My most popular post (so far) is How to Wear Dr. Martens at Any Age. I continue to get strong traffic to that post. I am happy to see so many women embracing their unique style and abandoning the “rules” for women over 40.
When I first started blogging, I planned to avoid titles that referenced age. I firmly believe at middle age; we have earned the right to write our own rules. So a fashion post written by a millennial is as relevant to me as a 30-somethings. But I continue to be dismayed to see posts written with expectations of women of a certain age.
The only thing women should be giving up at midlife is doubting themselves, negative thinking, fear of failure, and people-pleasing.
Dr. Martens have always been about breaking the rules and shirking authority. So it gives this rebel heart all the feels to see women everywhere embracing their inner badass and wearing what they want. My Dr. Martens Leona Boots are still in regular rotation. Most often I wear my Dr. Martens with skinny jeans. It’s a tried and true outfit. Here are some additional ways to wear them with all your favorite jeans.
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Outfit #1: Dr. Martens + Corduroy Flares + Sweater
Pair your favorite Docs with the Free People Pull-On Corduroy Flares. Mine appears to be sold out currently. Christmas has undoubtedly depleted lots of inventory, but at only $78, these are a best seller and will surely be back.
Add an interesting sweater for a pulled-together look. Mine is by Madewell 2020, but this one is similar. Here are two other fun options from Everlane or Something Navy.
This outfit would also work with your favorite oversized sweater or plaid shacket.
Style Tip: When the pants have a distinct 70s vibe, keep the rest of your outfit modern to avoid looking too costumey. So skip the fringe (coming back in 2022), floppy hat and vests.
Outfit #2: Dr. Martens + Sweater + Jeans
Add your favorite Dr. Martens to classic outfit combinations. I don’t know if it is a result of Covid but who has time for fussy clothing anymore? Keeping outfits straightforward is always a stylish option. You could find me wearing this outfit pretty much any day of the week. A classic pairing of jeans and a cashmere sweater are leveled up a notch by adding a pair of Dr. Martens.
You can wear Docs with all your favorite jeans: skinny, straight, cropped, or boot cut.
Sweaters: Cashmere Classic Crew & Cashmere Relaxed V-Neck Sweater
Style Tip: Look for juxtaposition in your outfits – hard & soft, feminine & but, or classic & trendy. The push/pull is what makes an outfit great.
Outfit #3: Dr. Martens + Sweatshirt + Sweatpants
If anything good came out of this whole Covid mess, it is the return of the matching set. As we all hunkered down, we wore only comfortable things. So as we started to open up, it was a shock to have to put on “real” clothes. The matching set came to rescue us. Now we can look fashionable, pulled together but remain comfortable. I mean. Why did we ever give them up?
Back in the early aughts, I lived in my Juicy Couture tracksuits. I had two littles and loved the practicality of the Juicy tracksuit. But, of course, now I am horrified by how low the rise was on those track pants. I was flashing my panties every time I went to pick up a child.
Matching Sets for the Win!
Now matching sets are available in sweatsuits, knitwear, cotton, and velour. There are so many fabulous sets; I am working on a post of my favorites. Below I am wearing a sweatsuit by Free People. The FP sweatsuit runs true to size. I am wearing a large for a baggier fit. I also have sets from Aviator Nation and Good American. But, by far, my favorite matching set is by Cotton Citizen.
Dr. Martens are the perfect shoes to wear with all your matching sets. It adds that edge to the soft, casual pieces. A sweatsuit is perfect for traveling by plane. Plane temperatures are unpredictable and often strangely cold. A sweatsuit will keep you cozy and warm.
Matching sets are perfect for layering. Add your favorite jacket for some additional warmth. Below I added the Free People Dolman Quilted Jacket. As with a lot of FP items, this jacket runs large. I am wearing a Medium.
Jacket: Free People Dolman Quilted
Style Tip: When buying a jacket consider whether you plan to layer thicker items underneath. I always size up to accommodate all types of tops.
Outfit #4: Dr. Martens + T-Shirt + Jeans
Add Dr. Martens to a simple outfit like a t-shirt and jeans for a relaxed, casual vibe. My t-shirt is by rag & bone. There is a small heart hiding behind my hair. For added warmth, add a blazer or a long sweater coat. Mine is from J.Crew and super cozy. Some version of this is my everyday uniform.
Yes, you can wear your damn skinny jeans. It amuses me that articles are now touting the return of the skinny jean when for most of us, they never went out. So, some Gen Z Tik Tokker classified them as Cheugy, we gave birth to Gen Z, and we have no time for such nonsense. As a member of Gen X, I knew if we just stayed quiet and did what we wanted, the practicality of the skinny jean would win out.
Style Tip: Style is personal, dress accordingly!
Outfit #5: Dr. Martens + Sweatshirt + Utility Jacket + Jeans
Dr. Martens look great with dresses. BTW, I covered dresses + Dr. Martens in my previous post. You can find it here. In this post, I’m focusing on current outfit ideas, and since we are still stuck in this Covid nightmare, it seems only fitting that the outfits be casual.
The combo of a hooded sweatshirt & utility jacket is one of my favorites. I am wearing the Military Shirt Jacket by Madewell. I first bought this jacket in black, and my daughter promptly stole it from me. So I bought myself another one. Once I realized how fabulous it was, I went back and purchased the olive green one.
My sweatshirt is from Everlane a few years back. The weight is perfect for layering or warmth in the summer. It is cropped but long enough to feel fully covered. I hope they make this sweatshirt again. My jeans are Citizen of Humanity Corey Slouch Slim.
Outfit #6: Dr. Martens + Oversized Sweater + Leggings
Keeping it real, I wear leggings a lot because I am at home most days. Even in the good old days before Covid, leggings were a staple in my casual style. Dr. Martens work perfectly with leggings. Dr. Martens upgrade the leggings from athleisure to pants. Add an oversized sweater and you have a casual, modern outfit.
My Favorite Pairs of Dr. Martens
- Leona Boots (I’m wearing in this post)
- Jadon Boot – Same as the Leona but with a zipper
- Bex Smooth Leather Chelsea Boot – Classic slip-on Chelsea
- 1460 Boot – The Original
Dr. Martens & My Last F’s
Dr. Martens just seems right for the times. I don’t know about you, but over the last two years, I gave my last f*cks. Actually, I don’t care what you think of me. I am going to do what is right for my family and me. It was the exact vibe I was going for when I was 16 and wearing Docs, but it was more an illusion during my teenage years.
Fifty is freeing that way. We finally rid ourselves of society’s expectations and emerge solid in our womanhood. Maturity is one reason I reject all of the “rules” others want to place on how we should dress. It is the reason Dr. Martens are made for women like us. So wear them if you want. Wear whatever you want.
I would love it if you followed me on Instagram for my everyday outfits or on Pinterest for my fashion inspiration. StyleDahlia is a fashion and lifestyle website with a modern take on midlife. We hope to inspire you to step out of your comfort zone, try new things, and live your life in full bloom.
