How To Style Dr. Martens

I know! I know! I know the answer to this! How do you style Dr. Martens? However, the hell you want to. Thanks for coming. Bye.

No, but really there isn’t a brand out there that has always let you be exactly who you are and the style freedom to wear these trusty boots however you damn well feel like. There isn’t. Yes, thanks to the pandapoca (pandemic / apocalypse also known as Covid Lockdown) of 2020, 2021 and well 2022 did we see a lot more anything goes style but nothing like what Docs has done their whole existence. Effortlessly.

FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point. Also, assume links that take you off the site are affiliate links such as links to Amazon. this means we may earn a commission if you buy something.

I wear them you wear them we all wear them!

What is one thing I always have to shout out about style? That most of the true fashion staples all come out of necessity as well as a utilitarian function, nothing different about this story. They were originally worn by the British working class and Postal Service and it ain’t got nothing to do with the term going postal. Calm down Karen the manager is on the way! The point is that they didn’t start off as being anything more than a really durable boot for really hard-working people ya know the blue-collar dudes and then maybe the skinheads started wearing them. Hmmm did the blue-collar workers turn into skinheads or did the skinheads work by day as the blue-collar dudes or maybe it’s nothing of the sorts at all and they are completely unrelated. Just a thought and a hard habit to break after spending years and years trying to analyze those Karens. Anyway, the rest is all history and the marriage of music royalty and DMs as in Dr. Martens not as slide in all began when Pete Townshend of The Who started wearing them on stage and doing his cute little bunny hops. Makes sense they are known for having bouncing soles ha ha. It feels like every “IT” artist of any genre of music has adopted the boot into their wardrobe.

Walk like a Brit.

When the boot first came off the production line apparently the sold for roughly 2 pounds, that’s about the equivalent to 65 bucks today so in perspective that’s a great deal. You can’t get anything near a Doc quality boot in this day and age for 65 bucks! Get the appeal? I mean their construction and quality of leather makes them the boots of all boots, so I get people’s obsession.

If you ever get a chance to watch a pair of Made in England boots, be made do it, it’s certainly impressive. I mean from the melting of the PVC outsole to cutting of the leather, the stitching of the welt, punching of the eyelets, pulling off the last, embossing and the melting of the upper to the outsole and you thought your dating situation was complicated. Just like anything the complexity of this creation is part of its rebellion appeal. There is no other brand with this type of construction.

Ok, ok I get it enough already with the walk down memory lane.

You’ve come a long way baby.

Listen, I tell no lies when I say that navigating through styling my first pair of Dr. Martens wasn’t the easiest especially if you have typically been into the super femme silhouettes. They can feel a little bulky and a lot of heavy, but they are sneaky because once you get it worked in that all goes away and then you’re left with just the perfect comfortable boot. You have to stick with it though because it takes about 2 weeks and some Band-Aids to get to that point.

I stand by the fact that there isn’t really a wrong way to style these icons but here are some of my favorite ways.

I love a good drama piece of clothing mixed with some special classics. I mean yeah this is a heeled boot but it’s pretty much just the elevated version of that classic 1460 8 eye sans yellow stitch and with black patent.  This is actually a good business casual look for a Friday and then an easy stroll right into Happy Hour and if you can handle it right on into the night vibes.  Get home and rip those babies off and it’s all good.

Ya know sometimes it’s not even what you where with them it’s as simple as how you wear them.  Again another rarity when it comes to rocking your docs, you don’t have to tie your laces.  I’m pretty sure this started by the good ole break in but there is something about this look that just works.  It doesn’t matter if you are just slipping your paws right in there and leaving those string failing or you tidy them up and a bit more contrived.  It’s cool kid status.

Hands down my favorite will always be docs and dresses, dresses and docs.  True Love Forever!  I love long dresses or short dresses but since I’m a total Gen-Xer the babydoll dress for me is the ultimate.  Thank you fashion Gods for bringing them back.  Takes me right back to my San Francisco rave days.  Ravers always wore their docs and especially in all the colors if you had that kinda cash at that age.  Or if you were like me, you scored a 2nd hand pair and honestly that was almost better they fit perfectly.  For the most part I assume that when people want to know about Dr. Martens I assume they are all referring to that boot.  1460.  Did you know the name comes from the day it first rolled off the production line?  April 1, 1960 but it’s British so hence 1460.

I think one of the funnest ways to style your Docs is by picking up a pair of their florals and play around with the laces like this pair of Sinclairs.  Uh they are known for creating their own signature prints and it’s almost a cult like following to add the latest to your collection.   I’m serious I’ve seen some of those fast fashion brands try to knock the prints off, next thing you know there is pants, dresses and tops in that new DM print.  If you’ve ever worn a pair they just make you smile when you look down and see them.  Shoes are meant to be fun. Whether it’s a boot or shoe they are both great and a great way to spring into new seasons.

You can look up how to lace your Docs and there are a ton of ways to get creative!  It’s an art!

I am a fan of bells and whistles.  Sometimes it can be as simple as your socks or tights and nothing is more perfect than pairing it with a pair of Mary Janes.  They aren’t for just school girls anymore!  

I mean there are so many ways to style this classic must have footwear.  The beauty is that there are so many options!  It’s not just about this leather boot anymore.  They have lightweight canvas and athletic options, kids footwear that matches the adults so maybe the theme of the day is mini me.  I love that they have a vegan line so you can get the iconic look if you are into that!  Don’t forget that they are an artists dream, if you’re into customizing grab your art supplies and get busy! 

Honestly you can’t fail here.  They are on feet from runways of fashion houses to runways of planes.  You can work your look like Bella Hadid or  wear them on your wedding day (that’s a real thing).  That’s the beauty of the brand.  You can be unapologetically YOU.