What to wear with midcalf boots

When I was young, I had a babysitter named Carrie who was very cool in a Joan Jett–meets–Stevie Nicks kind of way. Her style was boho mixed with punk—lots of silver and black and denim—and I was pretty much obsessed with her. She almost always wore black suede boots, and in all my years of shopping, I've never found a pair that reminded me so distinctly of her until I tried on the Giorgia boot by Calla. They came in the mail last week and I literally wore them for three days straight. I channeled Carrie all weekend long, but this was the look I think she'd approve of the most.

Calla is a brand that's dear to my heart, because they make shoes especially for people with bunions, and as I learned last week at the doctor, I now have two bunions on my right foot. I've worn their shoes before (most recently leopard pumps), and what I most love about them, other than the fact that they fit me better than any other shoes in my closet, is how much they don't look like comfort shoes. And while Calla does a good heel, I was immediately drawn to this low-heeled, slouchy midcalf boot—I figured it would be perfect with skinny jeans and leggings (and it is!), but I was really surprised at how great it looks with a skirt too. Carrie would approve. I'm wearing a size 38.5, which is actually a half size smaller than what I normally wear in European shoes—thanks to the bunion-friendly design, you get to wear your actual size in Calla shoes. (If you're confused about what size to order, their customer support is fantastic.) And by the way, if you sign up for their mailing list, you'll get 15% off your first purchase.

I have a feeling Carrie would also approve of my leather skirt—and also that I'm not wearing suede with suede, because that would be too matchy-matchy. (I know I'm carrying a leather bag, but more on that later.) Seriously though, if I'm wearing a leather skirt or pants, I always wear suede shoes. It's one of my weird quirky rules. Anyway, this one is several years old and from Zara, but it has weathered the years exceptionally well, and proves that even a small investment in a classic piece is worth it. And yes, I'm wearing tights—after spending hours retouching the spider veins in my legs, I figured it was for the greater good. (It was also very cold outside.)

I'm so glad it's turtleneck weather again, because I couldn't wait to wear this Free People sweater again (you last saw it transitioning to spring). The fit is a little odd—I sized down to an XS and it's still kind of huge, plus the turtleneck is long enough for a giraffe—but it's like wearing a little cocoon and amazingly, I'm always the right temperature when I'm in it. I actually tend to wear it more with pants in real life; it looks a little less lumpy when it's hanging naturally and not being tucked. Guess I'll just have to feature it again soon!

But back to my bag, I probably should have styled this outfit with a clutch, particularly one that's neither suede nor leather. But to be fair, my beloved Balenciaga bag is made of goat leather, not cow, so it is technically a different material. Also, I've been thinking about this one a lot, because I bought it at Barneys New York at least 15 years ago. I saved up my freelance money for months; I think this bag was $800, which at the time was astronomical to me but now seems almost quaint.  It makes me sad to think about Barneys going out of business, although the store had long lost its sense of whimsy and unique identity. Anyway, I felt very grown-up when I bought this bag, and I still feel very special when I carry it. Plus, I think Carrie would approve.

OUTFIT DETAILS: Free People softly structured tunic | Zara skirt (similar here or vegan version) | Balenciaga bag (current season here) | Calla Giorgia boots


eva @StyleMyThrift said...

love this look!

so comfy!

assuming you are in SF? looks like my native town ; )


Laura B said...

It's so wonderful when you find comfortable shoes that look as fabulous as these! Great boots!

merel said...

What a chic look!
I love the boots :)

x Merel

Nancy 's Fashion Style said...

Would be great if Carrie could see you in this outfit! Love it! I do wear leather boots with leather skirts!

Jessica Jannenga said...

Gorgeous outfit! I love the longer grey cardi and your skirt is beautiful! I have a faux leather pencil skirt, but I wouldnt mind a shorter one myself. The slouchy boots are the perfect pair for this stylish look and they sound very feet friendly! :-)
jess xx

Shelbee on the Edge said...

While I obviously don’t know Carrie, I can definitely see the Joan Jett inspiration in this fabulous look! I love the slouchy boots and the leather mini skirt. The tights are perfect for this season and that bag is so wonderful! What a great investment piece to have for years to come. I love this whole look head to toe! Thanks for sharing and linking up with me this week.


Mica said...

These are such great boots and it's nice they have fond memories associated with them even if they are a new purchase! Your knit looks so cosy too and I liked it tucked into the boots!

I think your bag was a great purchase as well - my balenciaga bags are all ageing beautifully and I'm glad I splurged on them when I did - even if they are a lot cheaper now, haha!

Hope that you had a wonderful weekend :) Thank you so much for joining the #weekdayWearLinkUp :) I just posted this week's linkup, I'd love you to join again!

Away From Blue

Claire Justine said...

Lovely outfit Cheryl. I need a skirt like yours :)

Thanks for sharing at The Weekly Link-Up, I hope you can join us today for The Wednesday Link Up :)