90s Throwback: Birkenstocks & Dr. Martens (Docs) — Comfort, Style & Break-In Tips

Originally published on December 30, 2017, and updated in November 2025 with a new video, refreshed insights, and never-before-seen photos.

The '90s: 'Stocks & Docs

Cartoon-style illustration of Gina Mama on Pier 39 in San Francisco, rocking jeans over classic black Dr. Martens with yellow stitching and a denim jacket — a nostalgic nod to her 1990s fashion roots.

If you grew up in the grunge era, you know: it was Birkenstocks or Dr. Martens—often both.  This is my ’90s style diary from Berkeley to Santa Barbara: Arizonas for sunny days, 1460s and Pascals for rainy ones; flannels, babydoll dresses, and mixtapes of The Cure, Pearl Jam, and Nirvana.  I’m sharing how I fell hard for Docs at 15 (after drooling over them on 90210), why Birks became my everyday comfort, and how both pairs carried me through dorm life, concerts, Tahoe trips, and everything in between.  You’ll find break-in advice, sizing notes, and authentic vintage photos—plus links to deeper guides like my How to Break In Dr. Martens and Beginner’s Guide to Birkenstocks, along with my Spotting Fake Birkenstocks checklist to help you shop smart today.

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90s Birkenstocks & Dr. Martens Video — How Comfort, Craftsmanship, and Style Evolved Over Time

🎥 Watch: 90s Throwback: Birkenstocks & Dr. Martens (Docs) — Comfort, Style & Break-In Tips

Before diving into my full story, take a quick trip down memory lane with this YouTube Short!  It features real photos from my 1990s Birkenstocks and Dr. Martens journey — from flannel-filled grunge days to my 2025 Cherry Red Docs still going strong.

Watch the video below, then scroll on for my full nostalgic walk through comfort, craftsmanship, and style evolution.  Don't forget to like and subscribe on my YouTube channel.

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Falling for Combat Boots and Birkenstocks — My ’90s Shoe Story

Just as Birkenstocks were the cornerstone of my 1990s and early 2000s wardrobe, Dr. Martens were right there beside them.  Docs might be the only other shoes—besides Birkenstocks—to which I’ve had such a deep (and possibly unhealthy) attachment.  I bought my first pair of black leather Dr. Martens at age 15, exactly one year before I slipped into my first pair of Birkenstocks.


I remember drooling over Doc Martens for months before my mom finally caved.  She thought they were “too clunky, too unfeminine” and didn’t understand my obsession.  Ironically, as I mentioned in my first blog post, Birkenstocks and Me, the only reason she ever bought me a pair of Birkenstocks was to convince me to wear something—anything—other than black combat boots.


Back then, combat boots defined the 1990s.  They were fashion staples for the Goth, Punk, and Grunge scenes—symbols of rebellion and authenticity.  If Robert Smith from The Cure wore Doc Martens, you needed a pair too.  Fans of The Cure, Nirvana, and Pearl Jam all wore Docs with pride, pairing them with babydoll dresses, flannels, ripped jeans, or whatever felt like you.  For me, those black 1460s weren’t just boots—they were freedom, identity, and the start of a lifelong love affair with shoes that tell a story.

My 1993 Dorm Room at UCSB — A Cure Fan’s Wall of Memories

A snapshot of my college dorm desk in 1993—complete with The Cure posters, Golden Gate Bridge prints, mix CDs, San Francisco Giants memorabilia, and the creative chaos that fueled my ’90s Birkenstock-and-Doc-Marten days. The Cure is pictured three times. Can you find them?

The Day I Finally Got My First Pair of Dr. Martens

I finally convinced my mom to buy me a pair of Dr. Martens after she saw Kelly and Donna on Beverly Hills 90210 rocking their Docs with pretty floral babydoll dresses.  Suddenly, combat boots weren’t just for punk rockers or goth kids—they were officially cool-girl chic.  Kelly and Donna made Dr. Martens look feminine, fun, and fashion-forward, and that was all the proof I needed.


