The Gray Ankle Boot Holy Grail

Casual Clothes · Casual Friday · Office Appropriate Outfits - Fall

As I mentioned back when I wore floral and argyle together, I’ve been on the hunt for a great pair of gray booties. I fell in love with the Rag & Bone Harrow style but, alas, they were out of my price range. However! Thanks to my partnership with Shopbop I was able to save my gift certificates for this H by Hudson pair!


Vest – Comfort Me Boutique (similar) | Shirt – Le Tote (same) | Necklace – Jeans and a Cute Top Shop (similar) | Jeans – The Limited (similar) | Booties – c/o Shopbop (same)

So these are now officially the second most expensive pair of shoes I own. And they are worth every penny. But, no worries if you can’t afford them yourself but want a pair of gray booties for yourself! I’ve put together a list of 9 pairs that range in price from under $30 to just under $300 with most being under $150.

Shopping for Gray Ankle Boots and Booties


 Ankle booties are very “in” right now. Second only to riding boots, I would say. Of course, they don’t keep your ankles as warm as riding boots so don’t forget to wear socks with them! And if you’re not sure how to wear your skinny jeans with ankle boots, try rolling them at the ankle like I did in today’s outfit.

gray-hudson-ankle-bootsSpeaking of today’s outfit, I’m not in love with the top half. Every time I wear this vest I feel like Spongebob Square Pants. Except square and black and furry instead of square and yellow and porous.

plaid-shirt-faux-fur-vest-2No, I do not have kids. Yes, I still know words to the theme song.

Anyway! I do love faux fur vests but maybe I should look for a more fitted one? Or just accept the fact that this one, while soft and fuzzy and pocket-having, just doesn’t work for me and own it regardless.

Linking up with Work Clothes, I Suppose for Third Thursday Threads

3 replies on “The Gray Ankle Boot Holy Grail

  1. Melissa

    If you don’t love the vest—I’m a strong advocate of parting with it. (Something I’m always/actively working on with my own closet) Because at the end of the day, if you don’t 100% love it (no matter how much others encourage, etc) you won’t project the confidence that comes with wearing something that you truly love.

    I had this same issue with a blazer the other day. Beautiful blazer at Banana Republic, the associates were very complimentary, but I felt it was too boxy/ too long and ultimately like I was playing dress up with someone else’s blazer. So no matter how nice it looked, I wouldn’t have felt great in it and ultimately I left it behind–no regrets. (Though I’m trying to get my work BFF to buy it because I do think it would look fabulous on her! hahaha)

  2. Gina @ On the Daily Express

    I’m in agreement with Melissa there – if I don’t LOVE something (or at least feel pretty good about it when I’m wearing it), then it needs to go. Lesson learned, no regrets, moving on to something that I actually enjoy wearing. e.g. the way you feel about your booties vs. the way you feel about the vest! And speaking of those booties, glad you got a fantastic pair that works for you, even if they weren’t the Express ones! Sounds like it all worked out.

    And P.S. By nominating Chicago for the Midwest on my next Trend Survey, you are officially nominating yourself to fill out the survey and be my Midwest trend reporter, so thanks for that! 🙂
    Gina – On the Daily Express

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