Like any good Millennial (or Gen X’er, for that matter) my relationship with Dr. Martens goes wayyyy back to the ’90s. They were a part of my “fashion awakening” if you will. I saw all my favorite style icons (mostly on TV) sporting Docs with everything. I was a little too young to embrace that trend the first time around but I’m making up for lost time now. Also, who can forget that period of time when Dr. Martens leather sandals were the ‘it’ sandal (or maybe that was a just a West Texas thing)?
IMO, if you’re looking for chic, timeless leather boots, there is no better way to make a statement than with some iconic Doc Martens. The leather quality is superior and so is the comfort level. Let’s get into why I’ve been wearing my Leona Dr. Martens non-stop this fall and winter.
Leona Docs (7)
Where To Buy Doc Martens Leona Boots
Nordstrom | Amazon | Zappos | Doc Martens | Free People | Nordstrom Rack
There’s no denying that Doc Martens have a serious cool girl factor — they have a special way of expressing individualism when you wear them. Did you know this brand has been around since 1901?! Their beginnings started way back with the Griggs Family in Northamptonshire in the English Midlands and they’ve been building their legendary brand since. I love how their company still stands for quality, sustainability, and timelessness all these years later. They are truly a brand you can feel good getting behind and putting your foot into.
Why Docs Are Great For Winter
Living in Michigan, I can easily say I have a love/hate relationship with winter and all of winter wear, for that matter. Out of my natural Taurus stubbornness, I’ve had a hard time submitting to wearing more traditional winter boots, like a pair of LL Bean duck boots or Sorels. I still want to try and make a statement, even in winter, and that is exactly where I’ve found Dr Martens to fit into the picture.
The Leona boots have a solid and durable sole, that’s still flexible. The high-quality rubber allows for the right amount of give when walking, with extra ridges for traction. The leather is top-notch quality — it feels soft and in no need of breaking in, yet somehow it always stays clean and doesn’t absorb snow/salt despite my daily wear during Michigan’s snowy winters.
Sweater (M) | Similar Levi’s (28) | Docs (7)
How To Get The Right Size: Dr. Martens Sizing Notes
There are two things you need to keep in mind when buying Dr. Martens; Firstly, they run large. And secondly, they don’t do half-sizes. I made the mistake of ordering up a size (I am usually a size 7.5) but quickly realized the error of my ways and returned for the size 7 which fit perfectly. Obviously, the leather will soften and stretch a little bit over time but so far that has been minimal for me.
How I’m Styling My Doc Martens for Winter
The better question might be: How am I not styling these Leona Dr Martens for winter? Because I have been determined to make these boots work with as much as possible in my closet this winter. If there’s a chance I think these boots might look cute with what I’m wearing, then I’m going for it! That means I’m wearing them with camo pants, jeans, skirts and tights, and yes — even a few dresses.
I realize that going with the brown leather option was a ‘choice’ but I am so glad I chose this color instead of black. I think the rich, warm brown color adds a unique layer of interest that the black doesn’t. The brown leather also highlights the antique details (like the brass eyelets) as well as emphasizes the small raised heel on these particular Leona boots.
Outfit 1: Fair Isle Knitwear + Vintage Camo Pants + Leona Dr Martens
Similar Sweater | Similar Pants | Docs (7)
This is my favorite ‘go-to’ outfit of the moment. I love the fun-ness of mixing the camo print with a chunky fair-isle knit and I give my pants a slight cuff to give a better peak at the boots. I also decided that this outfit looks better with my hair down, otherwise it looks like I came from Army basic training camp.
Outfit 2: Mango Layered Mock Neck Sweater + High Rise Ankle Cropped Slim Jeans + Leona Dr Martens
Sweater (M) | Similar Jeans | Docs (7)
I’m about 50/50 on keeping this Mango sweater. I thought it was a kinda cool, and also an interesting idea for a sweater – but then I’m also worried it looks like I’m trying to look like a ‘teenager,’ which…..gives me pause as a 40-year-old woman. But the quality of the knit is decent, and it’s not itchy. So… I’m a little torn and I’ve been wearing it around with some older black slim leg jeans I pulled out of the closet.
Outfit 3: Fun Floral Cardigan + Free People Moxie Jeans + Leona Dr Martens
Sweater (M) | Jeans (28) More Sizes: Free People | Amazon | Bloomingdale’s | Docs (7)
I’ll admit I had a bit of a messy vibe going on this day, but was hoping my super cute (and soft) floral cardigan distracted from my need to iron my jeans. I picked up this cardigan in black also because it made me happy and it’s also super soft and affordable. As always, Free People’s Moxie jeans are a must-have in my weekly closet. They look especially good cuffed with these Dr. Martens.
