Dr. Martens are steeped in a traditional rebel spirit. Sure they were designed as work boots but quickly counter culture adopted them as part of their uniform. I have worn Dr. Martens throughout my life and even though I am over 50, I don’t plan on giving up on them any time soon. Honestly, you can wear Dr. Martens at any age!
My First Pair of Dr. Martens
I went to a private school in the 1980s. We were required to wear the ugliest plaid, first jumpers (elementary school), and then skirts (middle school). We tried everything to express our individuality. First, we started with big jewelry when we received little pushback; we moved on to safety pins pinned on our skirts. Apparently, that was too far, and the school forbid all inanimate objects on our persons and even banned earrings that hung 1/2 inch below our ear. All we had left to express our individuality was our shoes.
So long as the shoes were closed-toed and functional (i.e., not high heeled), we were allowed to wear what we wanted. Of course, the coolest shoes to sport were Dr. Martens, which my parents refused to buy because they felt they were way too expensive. I purchased my first pair of Docs with my own money from my first job at McConnell’s Ice Cream Parlor. For the better part of almost forty years, they have been a staple of my closet.
My Daughter and I Both Wear Docs
When my daughter was in middle school, she asked for a pair of Dr. Martens. Cami benefits from the fact that I have fashion trauma from my childhood, and she can usually convince me to get her almost anything she wants. I know. I am likely causing her fashion trauma, which will manifest in some other type of neurosis, but I am happy to have someone share my love of fashion.
Doc’s In My Closet Now
Currently, I have three pairs of Dr. Martens in my closet. I recently picked up the Leona Boots, a modern version in Oxblood. I like the chunky sole. A great pull-on pair in faux snake and a pair of slide sandals, which I didn’t get to wear last year because of the stingray incident but will wear in heavy rotation this summer.
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How to Wear Dr. Martens
Dr. Martens Outfit 1: Wear with a Floral Dress
I am a fan of the push and pull of edgy pieces combined with more feminine pieces. It is this yin/yang that works so well in building outfits. Pick your favorite floral maxi dress and pair it with your boots. The effect is effortlessly cool. Add a denim or leather jacket for warmth, and you are ready for almost anything. I’m wearing the Rare Feeling Maxi Dress by Free People. It is available in five fabulous colors, and I am wearing a medium for reference.
Maxi Dress Picks
Dr. Martens Outfit 2: Wear with a Short Dress + Denim Jacket
Doc’s look just as good with your favorite mini dress. I wear this combo all summer and into fall except for the hottest months, which in So Cal are Aug. & Sept. This is a comfortable length for a short dress for me, but the shorter you go, the better the combination looks. Of course, my daughter takes this a little too far sometimes, and I tell her she needs to swap out for a longer skirt. If you can’t bend over comfortably, it is a “no go” in my books.
My dress is James Perse from last season, but this Fresco Knit Dress is similar. The jacket is from Madewell. Dr. Martens looks good with any mini dress style so long as the hem is above the knee. Wear the boots with your favorite floral, denim, baby doll, or body con mini dress.
Mini Dress Picks
Dr. Martens Outfit 3: Wear with Oversized Sweater + Skinny Jeans
This outfit is a no-brainer. Pair your Docs with your favorite denim. Add an oversized sweater, and you are good to go. I am wearing skinny jeans and the wildly popular Free People Easy Street Tunic. This versatile sweater comes in thirteen colors and consistently sells out. I love it so much; I have it in four different colors. It washes well and doesn’t wrinkle. It has an oversized fit that isn’t bulky.
Dr. Martens Outfit 4: Wear with Chinos + Striped Top + Utility Jacket
My favorite chinos are the AG Caden Crop Twill trousers. They are the perfect weight for spring & summer. They come in many different colors, including camo, and you know how I love camo. These pants travel well and are beyond comfortable.
Add your favorite tee and a utility jacket for a casual Saturday look. Utility jackets are the perfect summer accessory. I have one with me at all times. They are perfect for throwing on when the AC inside gets too cold, which seems to happen all summer long.
This jacket is from Madewell. They have updated it, and it is available in black too.
Dr. Martens Outfit 5: Wear with Jeans + Blazer
This Oversized Blazer from Everlane is one of my favorite purchases from 2019. It is currently unavailable, but I suspect it will be back for fall. Blazers are still having a major moment, and the trend won’t be fading any time soon. For summer, Everlane has a Cotton Linen Blazer with a similar oversized fit to mine. It is available in six colors. The dusty blue is so pretty.
Mix up your skinny jeans with a modern color like this distressed grey. A stone-washed black pair of skinny jeans would also look amazing.
Oversized Blazer Picks
History Repeating Itself
My kids are now in a private school with uniforms. Last year they banned skirts for the girls because it became impossible to police the skirt lengths. Or so they say. It was a big brouhaha at the beginning of the year but slowly, the students adjusted to wearing tan, black, or blue pants. Shoes are still an important part of individuality anytime you have to wear a uniform.
Every time my daughter pulls out her Dr. Martens, I smile. Of course, my kids always complain about the uniforms. Right now, I bet they would gladly wear a uniform if they could just get back to the physical campus and see their friends. Even with so many things changing, some things don’t seem to change: shoes make an outfit, and Docs are just cool!
I would love it if you followed me on Instagram for my everyday outfits or on Pinterest for my fashion inspiration. StyleDahlia is for fashion-minded women in the prime of their life. We delight in the beauty of every day, and we hope you will join us on our journey. Happy Shopping, Dahlias. xoxo
