jeans — as opposed to full length jeans, like my black skinnies. The shorter length allows my socks to easily show, which I like. Plus, there’s just less fabric to deal with around the ankle, hence less rolling, less bulk, and less time spent styling.

Here’s how I usually wear ankle jeans with booties:

  1. Turn the hem of the jeans up.
  2. Slip on socks, bunch them up, and tuck them under the jeans.
  3. Slip on ankle booties, and adjust as necessary.

You probably recognize this look, because this is my OG sock and bootie combo. I’ve been wearing this exact pair of booties with this exact pair of socks since 2014. And it hasn’t let me down yet.

Don’t you love when you find a combo that just works?

Want to see all the ways I’ve styled these booties? Right this way.

THREE: TALL

unf-5610-copy

The booties: Rugged ankle booties by Timberland. (Fit note: Runs small and narrow. I sized up half a size and got the wide width.) Six inch shaft height. Three inch heel.

The jeans: Ankle length skinny jeans by Madewell (old — similar here)

The socks: J.Crew camp socks (even warmer option here)

Why it works:

This look is essentially the same as the last one, with one small, but important difference:

It’s subtle.

There’s just a sliver of sock showing with the ankle jeans.

It doesn’t scream I’m wearing socks! In fact, the socks kind of blend in with the jeans, since they have that navy fleck. The socks are an interesting little detail you can find, but only if you look closely.

Since I’m all about subtlety, this look is my favorite out of all of them.

• • •

Here’s a quick-reference guide to everything we’ve been looking at over these past two posts. If you want, you can pin it or save it in case you need some ankle bootie inspiration throughout the fall and winter.

how-to-wear-ankle-booties-with-jeans

Now it’s your turn! Tell me, do you show your socks with your ankle booties? I know I lean heavily towards the camp sock, but what’s your favorite sock to show? And I’d love to hear if you’ve mastered a different way to style a short bootie with socks, like #1. I’m totally open to learning, so share away.

See you Monday — we’ll be talking about one of my go-to holiday outfit formulas. (Hint: It’s super casual.) Have a great weekend, you guys!

xo,

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48 Comments

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Comments

  1. Tanya E says

    December 2, 2016 at 11:59 am

    Tis the season for warm, woolly socks! I agree that the low boots with a front dip don’t look so great with thick socks. I have some low, flat skater-style boots that I can wear with chunky socks and boyfriend jeans but the proportions are different.

    I really didn’t know people wore boots without socks, but looking at your temperatures I can see why! We have had proper winter coat weather this week, but it might get milder. More challenges for the capsule wardrobe.

    Reply
  2. Madeleine Rose says

    December 2, 2016 at 11:59 am

    Heck yes! This is ridiculously helpful. I’ve been on “how to style socks w/ ankle boots + jeans” struggle bus for awhile and this really helps!
    Also, for anyone on a budget who loves ankle boots, I recently got a nice (surprisingly) quality pair of Chelsea Boots from H&M a month or so age. Nice distressed caramel brown leather and shearling lined, so they are so comfortable and cozy. Under $40 too!

    Reply
    • Caroline says

      December 2, 2016 at 10:17 pm

      Madeleine, those sound so comfy! Are they these ones? Thanks for sharing :)

      Reply
      • Anonymous says

        December 3, 2016 at 7:07 pm

        Maybe these ones? I just bought these today. http://www.hm.com/us/product/17999?article=17999-D

        Reply
        • Madeleine Rose says

          December 5, 2016 at 7:54 am

          Yep! The link Anonymous sent are the ones. LOVE EM. It’s funny- when you find a pair of shoes you really like, you find so many creative ways to incorporate them into your closet!

          Reply
      • Madeleine Rose says

        December 5, 2016 at 7:55 am

        The ones Anon linked below are the ones, actually!

        Reply
  3. Nancy says

    December 2, 2016 at 12:10 pm

    Hi Caroline, this was so helpful! The weather in Seattle has been dipping lately and I’ve been desperately trying to keep warm. I usually wear ankle boots with an slightly slimmed down shaft, so I wear thinner socks in a contrasting neutral color. Same concept, but altered slightly to fit the shoes I currently have. :) Have a wonderful weekend!

    http://www.smallerslower.com

    Reply
    • Phoebe says

      December 2, 2016 at 7:00 pm

      So, what’s a contrasting neutral combo? Gray + brown?
      -thanks!

      Reply
  4. Anna W says

    December 2, 2016 at 12:28 pm

    I NEEDED THIS! I am constantly cold and I typically reserve booties for my wide leg wool work trousers, as you did in the low bootie example, but I always reach for my tall boots with skinny jeans. I’ve always felt I was missing out on some interesting styling combinations, but I just can’t do cold ankles! Thank you, thank you, thank you!

    Reply
  5. Anna W says

    December 2, 2016 at 12:39 pm

    Another comment – I can’t stand having zippers on my shoes, but I typically find that booties with a stretch component also tend to have “comfort” styling. I’m all for comfort, but I’m not so interested in a giant black sole weighing down the beautiful simplicity of a nice leather shoe.

