Ankle Boots Outfit Combos

If the Boot Fits…

US Polo Assn 2-Rudy found on Polyvore. These boots look more like Timberlands though they almost resemble the ones Mollie chewed except these ones are tan in color.
US Polo Assn 2-Rudy

My first excursion into the world of ankle boots began with a fixation on work boots that bordered on a fetish. It made no sense to me that a self-professed professional would be so fascinated with this type of footwear but I know where it all started.

I’m pretty sure I’ve mentioned that my ex-husband, Chuck, was the best contractor I know. He took such care in making sure whatever he did was done to absolute perfection.

When we bought our home some of the work Chuck did involved tearing a hole to the outside wall of the dining room then installing French doors, totally revamping the living room, replaced windows throughout, built a new porch and put up new siding. Since I had a vested interest in our home many times I would work alongside Chuck.

I don’t remember ever telling him how much I enjoyed watching him work. This was the beginning of my work boot fetish because he looked so darn good in them it drove me crazy.

Grey long cardigan, grey boots, black tank, black handbag, blue denim jeans.
Grey & Black Pinterest/Polyvore

It took me months to find the right pair as I initially thought I wanted Timberlands but the ones that spoke to me the loudest were these magnificent pair of black leather Polos. I can’t tell you how much I adored these boots and I was able to keep them up until last year when Mollie decided she wanted to chew them and in the process broke my heart.

A couple of weeks ago I did a post titled Of Shoes and Shrimp where I talked about the different styles and types of boots and I thought why not do follow-up posts on how to wear each style. Hence today’s post on ankle boots.

It seems everywhere I turn I’m seeing ankle boots and cuffed jeans. There seems to be disagreement on cuffing jeans with a little ankle showing versus inserting them into the boots. However I’ve seen them worn both ways although my favorite look is wearing jeans cuffed. One thing worth noting for cuffed jeans with ankle boots you’ll want to wear skinny or straight leg jeans.

Pastel Plaid Scarf, cardigan appears to be a blush color & ankle boots by steffiestaffie found on Polyvore. White tank, black denim, beige ankle boots & handbag
Pastel Plaid Scarf, cardigan & ankle boots by steffiestaffie Polyvore

Other looks I like are the skirt or dress with tights and leggings. When adding a cape or wrap to any of these looks the end result is très chic. Playing with different colors, textures, layers and accessories like scarves, hats, bags, and gloves provides endless options.

Throughout today’s post are pictures I found on Pinterest and Polyvore of ensembles I like. The heels on the grey boots are little high for my tastes (I never thought I’d say that) but they were too sharp to pass by so I’m sharing. The descriptions on the photos will be in Alt Text. Below I provide some combination examples.

  • Burgundy, Grey & Black
    Chunky cowl neck burgundy sweater
    Charcoal grey midi skirt
    Black tights
    Black ankle boots
  • Dark Denim, Black & Grey
    Cuffed dark skinny jeans
    Charcoal grey tank
    Grey/white leopard print cardigan
    Grey/black plaid ankle boots
  • Black and Burgundy
    Black leggings
    Black tunic sweater
    Burgundy scarf
  • Dark Denim, Black & White
    Dark Rinse Cuffed Skinny or Straight Jeans
    White tee
    Black blazer
    Black & white scarf

I hope you enjoyed some of my suggested combinations, I’ll be putting together additional combos for other boot styles in the coming weeks.

Have a wonderful weekend!!

“Dogs laugh, but they laugh with their tails.” ~Max Eastman, Enjoyment of Laughter  Or in Mollie’s case she laughed when she tore up my boots.

Author: Steph McCoy

Hi I'm Steph, a businesswoman, style setter, blogger, and abilities crusader who breaks the myth that “blind people can’t be fashionable.” “It’s about walking boldly with confidence, transcending barriers and changing the way we perceive blindness”

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