To seal the deal, I promised my mom I’d style my Docs in the most “girly” way possible—maybe even with a flowery dress or lace socks—just to get her on board.  I also agreed to take on extra household chores in exchange for a shopping trip to Bancroft Clothing in Berkeley, the iconic Bay Area store where every cool kid shopped in the ’90s.  That’s where I bought my very first pair of black leather Doc Martens—a defining fashion moment that marked the start of my lifelong love affair with comfort-meets-rebellion footwear.

90210 Fashion Icons: Kelly and Donna in Doc Martens

Kelly and Donna from Beverly Hills 90210 made Doc Martens mainstream in the ’90s—pairing chunky combat boots with floral babydoll dresses. Bonus: the extra in the background is rocking Birkenstocks, proving that ’90s style was all about comfort and individuality.

From Grunge to Graduation — Living in My Dr. Martens and Birkenstocks

Once I finally got my beloved Dr. Martens, there was no chance I was pairing them with dresses.  I hated wearing dresses then and still do in 2025.  Besides, I was too busy styling my Docs with baggy jeans, oversized flannel shirts, and homemade cut-off shorts—pure ’90s grunge fashion.  I never went full Goth like some of my fellow The Cure fans, but I definitely embraced that laid-back, rebellious look that defined the decade.


Just like I style my Birkenstocks today, back then I made my Docs my own.  I wore those black leather combat boots everywhere—for years. When I wasn’t wearing my Birkenstocks in high school, I was lacing up my Docs.  I wore them on the day I left home for college, all through my Santa Barbara days—classes, parties in IV, late-night study sessions at the library, and even beach walks.  My Docs survived everything, including the 1995 Santa Barbara floods, keeping my feet dry when no other shoes could.  I even had them on in 1996 when I shook President Clinton’s hand at a rally—proof that my favorite boots were with me through every major moment of my ’90s life.

​1990s Dorm Room Shoe Stack — Birkenstocks Meet Dr. Martens

My makeshift dorm room shoe rack in the mid-1990s, complete with a Birkenstock box tucked beside my Dr. Martens box. Proof that even in college, my two favorite footwear brands—Birkenstocks and Docs—shared the same shelf space.

From Tahoe to San Francisco to Colorado — My Dr. Martens Went Everywhere

My Dr. Martens were my constant companions throughout the 1990s.  I wore them with thick wool socks every winter break in Lake Tahoe—my go-to “snow boots” thanks to their sturdy leather, waterproof finish, and unbeatable traction.  Those boots carried me from one adventure to the next: on a cross-country road trip from Colorado to California, through countless rainy Bay Area days, and even into my first big-city experience interning at Live 105 in San Francisco.


By 1998, I was still proudly rocking my Docs when I started dating my now-husband—he hated them, but I didn’t care.  Comfort, confidence, and nostalgia beat fashion opinions any day.  I wore my Docs to grad school orientation, through internships, and even dressed them up for professional events. Eventually, when I landed my first “real” job, I retired my well-loved Dr. Martens to the back of my closet—right next to my Birkenstocks, where every chapter of my footwear story seems to begin and end.

1992 San Francisco Pier 39 Style — Gina Mama in Classic Dr. Martens

A true 1990s moment: Gina Mama rocking her black Dr. Martens boots with jeans and a denim jacket on Pier 39 in San Francisco. These were the same beloved Docs that defined her grunge-inspired, comfort-meets-rebellion style throughout high school and college and beyond.

The Docs I Couldn’t Let Go Of — A Decade in the Closet

I could never bring myself to donate my well-loved Dr. Martens combat boots.  How could I?  Those boots carried me through my teenage years, cross-country trips, college memories, and countless Bay Area adventures.  They were more than just shoes—they were part of my story.  No matter how many times I moved, those Docs came with me, tucked safely in the back of my closet like a time capsule of the 1990s.