    I love the inclusion of the Timberland boots on this list, but anyone out there have some great suggestions for a quality, comfortable, stylish low or mid-height bootie with no zipper? Thanks!

    Reply
    • Caroline says

      December 2, 2016 at 10:28 pm

      Hey Anna, have you tried Everlane? They have a great selection of beautiful leather shoes with no zips! :)

      Heeled: http://bit.ly/2gQxBNn
      Flat: http://bit.ly/2gx9we6
      Ankle: http://bit.ly/2h4bAel

      Reply
      • Anna W says

        December 3, 2016 at 6:56 am

        Ooh, thanks for the tip!

        Reply
    • Oksana says

      December 4, 2016 at 3:20 pm

      If you are willing to make an investment, I can’t say enough about Frye’ chelsea ones, they have several heights. Mine didn’t need any breaking-in, I wore them for hour since day 1
      http://search.thefryecompany.com/search?w=Chelsea

      Reply
      • Anna W says

        December 5, 2016 at 7:55 am

        Awesome, thanks!

        Reply
        • Anna W says

          December 12, 2016 at 10:37 am

          I ended up finding some that fit my style bill – they still have the zipper, but it’s fairly understated and I don’t hear it or feel it when I walk: http://shop.nordstrom.com/s/sarto-by-franco-sarto-garfield-western-bootie-women/4327886?origin=category-personalizedsort&fashioncolor=MUSHROOM%20LEATHER

          Reply
  6. mel says

    December 2, 2016 at 12:56 pm

    i would like to see this with the full outfit shot to get the whole effect. ;)
    ox

    Reply
    • Carol says

      December 2, 2016 at 3:08 pm

      I would too.

      Reply
      • Caroline says

        December 2, 2016 at 10:29 pm

        More photos coming soon, ladies! :)

        Reply
  7. Alyssa says

    December 2, 2016 at 1:00 pm

    I’m all about the tall shaft boot styles — but my own tall shaft boots are one of my F/W outfit staples. I usually wear them with skinnies and a sweater or tunic, and sometimes with socks showing, sometimes without. It gives a nice long and lean look, but with plenty of space to bundle and layer up top. But three cheers for J. Crew socks, I always love the pairs I get there!

    Reply
  8. Lisa says

    December 2, 2016 at 1:05 pm

    Love this! One question though – do you feel like your booties ever get stretched out by wearing thicker socks? I hardly ever wear socks with my booties for fear of this. Do you buy the same shoes in two different sizes? One for socks, one for not?

    Reply
    • Caroline says

      December 2, 2016 at 10:31 pm

      Hey Lisa, I don’t usually buy shoes in two different sizes — and even with socks, I haven’t experienced the shoes stretching so much that they’re unwearable. Maybe my socks aren’t super thick! But they’re warm enough for Texas winter. ;)

      Reply
  9. holly says

    December 2, 2016 at 1:14 pm

    Hi Caroline-
    I just wanted to mention again that socks are easy to find made in the US! You can find local socks anywhere you look. I try to avoid unethical brands that pay no mind to labor standards. I’ve found camp socks…wool….dress and athletic ones that support jobs right here in Marshall’s, TJ Maxx, and Walmart! They also make great stocking stuffers!

    Reply
    • elie says

      December 2, 2016 at 2:55 pm

      TJ Maxx is where I always get my socks! They’re so much cheaper and it’s still the same awesome quality! I’ve given those socks to my friends who camp and travel a lot. Still thank me after every trip they go on for those socks!

      Reply
    • Caroline says

      December 2, 2016 at 10:31 pm

      Thank you for sharing Holly! :)

      Reply
  10. Jenn says

    December 2, 2016 at 1:35 pm

    I am encouraged to try it with my closet. Cannot say I’m entirely sold yet on the look, but I will at least take it for a spin in my bedroom mirror for functionality’s sake.

    Reply
    • Caroline says

      December 2, 2016 at 10:32 pm

      Great Jenn! Hope you try a few different looks and find one that you like ;)

      Reply
  11. elie says

    December 2, 2016 at 2:53 pm

    California has been a bit chillier than usual and this is actually helpful. My booties and sock game isn’t on point any more! California is always warm and tolerable weather, so it’s basically a sock-free zone. Thank you for this post!

    Reply
  12. Robin says

    December 2, 2016 at 2:58 pm

    Thanks for the no show sock tip! I just ordered the Nikes and am hoping for no more bunchy sock boot issues.

    Reply
    • Caroline says

      December 2, 2016 at 10:33 pm

      Woohoo! Hope they work out for you, Robin. :)

      Reply
  13. Sara says

    December 2, 2016 at 4:21 pm

    Hi,
    I have a very off topic question. What kind of all purpose sports jacket would you recommend for a guy? Something to wear to the ballet but then also to a jazz club. Something hip, not middle aged man. i love your style so I know you’ll recommend something I like!
    Thanks!

