I loved this slideshow of author Stephanie LaCava’s favorite New York haunts. I totally nodded my head when she said, “I sort of always wear the same things, though in different ways.” Isn’t that the definition of classic style?! Some of her outfits were a little edgier than my go-to looks but this one stopped me in my tracks:

Comfy sweater for winter warmth? Check. Skinny jeans and killer heels? Check, check. But it’s the classic tote that gets me. Preppy can be completely modern and this look is proof. Just don’t be surprised when you see me in ten different versions of it these next few months 😉

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22 thoughts on “HEAD OVER HEELS.

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  1. i wear basically the same things or colors every day. it makes life much simpler and i generally look put together. i really want a classic tote though. rory would look so cute in that lands end one!

  2. Oooh, I love this! You’re so right, there are way more interpretations of preppy than people often think, and this is the perfect example!

  3. I’ve had my eye on those booties for a while…!

    My go to winter look is similar – skinny jeans, the world’s most comfortable motorcycle boots, big sweater, fun scarf.

    Some may call it lazy, I call it a uniform.

  4. Adorable! Sadly, my beloved Land’s End tote of 5 or 6 years has seen better days…from what I’ve observed, the ones from L.L. Bean are similarly priced and seem much more durable–they literally feel like sailcloth, probably because that’s what they’re made of!