My Birkenstocks actually wore out long before my Dr. Martens ever did.  Back then, I had no idea Birkenstocks could be recrafted or resoled, or else I would have restored every pair.  Meanwhile, my Docs sat untouched for over a decade, still housed in their original yellow box—complete with the clear plastic bag and extra yellow laces.  Every so often, I’d pull them out, dust them off, and smile at the creases and scuffs that told the story of who I was back then.

Saying Goodbye to My Original Dr. Martens — A Bittersweet Farewell

One chilly winter day in 2015, I decided it was time to add some edge back into my minimalist wardrobe.  I pulled my original Dr. Martens from the closet, smiling as I slipped my foot into those perfectly broken-in leather boots.  But my smile quickly faded—my beloved Docs no longer fit.

After two kids, my feet had changed, and my once-perfect size 7s felt like Cinderella’s glass slippers on the wrong feet. I tried thinner socks, no socks, even wiggling and forcing my foot into the boot, but there was no chance—my iconic 1990s combat boots were officially too small.


I was crushed.  These were the boots that had seen me through high school, college, road trips, and first jobs.  They were broken in, molded to my feet, and full of memories.  Still, I couldn’t let them go.  Back in the closet they went—again—this time for another year.


When I finally tackled a full closet declutter, I knew it was time.  I placed my Dr. Martens, original yellow box and all, into the donation bag.  A cobbler couldn’t stretch them without damaging the leather, and keeping them felt selfish when someone else could love them like I once did.  Donating them was surprisingly emotional—it felt like saying goodbye to a piece of myself.  The only comfort came from imagining someone new stepping into them and making their own memories.


After parting with my Docs, I thought about buying a new pair, but the timing wasn’t right.  With toddlers to chase, I didn’t have the energy for another break-in period.  Besides, I was deep in my Birkenstock era—living in cork comfort and still carrying my ’90s shoe nostalgia in my heart.

The Christmas Eve Epiphany — Baking in Birks, Dreaming of Docs

It wasn’t until Christmas Eve 2017 that I realized I needed a new pair of Dr. Martens in my life.  In the middle of a chocolate chip cookie–baking marathon, covered in flour and wearing my trusty Birkenstocks, it hit me like a holiday light bulb moment—I needed to bring the Docs back.  Standing there in my kitchen, I thought about my old black combat boots and how they’d carried me through so many chapters of the ’90s and 2000s.  Those boots were tough, comfortable, and effortlessly cool, and I suddenly missed that feeling of sturdy leather and attitude underfoot.


That was the moment I decided it was time: my Birkenstocks could take a well-deserved break, and a new pair of Dr. Martens would soon be stepping back into my story.

Baking in Birks — The Christmas Eve That Sparked a Doc Martens Comeback

Christmas Eve 2017: in the middle of a chocolate chip cookie baking frenzy, I looked down at my favorite burgundy suede Birkenstocks and realized it was time to bring Dr. Martens back into my life. My “Baking in Birks” moment turned into the spark that reignited my love for combat boots.

Shopping for Docs (Again) — Baking Cookies, Breaking Rules, and Following Comfort

While the cookies were in the oven that Christmas Eve, I grabbed my laptop and headed straight to Zappos.  Their Dr. Martens selection was just as tempting as their lineup of Birkenstocks—classic styles, bold colors, and that signature mix of comfort and rebellion I’ve always loved.  As I eagerly added a pair of Docs to my cart, my husband walked in and said, “Aren’t those so 1990s? You don’t need these.”


Mind you, this is the same man who hated my combat boots when we started dating back in 1998.  Did I care then?  Nope.  Do I care now?  Absolutely not.  The minute he left the room, I added two more pairs to my cart!


