Gray Booties | 2 Ways

I’m asking for trouble again, using the word ‘bootie’ in a post title, but it had to be done. And while we’re talking about it, is it gray or grey? I think I use both spellings interchangeably. Shouldn’t I be partial to one? But I’m getting off-topic. Today’s subject is booties…as in, the shoes on my feet. I hope that doesn’t disappoint some of you quirky folks. #andbyquirkyImeankinky 😉

Besides my beloved plum pair, every pair of booties I own is taupe. Which, if you only buy one pair of booties, I recommend taupe…there’s literally not a single color they don’t pair with well. But with Christmas money burning a hole in my pocket, I wanted another color of booties. So I went on the hunt for black, because it’s pretty much the opposite of taupe, and I thought would be a good addition to my wardrobe, as well as give me tons of styling options.

What I discovered was, I really only loved a black boot with black jeans. When worn with other colors, I felt like my feet were so visually heavy, and it chopped my legs. At only 5’4″, I can’t afford to lose any leg! (If you’re looking for black booties, however, I adored this pair that’s currently on sale, and these, that have perfect reviews.) Then I found this pair, and fell head-over-heels #punintended, and realized gray is not only a softer substitute for black, but actually more versatile! Or maybe that was my rationale because I reeeeealllllly wanted the booties.

Peacoat (only $38!) | Striped Sweater | Black Jeans | Gray Booties | Reversible Tote
Sunglasses | Hoop Earrings | Lipstick in ‘Yu’

Obviously black boots would look great with this outfit, but the gray gives it a softer and unexpected touch. The v-cut of these booties helps to elongate the leg, too. And elongating is always a good idea.

Fit Tip: The boots run true to size, and are comfortable enough to wear all day. I love that I can wear a low-ankle sock with them, too.

This peacoat has been in my arsenal for a few years…it’s pretty much the best $38 I’ve ever spent. But size up!

Peacoat (only $38!) | Striped Sweater | Black Jeans | Gray Booties | Reversible Tote

The sunglasses were my big Christmas gift from Mr. SP…and I dare say they’re sexy! I’m such a fan of these $12 mirrored aviators, so if we were going to spend the money for the ‘real deals,’ I wanted something completely different. These all-black frames and lens add a touch of edge to my outfits, and I adore them!

Striped Sweater | Black Jeans | Sunglasses | Hoop Earrings | Lipstick in ‘Yu’

Peacoat (only $38!) | Black Jeans | Gray Booties | Reversible Tote
Sunglasses | Hoop Earrings | Lipstick in ‘Yu’ | Hat

Gray Booties

For a second look, I paired the booties with traditional denim, and as you can see, it’s a softer transition to gray, than it would be to black. Of course you don’t have to always wear a gray or black top with the boots, in fact, gray goes with most every color, but I always jump at the chance to wear this sweater top. It’s honestly as fuzzy-soft as my favorite pajama pants.

Sweater Top | Puffer Vest | Scarf (similar) | Jeans | Booties | Crossbody Bag | Sunglasses

Sweater Top | Puffer Vest | Scarf (similar) | Jeans | Booties | Crossbody Bag | Sunglasses | Watch | Bracelet 

Sweater Top | Puffer Vest | Jeans | Crossbody Bag | Sunglasses | Hoop Earrings

The v-neck isn’t too low for me, but if you’re concerned about wardrobe malfunctions, try layering a lacy bralette over your traditional bra for a peek of pretty.

Sweater Top | Puffer Vest | Sunglasses | Lace Bralette | Hoop Earrings

Not sure what’s happening here, but you know I can’t resist a good outtake.

What color booties do you gravitate towards most? I have to say, in the few weeks I’ve had this gray pair, they’d seen more action than any others in my closet! Happy weekend, lovebugs!

Psssst…the Container Store is back all day filming video of our Master Closet. Follow behind the scenes on my Instagram Story, and cross your fingers I don’t babble. Too much anyway.)

{Shop Outfit One}

{Shop Outfit Two}


{Sales Worth Noting}

Nordstrom // New markdowns up to 40% off, including these popular booties & this cute sweater for Valentine’s Day

Gap // All on sale + extra 25% off with code EXTRA (I just grabbed this crochet top for $23) 

Old Navy // 25% off total order (how cute are these $10 boatneck tees?!)

Loft // 50% off everything with code NOEXCUSES (even the coveted signaturesoft line!)

World Market // Huge furniture sale (including my console table, which is finally re-stocked!)

J.Crew // Extra 40% off sale with code SHOPSALE (this top is seriously tempting me!)

J.Crew Factory // 20% off when you spend $100 with code GOODDEAL (today’s striped sweater included)




Leave a Comment


  1. I agree that taupe booties go with EVERYTHING! I love the grey ones I have from a couple of years ago, but they aren’t super comfy, so I’m always reaching for the taupe. I have a pair of black ones too, and I do pull those out on occasion.

    Posted 1.20.17 Reply
  2. Stephanie wrote:

    I love that striped sweater and I usually hate all things striped.

    I also love blanket sweaters, they’re the best things ever created!

    Thanks for the shopping links!!

    Posted 1.20.17 Reply
  3. Diane wrote:

    I’ve been on the hunt for taupe booties with a flat heel (I can’t wear any heels due to problems with my feet) and you finally convinced me to pull the trigger on that gray sweater. After having sweater envy for weeks, I finally ordered it yesterday!

