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The Style Files

A lifestyle blog on finding my style--in my closet, home and beyond!

Fashion

A Week of Outfits with Ankle Boots

November 26, 2019

Ever wonder just how to make those ankle booties work in an outfit? Today on the blog, I have several looks I put together featuring a versatile (and practical) shoe: ankle boots. They are great for colder temps as a fall/winter staple. Also, sharing a couple recent jewelry additions to my collection!

I got my booties from Shopbop my booties from Shopbop (which are currently on sale for under $100!), and now is the perfect time to invest in some if you are looking to add them to your wardrobe. Now through Dec 1 at 11:59pm ET with code MORE 19, you can get 15% off orders of $200+, 20% off orders of $500+, 25% off orders of $800+. (Plus, sign up for a free account at Rakuten and get more cash back on top of that. New subscribers get $10 for making your first purchase of $25 or more. That’s free money!)

Styling Tips for Ankle Boots

Throw on a pair of skinny jeans, and my preference is not to have jeans tucked into boots –it looks a bit off to me. So, either give them a cuff so they hit right above the boot or wear ankle length jeans, like I am in these outfits. When the weather is mild, I wear low socks so my ankle still shows – like these. And when it turns cold, you can switch to a pair of socks with a subtle pattern that is in the same tone as your jeans – like these. When it’s a polar vortex outside, there’s no way I’m showing any skin.

Outfit details: Booties (exact) // Denim (similar) // Sweatshirt (exact)

I love a cozy yet casual outfit, and this fits the bill. This quilted pullover sweatshirt is SUPER comfy and the zipper pull and quilting give it some extra detail to dress it up a bit vs. a standard sweatshirt. I usually live in sweatshirts or sweaters these days, and recently added this one to my closet as a birthday gift. The fit is true to size. At under $30 it is a steal compared to the LL Bean version. Fran does a great job comparing the two here. These taupe ankle booties to lighten up the look, too vs black ones.


Outfit details: Booties (exact) // Skirt (similar) // Sweater (Everlane Cashmere V-Neck: shop here)

Whether it’s a holiday party or winter wedding, a pleated velvet midi skirt is a fun option! Normally, I would pair with heels to elongate my legs, but I’m going for warmth/practicality and the booties work. I paired it with the most COZY cashmere sweater from Everlane (such a classic staple) and tied a not in it to define the waist a bit. Super fun!

Outfit details: Booties (exact) // Jeans (Target) // Tank (Target- sold out, similar) // Jacket (exact and on sale!)

I am a fan of leopard print, and this camisole tank is a nice option that is a bit lighter than the standard black based leopard prints out there. I kept a neutral look by pairing with this gray lapel zip jacket and taupe booties for a fun yet coordinated look.


Outfit details: Booties (exact) // Pants (exact, also comes in solid colors) // Sweater (Everlane Cashmere V-Neck: shop here) // Jacket (Old Navy, similar)

Speaking of leopard print, this is a fun dressy/edgy outfit featuring ridiculously cute and comfortable dress pants (that I own in 3 colors). I paired it with my Everlane sweater for warmth, and a moto jacket and black booties. Heels would work great here, but in those cold temps, keeping the skin covered takes priority some days!


Outfit details: Booties (exact) // Denim (similar)  // Sweater (Everlane Cashmere V-Neck: shop here) // Vest (Old Navy, similar)

I love some good layers, and vests are perfect when you need a little warmth without a full jacket. This buffalo plaid is a fun pattern and the vest itself isn’t too bulky. I kept it somewhat neutral with the black sweater and taupe booties, but adding a fun statement earring or swapping the sweater for a more colorful option would be fun too!

Outfit details: Booties (exact) // Denim (similar)  // Chambray shirt (exact)

A basic outfit featuring some versatile staples like a chambray shirt and black denim. This is a somewhat blank canvas, so some fun accessories like earrings or a scarf would be a great finishing touch!

In terms of jewelry these days, I reach for options that are simple, delicate and subtle…especially with an 18 month old! Plus, these items are such a classic choice that never overwhelms an outfit and can be worn every day. I recently added this beautiful watch to my collection. The white and rose gold work so well with the colors that I gravitate towards in my closet. I also added this gorgeous ring with my boys’ first initial on it. A ring is something that I can slip on every day, and I love the rose gold color, as I feel it is the perfect blend between my gold and silver jewelry, like my wedding ring! Check out my current jewelry collection in this post.

Hopefully this post gave you some ideas on how to wear ankle boots. What ways do you like to wear them?

This post is in partnership with Nakturnal and Shopbop. Affiliate links have been used. Each time you click, I earn a small commission or referral. Thanks for supporting the brands that support The Style Files!

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  1. Ryan says

    November 29, 2019 at 3:08 pm

    I like the classic look of these. great post!

    Reply

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Hello


I'm Valerie: full-time mama and wife, part-time corporate gal. Based in the Chicago burbs. Loves coffee, a good workout and chocolate. Aspiring minimalist. I’m in the midst of finding my style– from fashion & fitness to healthy living to motherhood and beyond!

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