It’s simple psychology which I’ve written about before in my post Gina Mama, You Should Try.  It's Brehm’s Reactance Theory (1966), a classic concept in psychology that explains a very human reaction: when someone feels that their freedom to choose or act is being restricted or threatened, they often respond by doing the exact opposite of what they’re told not to do.  I’ve always believed in wearing what makes me feel good—whether it’s Birkenstocks, Dr. Martens, or anything else that keeps me comfortable and confident.  Fashion should never be about approval; it should be about joy.

Matching Docs, Matching Socks — A Friendship Decades in the Making

After years of shared memories and fashion phases, one of my lifelong BFFs and I discovered we weren’t just both wearing Dr. Martens—we were unknowingly rocking the exact same patterned socks too. Proof that real friendship (and good taste in boots) never goes out of style.

Online Shoe Shopping, Wine, and the Return of My Dr. Martens Obsession

Why did I order three pairs of Dr. Martens?  Simple—because I’m a mom.  Going to a shoe store with kids is pure chaos: think banging your head against the wall while someone yells in your ear.  Online shopping is my sanity saver.  With speedy shipping and free returns, Zappos has become my go-to for both Birkenstocks and Docs.  I knew each Dr. Martens style would fit differently, so ordering three pairs let me compare them quietly, at home, in peace—and in socks that actually matched.

Just as I hit “purchase,” an old friend stopped by for some Christmas Eve cookies and wine.  The same friend who drove with me down to college in 1993—and she was wearing her own pair of Dr. Martens!  They looked practically new, though she’d owned them since 1999.  Between sips of Napa Valley wine and bites of fresh-baked cookies, we reminisced about our shared history with combat boots, music, and fashion.  Docs weren’t just shoes—they were memories stitched in leather.

My original boots were made in England, back when Dr. Martens production was still based there.  The new pairs from Zappos weren’t, but honestly, if the fit was right, I could overlook it.  And fit they did—each pair uniquely.  It reminded me of Birkenstock styles: once you’ve worn Arizonas, trying Gizehs feels familiar but distinct.  In the end, I kept the Pascals in Cherry Red Temperley—a softer, sleeker evolution of my first beloved black 1460s.  A new chapter in my lifelong love story with Docs had officially begun.

Dr. Martens Pascal Cherry Red Temperley — A New Chapter Begins

My fresh pair of Dr. Martens Pascal boots in Cherry Red Temperley leather — buttery soft, perfectly smooth, and ready to be broken in the Birkenstock way. These beauties mark the start of my 2017 Doc Martens comeback and a new era of comfort-meets-rebellion style.

Breaking In Dr. Martens vs. Birkenstocks — My No-Blister Game Plan

The boots fit—but wow were they stiff.  Just like a fresh pair of Birkenstocks, new Dr. Martens demand a real break-in.  I’ve done this before (30 years ago) and I can do it again.  I’m leaning on the same techniques I use for Birks—gradual wear time, smart socks, conditioning the leather, and patience—to create a no-blister break-in for my Docs.

I’ll document the whole process and compare how Dr. Martens break in versus Birkenstocks: AirWair footbeds molding underfoot vs. contoured cork, and leather uppers shaping to my toes over time.  The goal is that perfectly conformed combat boot feel—supportive, flexible, and insanely comfortable.

If you’ve broken in Dr. Martens, I’d love your tips—especially what worked differently from breaking in Birkenstocks.  Email me with your best Doc Martens break-in tricks so I can test them and report back.

Documenting the Dr. Martens Break-In Journey — The Birkenstock Way

I actually followed through on my plan to document the process of breaking in my new Dr. Martens and turned it into a full blog post. The result is How to Break-In Dr. Martens, the Birkenstock Way.

In this freshly updated 2025 version of my 2018 classic, I share my complete Birkenstock-inspired break-in method—how I condition stiff leather, layer socks, protect pressure points with moleskin, and gradually flex the boots until they fit like a dream.  The post now includes a printable step-by-step checklist and a brand-new YouTube video showing my real routine in action.

