5 Boots I’m Loving This Season + How to Style Them

Outfit details: Boots | Blouse | Similar skirt | Bag

1. Every winter I love to stock up on new boots and booties (no one likes cold toes!). I try to keep to neutral colors, so they are more versatile and easy to style. One of my favorite styles are over-the-knee (OTK) boots. You guys have probably seen me style OTK boot’s so many times but it’s really the only time of the wear I get to wear them so I make sure I get as much use as possible 🙂 And I just love how you can wear over the knee boots with jeans, sweater dresses, and skirts…anything really! These BP OTK boots are great for petite calves (I look for boots that have a 13-15″ circumference) and comes in red as well (they unfortunately sold out of the tan color). I also get a lot of questions about how I keep my OTK boots up, and I always wear a pair of knee high socks (like these ones) to help fill them out a little better.

On me: Boots | Sweater dress | Bag
On Jasmine: Boots (tan is sold out) | Sweater dress

2. These super cute almost-wedge booties are a great matte black that are also great at lengthening legs. I wear these with leggings and jeans also. I wouldn’t recommend pairing booties with shorts or skirts right now as it’s too cold!

Boots | Jeans | Jacket (similar one for under $100 here) | Bag

3. Now here’s a cool boot I was so glad to find! It has the perfect shade of everyday brown, perfect for all my casual looks! These go so well with jeans, black or blue. I especially love pointy toe boots as they really lengthen my legs.

Boots | Jeans | Jean jacket | T-shirt | Similar beanie | Belt | Bag

4. A slightly less edgy boot I’ve been loving are boots with a softer toe, lower heel, and lighter shade. These boots go well with cozy, comfy looks, like cardigans and oversized sweaters. I also pair them with leggings or denim for my everyday winter looks.

Boots (sold out, also love these similar ones here and here)| Jeans | Similar cardigan | Bag

5. Last but not least! A classic style of boot I needed for this season where these fab polished leather ankle booties. They have a nice silver ring on each side of the boot, which is why I wish I got a profile shot of them, but alas you’ll have to wait for me to style them again! These go great with anything skinny – whether they be leggings or denim.

Boots (also love these similar ones here and here) | Peacoat | Leggings | Sweater | BagSimilar beanie

Shop the post:


var _gaq = _gaq || []; _gaq.push(['_setAccount', 'UA-33695057-1']); _gaq.push(['_trackPageview']);

(function() { var ga = document.createElement('script'); ga.type = 'text/javascript'; ga.async = true; ga.src = ('https:' == document.location.protocol ? 'https://ssl' : 'http://www') + '.google-analytics.com/ga.js'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(ga, s); })();


  1. Charmaine Ng | Architecture and Lifestyle Blog
    December 21, 2017 / 8:42 am

    I love how you styled each and every one of these boots. Your outfits are the cutest! ❤️❤️Charmaine Ng | Architecture & Lifestyle Bloghttp://charmainenyw.com

  2. Natali Karppinen
    December 21, 2017 / 9:07 am

    All are great pairs and I love the way you've styled them too!https://lartoffashion.com

  3. Simplement Lui
    December 21, 2017 / 9:11 am

    Great outfit with every time the right boots or booties ;)https://4highheelsfans.wordpress.com/2017/12/21/retro-heels/

  4. Rachel Buechner
    December 21, 2017 / 10:29 am

    Excellent blog, Jess!

  5. Izikova
    December 21, 2017 / 5:37 pm

    I love OTK boots too! And I like every way you styled your shoes. :)http://izikova.pl

  6. Ana Vieira
    December 21, 2017 / 5:43 pm

    I love all these looks! <3Blog – Maria Rita

  7. Monika Basiaga
    December 21, 2017 / 6:23 pm

    Beautiful boots and outfits. 🙂 I like them all! You have great sense of style.

  8. Sincerely Ophelia
    December 22, 2017 / 4:00 am

    Boots are everything for Fall and Winter. Love your picks!XOXO //SINCERELY OPHELIA | NYC Petite Fashion Blogger

  9. Elizabeth
    December 22, 2017 / 6:14 am

    Loving all of the over the knee styles so much <3 🙂 XO, Elizabeth http://clothestoyouuu.com/

  10. Kinga K.
    December 22, 2017 / 5:50 pm

    Fantastic outfit,great boots <3

  11. Anonymous
    January 8, 2018 / 3:01 pm

    all 5 styles of boots beautiful ,definitely 5 times over the shoulders-Paul

Shop My Wardrobe