how to style knee high riding boots for 2017 modern

Are Knee High Boots Still in Style?

Fashion Advice

Hi Allie, I have three pairs of knee high boots. They’re really nice quality and I paid a lot for alterations. I don’t see a lot of knee high boots on bloggers these days. Are knee high boots still in style?

how to style knee high riding boots for 2017 modernIf you don’t already own a pair of riding or knee-high boots, don’t buy any this season. While such boots are pretty classic, the problem is the trend so over-saturated the market it was inevitable for it to fade from view. The trend has gone shorter – ankle boots or booties are more versatile, chic, and also usually lower priced. If you already own some basic ankle booties, consider trying an embellished ankle boot which is very hot this fall and a fun way to update a closet of basics.

When a trend becomes a meme you know it’s ready for it to go out of style…

But what about all of us who own and love quality knee-high and riding boots? Is there any way to wear them and look stylish and modern? Below I provide a few suggestions on how to wear knee-high boots in a manner that is current and not at all Han Solo.

how to style riding bootsShop the Look:
sweater | black jeans | riding boots | sunglasses | bag

This look incorporates a classic pair of black riding boots. Keeping the look slim and tailored, the bulk of the knee-high boot is balanced and modern. With the pant (this is a skinny jean, but could easily be switched out for a skinny black pant in ponte or another heavyweight stretch fabric) in the same color as the boot, there’s less contrast, creating a more modern effect. I specifically chose a neutral sweater in a color not too much of a contrast from the black to keep elongating the line. Choose modern accessories that aren’t too equestrian or too rocker chic to make the boot look contemporary.

how to style knee high bootsShop the Look:
dress | bag | necklace | heeled boots

Another way to wear knee-high boots in a current manner is by embracing the boho trend. A long flowing floral skirt can work quite well with riding boots, or a heeled style as featured in the graphic. Depending on your dress color, you can make it work with brown, black, and even other colors of boots. Choosing a dress with a lot of flow (rayon, chiffon overlay, fuller skirt or layers) will balance the bulk of the boot. If the boot is bulky or thicker at the ankles, go with a longer dress. If the boot it more sleek, it could work with high-low or midi length dresses.

how to style riding boots 2017Shop the Look:
sweater | skirt | scarf | bag | boots

Think classic when trying to style a pair of knee-high boots this season. Wool a-line and midi skirts, plaid or crested blazers with jeans, slim sweaters in merino, cashmere, a cableknit. A bit of collegiate style, a bit of Ali McGraw. Stick with autumnal colors and neutrals so it looks luxe and the boots blend in. add classic accessories – a gold watch or link bracelet, silk scarves, satchels or traditionally shaped smaller bags.

What Not to Wear with Knee-High Boots

There’s a few looks you should shy away from when wearing riding boots or knee-high boots in 2017. Unless it’s your signature style, these combinations can look dated this season:

  • Knee high boots with puffer vests – this is true Han Solo style, and the reason the riding boots fell out of favor in the first place.
  • Knee high boots with ponchos or ruanas – Again, veering into Star Wars fashion territory. The goal is to make the boots looks sleek, not utilitarian
  • Knee high boots with cropped pants – For a while, some were styling knee-high boots under wider gaucho-style pants. This is a look that looks good on very few, those that can rock it are likely not reading this blog. It may seem like a smart way to extend the season for cropped pants, but the look really distorts your body and just makes it look as though your pants shrunk and you’re hoping no one noticed.
  • Knee high boots with lots of layersUtility jackets and vests, tunics with multiple layers, tunics with long scarves… all this bulk from head to toe looks dated and isn’t doing any figure any favors.

What to Wear with Knee-High Boots

Beyond the looks featured above, here’s some tips to make your knee-high boots look modern and fresh this season:

  • Elongate the line. Pair black boots with slim black pants to balance the bulk of the boot. Balance the boot with fitted and tailored tops and jackets. Don’t pair the boots with a skirt that is shorter as it segments the body.
  • Don’t let the boots steal the spotlight. Style the boots with longer skirts, with pants of the same color, in ways where they complement the rest of the look but aren’t the focal point.
  • Accept them for what they are. When you try to make your riding boots look rocker chic, it looks dated. These are classic boots with classic equestrian style and should be treated that way. Style in classic, equestrian, or boho ways that embrace the style of the boot.
  • Baby your boots. Unless it fits your personal style, a pair of beat up knee-high boots is going to look like… well like an old pair of boots you’re trying to still make relevant. Polish them up, get them reheeled and resoled. If they’re past their prime maybe it’s time to retire them.


  • Jennifer Buller Velasquez October 21, 2017

    In the same boat, but i guess i’ll pass on boots that cost as much as my january utility bill and get a second pair of booties.I always had heavier calves and thighs.