    Posted 1.20.17 Reply
    • Cassie wrote:

      I have a flat pair of taupe booties that I adore, and honestly get compliments on every time I wear them. You’ve probably seen them 100 times on my blog! 🙂 These:

      Posted 1.20.17 Reply
    • Diane wrote:

      Thanks! I’ll have to check them out to see if they’ll work for me!!

      Posted 1.20.17 Reply
  4. Christina wrote:

    Grey is probably my favorite neutral color. It goes with everything. Those boots are so cute! I love the dip in the front.

    Posted 1.20.17 Reply
    • Cassie wrote:

      That’s my favorite part too. I’ve noticed that boots cut straight across kind of shorten my leg a little. :/

      Posted 1.20.17 Reply
  5. Carla wrote:

    Ok. This is a topic I am very passionate about. It is GRAY. If you look on a crayon, it is spelled g-r-a-y. The English spelling (as in UK) is grey. Here in America we spell it with the a. Why am I so knowledgeable about this? My son is named Gray (not Grayson or Greyson) and it drives me crazy when people refer to him as Grey! #firstworldproblems

    Posted 1.20.17 Reply
    • Cassie wrote:

      LOL…got it!! It will forever be GRAY!! xo

      Posted 1.20.17 Reply
  6. Allison D wrote:

    I love these outfit combos! The second look is definitely my favorite– that blanket scarf is so lovely! Speaking of socks, I just purchased the Lucky Yakeena bootie (like your maroon ones!) in black, but I’m not sure what socks to wear with them. When I wear low-cut ankle socks, they show on the side cut-out. What do you usually wear?

    Also, do you have a recommendation for a good suede protector? These booties are so perfect– I want to keep them in good condition for years to come! Thanks for all the inspiration and tips!

    Posted 1.20.17 Reply
    • Cassie wrote:

      Hi Allison!! Those wedge booties are so dang cute…I do love them in black, too! I have some really low ankle socks from Old Navy (of all places) that work with those boots, but I do have to pull and tuck them a bit to not show. Sometimes I just wear them with no socks so I don’t have to mess with it. As for a suede protector, I’ve never tried anything other than the original Scotch Guard. But we don’t have much weather here, so it’s not something I usually have to consider. xoxo

      Posted 1.20.17 Reply
      • Allison D wrote:

        Thanks so much for the quick, helpful response! You’re the best! 🙂

        Posted 1.21.17 Reply
  7. Jamie wrote:

    Love your black puffer vest!! Do you feel it runs true to size?

    Posted 1.20.17 Reply
    • Cassie wrote:

      They run a little big I think, so I size down. But I also never zip mine, so that’s part of why I prefer it more fitted. xo

      Posted 1.20.17 Reply
  8. You are the cutest!! And I am such a “gray” lover especially shoes! These are so versatile and look so comfy… Yes to all these looks! Have a great weekend 🙂

    Brittany 🙂

    Posted 1.20.17 Reply
  9. Katie wrote:

    For some reason I’ve never been a fan of black boots/shoes but I LOVE gray as an alternative color. I’ve got a pair of cognac booties but may have to check these gray ones out too…

    Posted 1.20.17 Reply
  10. Haley Stevenson wrote:

    Wow! I know you mentioned you interchange things often, but you also seem to buy things in multiples. Your beloved plum booties, also in black, also in gray, in taupe, etc. I am really trying to understand how you justify this to your readers. It just comes across as excessive. Like a commenter said, when is it enough? Cassie, you are darling, have a life that is beyond enviable, and you do let your guard down at times; however, recently and sadly, I am finding you less approachable. I am tired of being directed to rstyle links. Just miss the old “real” Cassie. Humble bragging is still arrogant.

    Posted 1.20.17 Reply
    • Cassie wrote:

      Hmmmm, I only have the plum booties in plum…not sure why you think I have them in every color. It’s never my goal to convey an enviable life, only to create joyful content that inspires women! Thank you for your honest comment, and I’m sorry my site no longer appeals to you. xo

      Posted 1.20.17 Reply
      • Joanna wrote:

        As a fashion blogger, I expect to see new content. If your outfits were on repeat, I would quickly get bored. I certainly don’t buy a lot of what you link to, but can put outfits together that are similar from my closet or shopping locally. Don’t change a thing! We love you for your sweet and honest voice.

        Posted 1.20.17 Reply
      • HS wrote:

        Agree to disagree. I just preferred your old tone. You have your loyal followers (and making bank from them!)Time for me move on. Your passive aggressiveness is toxic, my friend.
        PS-TripAdvisor is for novices! Lol!😳

        Posted 1.20.17 Reply
    • Sarah wrote:

      I have never commented, but also wanted to say please stay how you are…your blog is so refreshing and fun to read! The links are there to help people who want to purchase the item…I have never clicked on them as I’m not in the US…but they certainly don’t bother me. I get inspiration from the way you style things, but never feel pressured. Anyway, you can never please everyone…so just be the best “you” you can be, and never apologize for any parts of your life that are good, we all have good and bad in our lives…but I’d far rather focus more on the good when possible. Rant over, now back to lurking! 😝

      Posted 1.21.17 Reply
  11. Angi wrote:

    I’m a freaky FITness phenom also passionate about all things grey and bootie-licious!
    Your casual put together style is fun and carefree! Your positive spin and charm enhances the shopping experience. As I say in the gym…keep pushing and don’t let one rotten apple spoil the whole bunch!

    Posted 1.24.17 Reply
  12. Adorable!

    I’ve always heard that it’s grAy in America, grEy in England if that helps!

    XO, Jaclyn

    Posted 1.27.17 Reply