Outfit 4: Free People Oversized Sweater + Loft Plaid Wrap Skirt + Tights + Leona Dr Martens
Sweater (M) | Skirt (6) | Tights | Docs (7)
This was my favorite ‘go-to’ outfit over the holiday season. I wore it more than once over Christmas. This Free People oversized Heart You sweater is a little bit more expensive than I usually go for but it is exactly what I have been looking for for YEARS. I found it on sale right now at Nordstrom Rack. And this cute little red fringe wrap skirt is currently on sale for under $35 at Loft. I also have my eye on this camel colored Rails Wool Wrap Mini skirt too.
Outfit 5: Mango Wrap Sweater + Pilcro Mid-Rise Relaxed Jeans + Leona Dr Martens
Sweater (M) | Jeans (28) | Docs (7)
This is another one of my favorite everyday outfits. All together this outfit is exactly what I hoped it would be: cozy, comfy and chic. I highly recommend both these top-rated bestselling Pilcro jeans (I have the Lonnie Wash) and this Mango Wrap Sweater that I love so much I’m thinking of getting in brown, too.
Outfit 6: Gap Fair Isle Cardigan + Gap High Rise 70’s Flares + Leona Dr. Martens
Cardigan (M) | Similar Cardigan | Jeans (27) | Boots (7)
Unfortunately, this cute lil’ red fair isle cardigan from Gap keeps selling out, but I keep linking to it in case they decide to restock it (because with Gap, you never know). J.Crew has a cashmere option with a similar vibe and I also love this Favorite Daughter option. As for the jeans…trust me, you need them. Shana and Em are fans too. This is the second pair of these Gap High Rise 70’s jeans that I own. They are super flattering and just as comfortable.
Outfit 7: Gap’s Velvet Floral Mini Dress + Layered White Tee + Tights + Leona Dr Martens
Dress (6) | Similar Top | Tights | Boots (7)
This cutie of a velvet burnout dress is from Gap and is currently an extra 50% off at checkout. It also comes in a lovely burgundy color. This entire outfit is very ‘Clarissa Explains It All’ coded. For the girlies, who get it. 😉
Outfit 8: Free People’s Heart You Oversized Sweater + Levi Black Jeans + Leona Dr Martens
Sweater (M) | Jeans (28) | Boots (7) | Similar Ring
Here’s another look at one of my most-worn outfit combos as of late. This Free People sweater + my trusty Levi jeans + my Leona Boots are all winning pieces on their own but together they are *chef’s kiss.*
Outfit 9: Mango Wrap Sweater + Gap Barrel Jeans + Leona Doc Martens
Sweater (M) | Jeans (M) | Boots (7)
This winter I’m freely embracing my love of all the oversized comfy clothing and this wrap sweater and these Gap jeans are about as comfy as they get! Unfortunately, this wash is sold out at Gap but these are seriously some of the most comfy jeans I’ve ever owned.
Outfit 10: Mango Cropped Cardigan + Daze Jeans + Leona Dr Martens
Cardigan (M) | Jeans (28) | Docs (7)
Mango for the win, again! Can you tell I am a big fan of their brand right now? I think the quality is great for the price point and I love how many cool pieces they have lately. Also, I can’t say enough about how much I’m loving Daze denim right now. It’s super chic and affordable. (I’m working on a Daze denim try-on coming soon.) I love these jeans, but I exchanged the above size 28, because they definitely run large and the 27’s fit much better although I haven’t snapped a pic yet.
Outfit 11: Free People Oversized Sweater + Free People Cargo Pants + Leona Docs
Sweater (M) | Pants (M) | Docs (7)
This outfit is brought to you by Free People 😉 Jk. It’s not sponsored but the whole outfit is Free People of course, just in case you thought I was over my Heart You sweater, I’m not. Also, these We the Free Can’t Compare Slouch Pants are some of the most comfortable pants in my closet but almost sold out everywhere.
Outfit 12: Mango Cropped Cardigan + Mango Wrap Denim Skirt + Leona Dr Martens
Cardigan (M) | Wrap Skirt (S) | Docs (7)
This might be one of those outfits that looked better in my head but hey, can’t say I didn’t try! I’ve been really wanting a denim wrap skirt lately and so when I saw this Mango Sarong option, I jumped on it. It’s a bit thin material for Michigan winter but still cute. I am also eyeing this denim wrap skirt from Ann Taylor, and might try it out.
That’s all for now, friends! I hope you enjoyed reading this post as much as I enjoyed writing it. Thanks for reading!
xo, Jess ( My Instagram | More of my Posts )
