1. WITH A SHIFT DRESS & HAT
SIMILAR BLACK DRESS HERE AND HERE || SIMILAR BOOTIES || SIMILAR BLACK CLUTCH || SIMILAR BLACK HAT || BROWN LEATHER WATCH || LADDER CUFF
Booties work great with a longer shift dress because they don’t take away from the dress like a taller boot might. And adding a hat gives the look an extra element of style, while still keeping it casual.
2. WITH WHITE DISTRESSED JEANS
SIMILAR GREY TEE || SIMILAR WHITE DISTRESSED JEANS || LEOPARD BOOTIES || SIMILAR BAG || SUNGLASSES || LADDER CUFF || SIMILAR EARRINGS
White distressed jeans are really easy to play up with booties because you can wear pretty much any color or pattern with them without going wrong. These leopard booties have a lot of detail, so adding a simple grey tee is all that is needed.
3. CASUAL & DISTRESSED SIMILAR STRIPE SHIRT || DISTRESSED DENIM JACKET || SIMILAR BLACK DISTRESSED JEANS || TAN BLOCK HEEL BOOTIES || SIMILAR BAG || SUNGLASSES
Mixing dressier booties like these block heel sandals with a casual, distressed look pulls everything together. Mixing nicer pieces with more causal pieces is the key to a successful street style look.
4. TUCKED INTO LEATHER PANTS BLUE OVERSIZED SWEATER (wearing a small) || SIMILAR BLACK FAUX LEATHER PANTS HERE AND HERE || BLACK STUDDED BOOTIES || BLACK BAG || SUNGLASSES
Tucking a taller pair of booties into leather pants elongates your legs, and effortlessly dresses up your look. Adding an oversized sweater keeps the look casual without taking away from the booties.
5. BLACK ON BLACK + A NECK TIESIMILAR WHITE TEE || SIMILAR FAUX LEATHER JACKET || SIMILAR BLACK DISTRESSED JEANS || SIMILAR BLACK BOOTIES || BROWN LEATHER BAG || SIMILAR BANDANA || SUNGLASSES || GOLD CIRCLE BRACELET || TURQUOISE RING
Black booties work with black jeans because they blend the look together without becoming a distraction. And adding a necktie draws your eyes up to balance the look out.
6. WITH A PENCIL SKIRTWHITE TOP (wearing a small, low in stock; similar top here) || BLACK SKIRT (wearing an XS) || WRAP BELT || BLACK BOOTIES || BLACK SHOULDER BAG || GLASSES (only $12! and the perfect size frames) || BLACK RING || GOLD CHOKER || GOLD BALL HINGED BRACELET
Booties with a heel that come up slightly higher than your ankles work best with pencil skirts. Because pencil skirts are fitted, finding a boot that fits snug without too much gapping around your leg is key.
7. WITH A LONG CARDIGAN
SIMILAR GREY TEE || SIMILAR LONG CARDIGAN HERE AND HERE || SIMILAR JEANS || SIMILAR BOOTIES || TORY BURCH BAG || SUNGLASSES || BROWN LEATHER WATCH
With a longer dressier cardigan you can get away with wearing booties with a heel on them. With a simpler cardigan, adding booties with less of a heel would keep the look more casual.
8. ADD A VEST
SIMILAR WHITE SHIRT || SIMILAR LONG VEST || SIMILAR DISTRESSED JEANS || SIMILAR WEDGE BOOTIES || SIMILAR SADDLE BAG || SUNGLASSES || BROWN LEATHER WATCH
Adding a long vest dresses your look up the same way a longer cardigan does. Pairing a vest with wedge booties plays up that layered, feminine look well.
9. MAKE IT PREPPYRED SCALLOPED SWEATER (on sale! I’m wearing a small; comes in 7 colors!) || SIMILAR STRIPED LONG SLEEVED TOP || JEANS || SIMILAR BOOTIES (on sale under $80) || SUNGLASSES || SIMILAR SADDLE BAG
Preppy looks can easily include a chunky heeled bootie to add style and sophistication. Opting for a unique bootie gives the look a bold flair.
9 thoughts on “9 WAYS TO STYLE BOOTIES THIS FALL”
I need to add a new black pair to my closet!
Back was one of the last colors I added, and I wear them a lot more than I thought I would!
Love it!! I wish I could find a nice pair of brown booties, the ones I loved they were sold out…
Bummer Maria! Which ones were they? I’ll keep an eye out for something similar…
#7 & #8 are the looks I’d most likely wear. I take inspiration from your wonderful style and then I accommodate it for my size 16-18 body. Sometimes I am even able to buy things in my plus sizes from your links! And it’s been fun! My amazing, handsome husband and beautiful grown daughters are noticing my efforts and they’re super supportive. Thanks Leanne, for being this fluffy wife/mom/granny’s style guru!
Hi Gina! This makes me SO happy to hear! I am so glad I’ve been able to help you out a little ad how great that your hubby and daughters notice! That has got to feel great! Keep it up!
Here’s a question… Do you wear the booties that show more foot, like #9, with any sort of sock or anything on your foot? I love to wear them, but my feet have been freezing here in Utah!
Hi Ashlee! The deep cut in #9 doesn’t really lend itself to a sock. I normally don’t wear socks with my booties, but I’ve also experienced the crazy Utah winters! I would opt for a ankle boot without the side slit (like #1, 6, and 7) and wear it with a thick pair of wool socks. Then I would style it with skinny black jeans and tuck the jeans into the boot so the socks would stay hidden but you would also have the warmth. Hope that helps!
Thank you for sharing the guide! There are so many way to dress with booties.
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