How to Style Dr. Martens

Hi, friends! Welcome back to Stylishly Good Vibes! Today’s blog post is all about my favorite brand of shoes: Dr. Martens! I’ve been wearing Docs for almost ten years, so needless to say, I definitely know how to style them. I always get a lot of questions about my Docs when I wear them, so I figured why not make a post about it!

Let’s get started!

When I was first introduced to Dr. Martens while I was in high school, I thought they were the coolest. But, I wasn’t sure if I could pull them off, ya know? They give off a very specific look, which I think tends to scare people away from wearing them. The thing I love most about Docs is that people either like them or hate them. There’s no in between! I have friends who absolutely hate them, which is fine! I’m still going to wear them every day with pride LOL!

Anyways, my Docs are a part of my style story—plus they are the most comfortable shoes I own. That’s another big misconception that I hear about Docs. A lot of people think that because of their construction, they take a minute to break in. But, I assure you—they don’t. If anything, my Dr. Marten sandals took the longest to break in, but that was probably just three wears.

First let me start with some background about the company! Dr. Martens was founded in 1901 by the Griggs family in a small town in England. But it wasn’t until 1947 that the air-cushioned Dr. Martens we all know and love began production. Known as a “rebellious form of self-expression,” Dr. Martens will always be my favorite way to express myself through footwear.

How to Style the Leona Boot

I have two pairs of the Leona boot from Dr. Marten. One is in the color bone and the other in chestnut. I bought the bone ones first, loved them so much that I felt I needed to get them in brown. Honestly, I’ll probably buy the black pair, too, but for now I’m content with these ones!

These boots provide a definite LIFT without being hard to walk in. When I wear these, they give me a solid 3 inches on top of my current height. So basically I’m a walking Gumby when I wear these. I tower over the majority of people, which is fine by me!

Of all my Dr. Martens, I think these are my favorite to style—and the easiest. To me, they look a little more elevated and refined than my other pairs, which is why you can catch me wearing both pairs to the office on the regular!

I love styling these Dr. Martens with crew socks and a skirt or dress. It’s the perfect high-low styling example. I think if you’re looking for a more feminine twist on the Dr. Marten boot, get yourself a pair of Leona’s. You will wear them all the time, trust me!

How to Style the Rometty

Of my six pairs of Dr. Martens, these ones are definitely my edgiest pair. I don’t have tons of black shoes, which is one of the reason why I bought this pair. One of my friends and I actually have the same pair, so they must be good!

The Rometty is comparable to a Chelsea boot with a lift. I would say that in terms of lift, this style is similar to the Leona boot I mentioned above. They have more of a matte black leather finish, which I really love. I always pair these boots with a fun pair of socks to brighten them up.

However, for today’s outfit I wanted to show one of my favorite outfits to wear with the Rometty. I think this outfit is pretty edgy, which pairs well with these boots. But, if you’re not looking for an edgy look with your boots, I wear the Rometty with dresses and skirts all the time. This pair is definitely more of a winter and fall boot for me, but I love them just the same.

Wear the Rometty Dr. Marten boot with dark wash skinny jeans, patterned pants, midi skirts, dresses.

The Classic Dr. Marten Patterned Boot

This is one of my first three pairs of Dr. Martens. I’ve had these for almost six years now and they’re still kicking it! What initially attracted my attention to Dr. Martens was their patterned boots. I love the pattern on this pair because if you look closely, there are funny little doodles all over them. So unexpected and cool!

The patterned Dr. Martens are most notably the pairs that you will instantly know are Docs when you see them. I think everyone should try to have one fun patterned pair of Docs for those days when you’re trying to be really rebellious!

I love that they are a white base with blue detailing because it means I can pair them with just about anything. These boots are one of my go-tos on a day off because they attract attention, which is fun with personal style. Not sure about you, but I love when people spark up conversations with me about personal style. This pair of Docs is definitely a conversation starter, so be ready for that when you get your own pair!

I’ve had a lot of friends tell me that they wish they could pull off Docs, but they think they’re just too chunky for them. Trust me, with the right styling, your Docs can look super fly!

For the patterned Docs, I love to wear them with a light-wash skinny or boyfriend jean, or a dark denim. I don’t know why, but I really enjoy wearing this particular style with pants. They’re a little bit lower in height, which I think looks better with pants rather than a dress, but that’s just personal preference. If you wanted, you could easily wear these with a fit and flare style dress, or a midi skirt.

Well, that’s all I have for ya. How to Style Dr. Martens, aka my favorite shoes ever!

Until next time!


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