Over 50 & OTK Boots

img_0186Over 50 and Over-The-Knee Boots? Yes, you can! The OTK Boot has become an accessory that should find its place into every wardrobe — no matter your personal style or age. Since the trend took hold, I’ve added 4 pairs to my wardrobe. My oldest pair is up at our cabin, while the other 3 are in regular rotation in my fall/winter JC/NYC wardrobe. All are Stuart Weitzman, who’s the King of the OTK Boot as far as I’m concerned. While his boots (and shoes) are not cheap, they truly are investment dressing. If well maintained with water/stain protector and professional cleaning and repair, you will have them for many (many!) years to come.

Here are a few OTK style principles I adhere to:

  1. Stick with a lower or block heel. While the sky high styles look amazing, they are not for me. Or my feet. Or back.
  2. Choose a neutral color: black (duh!), navy, brown (in all its hues from taupe to chocolate) and grey are my go-tos.
  3. When wearing a dress, I’ll match the shade of my tights to the boots (or as close as possible) for a seamless, leg-lengthening look. Skinnies in dark hues are my choice when it comes to jeans.
  4. Don’t be afraid! These boots flatter everyone by elongating and slimming the leg, while adding a touch of sleek chic to any look. They are so comfortable to wear and walk in. And many of SW’s styles (like the 5050 in these photos) combine leather or suede with stretchy micro, so they will fit almost every calf size.


This first OTK look features my chocolate brown 5050s. I pretty much could not imagine winter life without them. My high waist skinnies (ahhhh!) are in the darkest wash I own, which means they go with everything. I love the fringed hem on this marled wool sweater, along with its easy fit and longer tunic length. Cozy, comfy and camouflage for those not-feeling-so-slim days. For added warmth a fur vest (or faux) is the perfect layering piece. This one even has a head-warming hood. My accessories are vintage: a leather and wood Raggedy Ann necklace that was hand-carved-and-crafted in Nicaragua for my Mother as a child and a mint-condition Coach mini tote I found at Antique & Variety Mall in Plattsburgh NY. Plus my water-resistant suede motorcycle cap which is perfect for need-a-haircut-so-bad days! ) (New haircut coming in next post!)

Boots: Stuart Weitzman 5050 but more affordable here and here

Sweater: Ann Taylor (50% OFF!)

Jeans: J Brand (a favorite), limited sizes in this style but LOTS (on sale!) to choose from here (outnet.com is one of my absolute favorite sites!)

Vest: (scored at Century 21, old) similar here and here

Cap: Tracy Watts New York (old) but all their hats are amazing! Similar caps here and here

All photos by Chris & MP Allegaert on iPhone 6.

3 thoughts on “Over 50 & OTK Boots

  1. Really like this post! I got my first pair of OTKs recently. At 60, I was a bit worried about “age appropriateness,” then thought, “what the heck!” Actually, what really happened was I ordered the wrong pair of boots and then when I tried them, I decided I really liked them! I wear them with leggings, riding skirts, and column dresses. Every time I wear them, someone asks me about them–you are right on target, the right boot does wonders for an outfit!

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