Can I Get Away With Wearing Doc Martens? (Ask A Question)

doc martens floral

Photo from Pinterest – Danielle Rogers


Hi Joanne,

I’m a 36 year old woman, and I love boots. I wear riding boots and cowboy boots, a lot. I even kept my Dr. Marten boots from when I was a teenager. Do you think at my age I could get away with wearing them still, and if so what should I wear them with?



Hi Angela,

Thanks for checking out my blog, and great question! I love boots too, but Dr. Martens are definitely a trendy boot only teens and 20 year olds can get away with. Although I’ve heard they’re very comfy, Dr. Martens are unflattering boots – very clunky and rugged. Wearing short boots like Dr. Martens give the illusion that your legs are shorter and stumpier than they are because it cuts the visual line down your leg (see the picture of Jessica Alba below). The goal when dressing is to look long and lean – “putting your best foot forward” even if you’re not a super model (believe me, I’m no supermodel!). Nothing ages you quicker than wearing something that isn’t age appropriate – it gives that image that you’re trying too hard. Better to dress the best you!

Riding boots are definitely in this fall and winter season, so be sure to rock your riding boots! There are so many ways to wear riding boots, but it’s simpler than you might think. They’re very versatile so you can wear riding boots with many outfits. Though make sure to wear super skinny jeans or leggings if you’re tucking your pants into your boots (see blog post here).

Easiest way to put together an outfit is this:

top + skinny jeans/leggings + riding boots = great outfit :)


Jessica Alba is a naturally tall and lean woman, standing at 5′ 7″ but her legs look a bit short and stumpy in a pair of Dr. Martens.

dr martens outfit

Photo from Pinterest – Jelkje Bergsma


If you like boots, wear a pair of riding boots. The flat boots are just as comfy as a pair of Dr. Martens, yet look much more stylish.

cute riding boot outfit

Photo from Victoria Secret

For some riding boot outfit ideas, check out this blog post here.

Let me know if you have more questions. I’m more than happy to answer them.

Happy Holidays!
Joanne :)