  • Lorena Lorena October 18, 2017

    I admire them on others but I just gave mine away – i had held on to them for years but then realised that living in a country without winter or fall it just made no sense !

  • Ros October 5, 2017

    I’m on board with the people saying “these boots are comfortable and will be pried from my cold dead hands” 🙂

    Separate question, and totally not the aim of this post, but: I LOVE that long dress. Love. I live in long dresses all summer, and kinda love the look through fall, but can’t style it for fall/winter (shoes? Boots? Especially since I’m chasing 2 small children when not actively at work, heels aren’t ideal, so…? How DOES one style this look in a non-dowdy way?)

  • Mrs.M in MI October 4, 2017

    Yeah, you’re going to have to pry my riding boots from my cold, dead feet. Here in Michigan, I wear them all winter long with minis, fleece leggings, and thick wool socks inside because it’s the warmest. Can’t do that with ankle boots.

    My current vendetta against ankle boots is that I need to replace my basic slim leg jeans after five years and I cannot find a pair of jeans that covers my ankles!

  • Allie at Wardrobe Oxygen October 3, 2017

    LOL, I’ll still be wearing mine, but as outerwear, not as part of my outfit.

  • Allie at Wardrobe Oxygen October 3, 2017

    If you love it, rock it! Like others said, the boots are a classic, they just need to be styled differently from the past few years. Just don’t rock them with a puffer vest 🙂

  • Jill October 2, 2017

    I think riding boots are timeless. I personally think it is the brown boot with black pants that went out of fashion. The thigh-high, embellished and sock boots (!) will come and go, but a riding boot is classic.

    • Allie at Wardrobe Oxygen October 3, 2017

      I agree it’s a classic and not something one should toss from their closets. I think however to keep them looking classic and not like five years ago they need to be styled differently.

  • Michelle Van Ellis October 2, 2017

    I’ll keep wearing them. I have my DUOs thanks to you and a couple of cheap pairs too. I had purchased a extra curvy calf from DSW last month that I had to return, they were too big! I couldn’t believe it. I love the stylings you have here. Pinning!

    • Allie at Wardrobe Oxygen October 2, 2017

      Awesome! I’ll be wearing my DUOs this winter too. And did you see DUO is back? They haven’t been receptive to chatting with me, I’d love to know what the difference is between now and then!

      • Michelle Van Ellis October 2, 2017

        Hmm, looks like the difference is the names reverted but they’ve kept the Ted & Muffy pricing. Boo! Hiss! They are a terrific product so I’ll wait for clearance sales.

        As for booties, well, I’m a shoe whore and already have about 10 pair. :-[ ]

  • Krista Alexander October 2, 2017

    Thanks for this! I LOVE my over the knee suede boots. They’re flats, really comfy and totally me. Even in Florida we wear boots in the “winter”. And when I travel north they keep me warm without having to pack 12 layers of clothes. I will be rocking mine this winter with that rainbow skirt I ordered from etsy (you know the one) my tight fitting t-shirt and my leather jacket.

  • Danielle Keister October 2, 2017

    I love knee-high (and thigh-high) boots. I never pay attention to trends anyway. For me, they are classics that can adjust to any style and era.

  • Christine October 2, 2017

    Thank you for this great post. I’ve got 3 pairs of these boots that I adore. Now I can wear them confidently. The hard part may be finding skirts in the right color. I may have to dust off the old sewing machine that hasn’t seen action in 20 years. Now a request! Can you do a post on what seems like the new “prairie dress” trend? I’m short and I’m not sure these dresses will work on me. But I love the look of them, especially with boots.

  • Anya October 2, 2017

    For fhe first time in many years i must disagree. Knee and overtheknee styles are all over the runway and reta too ( need no further looking than zara for example or hm or any mainstream retailer) after a couple of seasons of booties reigning. I would say they are much more sleek and autumnal with mod vibes or 70s boho looks than the last iteration. Alternativeyl the thigh high is either flat or with a low block heel square toe or pointy toe smallish stiletto. i see it in the lastest elle/ whatever i bought. While i wouldn t buy the 80s read /patent style they push. I predict the suede ones will be very popular . Asos is offering a lot of variation on the style also and they re pretty on trend too. Anyway as always we wear what we want.

    • Allie at Wardrobe Oxygen October 2, 2017

      You and I actually agree! The reader wanted to know how to wear the knee-high and riding boots she already owned. There are many amazing tall boot trends going strong right now and I love them. This post is focusing on how to work with the boots you’ve had in your wardrobe for a while. Thank you!

      • Anya October 3, 2017

        Yeah 🙂 that s true i guess. I read the response but less so the question it seems

      • Anya October 3, 2017

        Thank you for aswering. I didn t focus on the question being asked. 🙂 the visuals are lovely and yes i ve been tired of wearing my boots with jeans especially more contrasty

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