Peter Macfarlane reviews the Oboz Sypes Mid Leather Waterproof shoe as a higher cut alternative.

The Oboz Sypes Mid Leather Waterproof is a slightly higher version of the Low, and therefore an interesting comparison with the other shoes in this test.

Peter Macfarlane recommends

The Sypes Mid are about as close to a trail shoe feel as I have found in a boot format, so they could be a good middle ground for those who struggle with the more open fit of trail shoes but still wan
Pros
  • comfort
  • grip in most conditions
  • trail shoe feel with higher cuff
Cons
  • grip not great on wet, hard surfaces
  • price
Quick specs
Price: $165 / £165 (available from Zappos)
Weight: 934g pair, UK9
Materials: Waterproof nubuck leather, 100% Recycled Polyester Laces, 100% Recycled Polyester Webbing.
Features: Trail Tread outsole, Bend midsole, O Fit insole
Waterproof? B-Dry liner
Sizes: UK 6 to 12 inc half sizes from 6.5 to 10.5
Woman’s version? Yes
obozfootwear.com

It has a nubuck leather upper leather upper with synthetic heel reinforcement and a thick plastic toe bumper where is also a double layer of nubuck. The outsole has quite aggressive lugs which grip well in most conditions although they do tend to slip a little on steep or wet ground (I have worked around this with more sideways foot placements on steeper downhills).

The laces run through simple punched holes in the nubuck, and while the leather has stretched a little there are no worrying signs of wear. At the cuff the laces run through 2 metal hooks, which is where the more boot-like feel comes from. This higher ankle cuff consists almost entirely of padding and mesh and does not inhibit ankle movement, which means the Mid feels very similar to a low-cut trail shoe.

There is enough padding under the tongue that I haven’t had any issues with lace pressure, and the fit is good with a neat supportive heel cup and enough room at the forefoot for my toes to spread a little. There is a proprietary waterproof lining which, alongside the higher ankle makes the Sypes a good wet weather choice if using without gaiters.

Midsole cushioning is good and there is a very soft and pleasant flex at the forefoot. The Sypes Mid are about as close to a trail shoe feel as I have found in a boot format, so they could be a good middle ground for those who struggle with the more open fit of trail shoes but still want the flexibility.

Testing conditions

Peter walked Munros and ran his local trails in the Kilpatrick Hills for this test and is a long term fan of trail shoes for general outdoor use. He is a UK9, has a narrow heel and wide forefoot, and the weights are taken from his own digital scales.

This review was first published in the June 2025 issue of The Great Outdoors magazine.