The Cutest Boots

If there is one kind of shoe that I could talk about forever, it would be riding boots. I’m still working on going through all my shoes right now and inspected my riding boots to see if they needed a trip to the cobbler before it cools off. (Please note: it has been extremely hot this week here in the city and I’m hoping that means we’ll have an extended summer, just like I wished for!)
My boots are in great shape (the Tory Boots are made to last!!!), but I kind of wish I could go boot shopping again. I think I’ll have to settle for sharing my favorite pairs with you in hopes that I can live vicariously through your boot shopping. I prefer a boot that hits below the knee and there is no shortage on cute styles. 
(One random side note/story: In elementary school, one of my recital dances was to the song “These Boots Are Made for Walkin’.” We wore these white gogo “boots” slipped over our jazz shoes…. mine were too big and kept slipping off during the rehearsals. I was yelled at for tugging at them and someone’s mom ended up gluing the boot to my jazz shoe and leg with hairspray. To this day, hearing that song makes me feel like I have a knot in my stomach from worrying about my dumb boots slipping off!)

Shop more these plus a couple extra favorites below:

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Do you have a favorite pair? Which would you pick?

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Your timing on this is perfect — totally going boot shopping today! I think the Penny Boot is my favorite of these.

I'm also glad to hear that I wasn't the only one subjected to These Boots Are Made For Walking as a dance recital song. I think mine was for acrobatics but I've mostly blocked it out, except that at one point we were on our backs with our feet in the air.


I find it out of touch with your reader base that you didn't include any cheaper options. The majority of post grads and college students don't have the money to drop $180+ on riding boots. Any affordable boot suggestions?


True, but a great pair of riding boots is an investment because they'll last forever! For the past five years I've spent $30-$40 on pairs of boots that I've had to toss after a semester, I could have bought one good pair that I would still have now. But I suppose it all depends on whether or not you would want to spend the cash on that one pair upfront!


Vanessa Rose Lang

Love the Cole Haan! Just some advice though, Tory Burch boots run VERY tight in the calves. I'm average height/weight and couldn't get them to zip more than half way! If you're considering them try them on at a store as opposed to ordering online.