what to wear with OTK boots & an OTK boot outfit

It’s official, I’m obsessed with over-the-knee boots. My walnut suede pair from Cyber Monday (previously discussed here and they are still 40% off, by the way) arrived and they exceed my expectations. It’s a rich shade of dark brown and it’s really lovely with a ton of colors already in my wardrobe. I especially love the walnut suede with blue.

I’m finding that my favorite outfit with the OTK boots is to wear something relaxed with a loose fit to counter the long and sleek silhouette of the boots. A swing dress or tunic top that stops a few inches above the top of the boots make for an easy, stylish and comfortable outfit. You can always wear opaque stockings or your favorite leggings or skinny jeans underneath for warmth or modesty.


Turtleneck swing dress in burgundy, grey, black & olive.

This turtleneck swing dress is on sale for just under $30. I ordered the burgundy, grey and olive. I’d hurry in this dress, limited sizes are available. The online review consensus say this dress runs true to size to somewhat big. I will let you know once they arrive.

Update: I received some of my online order yesterday and this turtleneck dress arrived in sizes XS (in burgundy and olive) and S (in olive). The two colors are really vivid in person, both are great colors to complement the neutrals already in your fall and winter wardrobe. For the price, I was impressed by the thicker t-shirt knit type of material which made the dress drape well and was soft against the skin. Nordstrom’s website description of the material is incorrect (100% acrylic), rather the dress tag says its 58% polyester, 38% rayon and 4% spandex. I was hesitant about the acrylic because it always pills, but no such worries now.

The XS was too short on my body, the length hit at an awkward place on my legs. The fit elsewhere was good, but the overall look of the dress looked like I was wearing a girl’s dress. The Small size was much better, I’m very pleased with the length and the nice slouchy drape of the dress. Unfortunately, the burgundy and black colors are sold out in size Small.

I also wanted to note that I like these swing dresses much more than the Old Navy knit swing dresses. I had ordered several a few months ago and found the Old Navy swing dress to be even more short in length and the sleeves were really tight even though the torso was overwhelming with fabric. Nordstrom’s dress is much more comfortable to wear and the fabric is nicer than Old Navy’s version.


Ruffle hem swing dress in huckleberry.

This boho style dress could easily be mistaken for a Free People number but this is at least half the price. It’s on sale for just under $40. Love this purple shade too.


Cold shoulder swing dress in washed black.

I’ve been wanting to try the cold shoulder look for this fall and winter. I’m so glad I waited for this easy swing dress style that is on sale for $25.

Update: I received some of my online order yesterday and this cold shoulder dress arrived in my usual size of US 4 (fits like 0-2). Similar to the turtleneck dress above, this dress was too short and hit me at an awkward length. Also, the material was thin and the drape wasn’t as flattering as I would have liked. It’s a return for me. I had also ordered a size US 6 in this dress, but it hasn’t arrived yet. I’ll report back if it works or not.

The size US 6 arrived and I still did not like this dress. The material was too thin and the fit was less than flattering on me (too big in the shoulders). It was a total miss, so back it went to Nordstrom.


Floral smocked tunic blouse in navy (more colors/sizes here & here); LAmade leggings in anthracite (old, similar); Stuart Weitzman Lowland over-the-knee boots in walnut suede (more colors/sizes here & here).

This was yesterday’s outfit for a Sunday date night. I was going for warm and comfy with a touch of sexy. The OTK boots are just that in and of themselves. Yet, I raised it a slight notch with my new floral tunic blouse. I love the keyhole neckline and the overall romantic vibe of this tunic. It’s a generous true to size fit, I’m wearing a size XS for reference.

Have you been wearing OTK boots? What’s your favorite look with the boots?

Happy Monday to you! xx


4 Comments (+add yours?)

  1. Tiffany
    Dec 05, 2016 @ 14:28:34

    So Getting the ruffle hem swing dress!!! I love you OTK boots with the flirty free people shirt!!! Perfect! Perhaps I will be getting that too!!! Thanks for keeping us styling!


    • valleyoftheshoes
      Dec 05, 2016 @ 14:57:10

      Yay, I hope you love your new ruffle hem tunic/dress Tiffany! The Free People blouse is at a great sale price at Macy’s right now with an additional 30% off and I highly recommend it!

      Hope you have a great week! xx


  2. vavashagwell
    Dec 05, 2016 @ 19:09:00

    You look great, love the outfit a lot! The boots are totes adorb. I have one pair of OTK Stuarts and pretty much wear them with tights/skirt combo. For some reason I have a difficult time finding nice sweater dresses. This time of year, I gravitate towards wool and cashmere so I can stay warm.


  3. valleyoftheshoes
    Dec 05, 2016 @ 19:33:15

    Thank you very much, vavashagwell! Tights and skirts sound fantastic with the OTK boots. I don’t have that many skirts but I should break out my ruched skirts to wear with my oversized sweaters–thanks for reminding me!

    You can always wear something relatively thin underneath a longline cardigan or cardigan coat. I plan on doing this when it hits below freezing.

    Have a great week!


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