Maxi Dress with Dr. Marten Leona Boot

How to Dress Up Doc Martens

Hi, friends! I’m back on the blog today to share three different pairs of Doc Martens and three elevated outfits to wear them with! I’ve shared Docs on my blog so many times before, and that’s because they’re a wardrobe staple! More often than not, I’ve found that people think Doc Martens are ONLY edgy/casual and can’t be dressed up.

I’m here to prove you wrong!

Doc Martens have been my go-to boot style since I was a junior in high school. And truthfully, I don’t think you could go wrong adding them to your wardrobe.

Let’s get started!

Maxi Dress + Cropped Jacket + Dr. Martens LEONA Boot in Chestnut

Maxi Dress with Dr. Marten Leona Boot

This Free People maxi dress is always on repeat for me during the spring and summer months. I found it on the one-of-a-kind rack and it almost feels like it was made for me! I love that it has short sleeves and a full, yet flowy skirt.

Pairing the Leona boot with this dress is a great example of high-low styling. The Leona is a bit more elevated than other pairs of Docs simply because it has a 2-1/4″ heel. When I wear these boots, I’m over 6′ tall, so they definitely give a solid lift, which elevates any dress or skirt. Plus—if you hate wearing heels like I do, this is the ideal alternative for you!

Midi Dress + Sweater + Dr. Martens LEONA Boot in Bone

Midi Dress with Dr. Martens Leona Boot

The Leona boot makes another appearance! This is most definitely my favorite style of boot—clearly why I have two of the exact same pairs. What can I say—when I find something I like, I need more than one! I wish the Bone color of these boots was still available, but they recently released them in Sand.

This might just be personal taste, but I think the best way to make a pair of Dr. Martens look more elevated is to wear them with something flowy. The combat-inspired style of Docs needs to be softened, and loose, flowy clothes are the exact opposite in terms of style!

Mini Skirt + Long-Sleeve Thermal + Dr. Martens Rometty Boot

Mini Skirt with Dr. Martens Rometty Boot

The Rometty boot is a great balance of the femininity and the tough, which I think is why I love them so much! I’ve paired these boots with so many skirts in my wardrobe, so it should come as no surprise that I chose a skirt for today’s look! I found this skirt in the sale section at Anthropologie. The olive color is the perfect neutral for me. It pairs well with just about anything, but it’s not as boring as white, black, or khaki!

I paired the skirt with my favorite thermal from Caite & Kyla. I absolutely love the hand-embroidered details! Of all the outfits I shared in today’s post, I definitely think that this one is the most casual. However, a simple pair of black Docs is a great introductory pair to get to know the brand!

Check out my Instagram Reels for more styling tips!

Well, that’s all I have for you today!

I’ll be back on the blog again next week with a new post!

Until next time!


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