It takes an effortlessly cool chick to pull off track pants and knee-high cowboy boots. That's why I wasn't at all surprised when I shared Kendall Jenner's look with Fashion Director Hannah McKinley [1], giddy with excitement about it, and she said, "I feel like it's very Diana [2]." (That's how we refer to Princess Diana around here, FYI.)
"YES!" I thought, wildly fired up as I searched for this iconic image of the late royal from 1989, dropping her sons off at Wetherby School. BTW, what mom pulls this outfit off successfully in the drop-off line outside her vehicle? If I was wearing this combination, I think most people would assume I had just finished shoveling an entire box of dry cereal in my mouth. Also, obviously, there would be crumbs on my white sweats.
And really, leave it to Kendall to re-create Diana's magic (perhaps unknowingly) 30 years later [3] with Adidas slacks and a hunter crewneck, when cowboy boots are as ordinary as sneakers and Princess Diana's '80s influence [4] is palpable on virtually every runway. We aren't even mad at Kendall for forgetting the blazer and baseball cap; we just hope she realizes she was channeling the most stylish British royal [5] in all the land when she stepped into that LA sunlight.
Princess Diana Wearing Cowboy Boots and Sweats in London in 1989
Kendall Jenner Wearing Cowboy Boots and Track Pants in LA in 2019
Shop the Look
Adidas SPZL Harpurhey Track Pant [7] ($85, originally $135)
Tibi Snapped Track Pants
Tibi Snapped Track Pants [8] ($197, originally $395)
Asos Design Curve Track Pants With Studded Side Tape
Asos Design Curve Track Pants With Studded Side Tape [9] ($20, originally $45)
Reformation Hunter Sweatshirt
Reformation Hunter Sweatshirt [10] ($58)
Boohoo Oversized Sweat
Boohoo Plus Oversized Sweat [11] ($15, originally $30)
Levi's Premium Vintage Clothing Bay Meadows Sweatshirt
Levi's Premium Vintage Clothing Bay Meadows Sweatshirt [12] ($114, originally $165)
LANE BOOTS Robin Western Boot
LANE BOOTS Robin Western Boot [13] ($427)
Lucchese High Noon Western Boot
Lucchese High Noon Western Boot [14] ($498)
Jeffrey Campbell Calvera Knee-High Boot
Jeffrey Campbell Calvera Knee-High Boot [15] ($260)