When it comes to fall and winter dressing, my approach hasn't changed much. I'm still firm on the idea that anything I invest in should be both comfortable and versatile. City walking is a regular part of my life, so my shoes need to hold up well during those long strolls. At the same time, I want them to transition easily between casual and dressier occasions because I have limited space in my closet and try to make the most of my investments. I keep my shoes for a long time, so I don’t mind splurging on quality pieces that I know will last. I only buy one or two pairs each season, so I’m very selective.
If I had to pick my favorite fall shoe, it would definitely be the bootie. I’ve had my classic black pair for about three years now, and they’re still going strong. Last year, I added a light tan pair to my collection because I was reaching for them almost daily. These booties go with everything—Skirts, trousers, Jeans—and they’re surprisingly comfortable. Rachel Comey really set the standard for booties with her Mars design, which remains the best in my opinion. But Madewell and J. Crew also offer great alternatives that are both stylish and budget-friendly. Honestly, Madewell has become my go-to for reasonably priced, high-quality footwear.
As someone who leans toward a tailored aesthetic, brogues are another must-have in my wardrobe. I’ve always appreciated their timeless appeal, and they look fantastic with almost any outfit. While shopping with Todd last summer, I almost picked up a pair of Allen Edmonds, but I held off. This fall, however, I finally caved and got myself a pair. To my surprise, they’re incredibly comfortable and versatile—they look just as good with my worn-in jeans as they do with my culottes or long skirts. They even pair beautifully with skinny pants, wide-leg trousers, and pencil skirts.
Moving on to loafers and flats, I’m currently drawn to styles that add a touch of sparkle or embellishment. It’s amazing how these small details can elevate a simple flat into something special. I find them surprisingly versatile and fun to wear.
When I’m done walking all day, I usually switch to something a bit dressier once I arrive at my destination, especially if I’m heading to the office. Classic black pumps and nude pumps are staples in my wardrobe, though I personally prefer my nude pumps to have a hint of pink. Variety keeps things interesting, so I like to mix things up with pumps that have a unique twist.
I may be one of the few people in the U.S. who doesn’t embrace sneakers and Sweatpants as part of everyday attire. For me, they’re strictly workout gear, and I rarely find myself in situations where I’d wear them unless I was jogging or working long hours on my feet. That said, if I were to break the rule, it would probably be for these particular sneakers.
What about you? Your choices might vary depending on where you live. Are there any specific shoes you’re eyeing this fall?
P.S. If you’re curious about my shoe picks, you can check out my Accessories I Love Pinterest board!
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