    Reply
    • Caroline says

      December 2, 2016 at 10:49 pm

      Hey Sara, I’d recommend something in a neutral (gray, brown, or black) and I think the fit would be most important thing about it, since it should look sleek and modern without being fussy. So make sure your guy tries it on and possibly gets it altered to get a great fit. This one is nice because it has a little texture to it: http://bit.ly/2gXcAwI

      Reply
      • Sara says

        December 5, 2016 at 4:08 pm

        Thanks so much!

        Reply
  14. Jill Sarkozi says

    December 2, 2016 at 4:49 pm

    These were awesome posts! Love this kind of stuff –keep it coming! And btw, I needed some socks, so thanks for doing that research for me! :)

    Reply
    • Caroline says

      December 2, 2016 at 10:34 pm

      No problem, Jill. ;)

      Reply
  15. Thays Dos Santos says

    December 2, 2016 at 7:08 pm

    Love all the different ways you styled each bootie. I have only used booties without showing my socks but I actually really like the way it looks with socks showing.
    Thays,

    http://www.simplythays.com

    Reply
  16. Charmaine Ng says

    December 3, 2016 at 6:51 am

    Omg, this is SUPER helpful. I’ve always had trouble with socks and boots. This clears everything up.

    – Charmaine
    http://charmainenyw.com

    Reply
  17. Sydney says

    December 3, 2016 at 7:56 am

    I know leggings aren’t quite your style, but I LOVE wearing my low ankle booties with camp socks over leggings. I put the leggings on, then pull the socks all the way up, put my booties on, then bunch the socks accordingly. I find the socks add a nice chunky element that contrasts with the body-hugging silhouette of the leggings.

    Reply
  18. Marine says

    December 3, 2016 at 10:41 am

    I prefer to wear no-show socks with my booties, because I love the little bit of skin peeking out too. But, if it’s simply too cold out to do that, I’ll wear cute patterned socks, so that the little bit that peeks out is fun. My favorite are white socks with tiny black polka dots :)

    Reply
  19. Whitney says

    December 3, 2016 at 11:25 am

    Just have to share a brilliant tip that stopped me from buying more boots this winter when things got cold and I started stalking shearling boots online. Shearling insoles. I got some for $15 from uggs, put them in my existing fall boots and now I’m happy as a bug in a rug on coldest days. I even think I could go with no show socks and still be happy and warm. A big win.

    Reply
  20. Mathilde says

    December 3, 2016 at 12:11 pm

    Awesome idea !! I’ll do the same tomorrow ha !

    Reply
  21. STEPHANIE says

    December 3, 2016 at 9:18 pm

    Love these posts about booties, especially since I live in them (I’ll even wear them in the summer!)
    I would love to see a similar post from you about sneakers! I want to get a high top pair of Vans, and I know you’ve had/have some… would love to see what you do with them & jeans!

    Reply
    • Tracy says

      December 15, 2016 at 2:32 pm

      ^Ditto! I love the current sneaker trends but have not purchased any because I don’t quite know where to start.

      Reply
  22. DNU says

    December 4, 2016 at 8:15 am

    Nice post..I ll definitely try this..

    Reply
  23. Megan says

    December 7, 2016 at 11:04 pm

    Great post and great timing as I just received the fortress of inca boots for an early Christmas gift! Does anyone have tips for keeping their leather boots looking nice? Do you use a leather conditioner?

    Reply
  24. Anna W says

    December 13, 2016 at 11:14 am

    Another tip for those of us with chronically cold ankles – I almost always wear sheer nude knee highs in the cooler months when it’s not quite cold enough to break out the really woolly socks or when I want the look of not wearing socks (i.e. getting the most use out of my beloved ballet flats). It might seem like an “old lady” move, but most people don’t notice, and it’s amazing how much that thin layer does to keep my ankles and toes comfy.

    Reply
  25. Emma says

    January 10, 2017 at 3:32 am

    Great post! I always have troubles with socks in my booties. I really like to buy the socks you wear here, however I’m from the Netherlands and the shipping cost are radically high! Do you have an alternative from other socks which I can buy in Europe?
    Thanks!

    Reply
  26. Katie says

    November 24, 2017 at 4:41 pm

    I know this is an old post now, but thanks so much for addressing the SOCK ISSUE! I live in New England, and I get cold anyway as it is, and I’m so sick of people posting “fall” or “winter” or “cozy” outfits with half their foot or ankle hanging out! Like, hello? haha. Thanks for the post. I’ll be using these techniques to style my WINTER boot looks. :)

    Reply
  27. Jessica says

    February 2, 2019 at 2:54 pm

    If anyone is reading this post in Feb 2019 and is looking for a pair of Fortress of Inca’s Adriana Coco Booties (short black ones shown above), I’m currently selling mine (like new just a tad too small for me) on Poshmark. Thank you!

    Reply

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