You can also watch my full YouTube video How to Break In Dr. Martens, the Birkenstock Way here:

Breaking in Docs is a journey, not a sprint. The secret is to let the leather mold naturally while keeping your feet happy in between wears (hello, Birkenstocks!).  If you take it slow and care for both your boots and your feet, you’ll end up with perfectly conformed Dr. Martens that feel as good as your favorite cork footbed sandals.

2025 Update: Still Standing Strong After 8 Years

Nearly eight years later, my beloved Dr. Martens are still going strong.  The leather has softened into that perfect, lived-in feel, with a rich patina that tells their story step by step.  The signature AirWair soles continue to deliver that springy, cushioned support that makes Docs so timelessly comfortable.


Eventually, the inside began to show a little wear — a clear sign of just how many miles I’ve walked in them.  When my heels and arches started to complain, I slipped in a pair of Cushion Shoe Insoles, and just like that, they felt brand new again. It’s proof that with a little love, conditioning, and maintenance, a great pair of Dr. Martens can truly last a lifetime.


And yes — I still have the same friend mentioned in this story.  She’s the reigning axe-throwing champion I wrote about in my blog A Birthday Getaway to Lake Tahoe: Lifelong Friends, Laughter & Birkenstocks: Bears, Birks, & BFFs.  Some things, like true friendship and a good pair of Docs, only get better with time.

My Cherry Red Dr. Martens — Still Going Strong Eight Years Later

These Cherry Red Temperley Dr. Martens have been part of my life since Christmas Eve 2017. After countless adventures, weather changes, and wardrobe evolutions, they’ve softened beautifully and molded perfectly to my feet. Eight years later, they’re still as comfortable, stylish, and full of attitude as the day I broke them in—the ultimate proof that well-loved boots only get better with time.

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More Comfort Classics You’ll Love

If you enjoyed this 90s throwback to Birkenstocks and Dr. Martens, keep exploring these comfort-driven, nostalgia-infused favorites from the I Love Birkenstocks blog:

How to Break In Dr. Martens, the Birkenstock Way
Break in your Docs without the blisters using my Birkenstock-inspired method — leather conditioning, sock layering, and patience. Includes a printable checklist and YouTube demo.

Birkenstocks: The Ultimate First-Time Buyer’s Checklist
Thinking about your first pair of Birks? Learn how to pick the right style, width, and footbed for all-day comfort and longevity.

How to Break In Your Birkenstocks
My tried-and-true step-by-step routine to soften straps and shape the cork footbed naturally — no pain, just perfect fit.

Birkenstock Boots — Cold Weather Comfort Meets Classic Cork Support
Explore how Birkenstock reinvented their legendary footbed for the cold-weather season. Compare warmth, traction, and support to your favorite Docs.

How to Fix Squeaky Leather Solovair Derby Boots
Tackle squeaks and stiffness in any leather boot, from Solovairs to Docs, with my quick DIY fix and conditioning routine.

Shearling-Lined Birkenstocks Part 2 — Cozy, Supportive, and Winter-Ready
Stay warm without sacrificing arch support — a full review of Birkenstock’s fuzzy favorites for the cooler months.

Love comfort, craftsmanship, and shoes that tell a story?

Explore more on ilovebirkenstocks.com and check out my Videos page for tutorials, reviews, and behind-the-scenes style moments.

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FAQs About Birkenstocks & Dr. Martens

Are Dr. Martens or Birkenstocks better for all-day comfort?

It really depends on your foot type, arch height, and how you plan to wear your shoes.  Birkenstocks are known for their contoured cork footbeds that mold to your arches for orthopedic-level support, while Dr. Martens rely on their AirWair cushioned soles to absorb impact and provide shock resistance.  For extra comfort, you can add a Birkenstock Blue Footbed or Comfort Insole to your Dr. Martens boots—a simple trick that combines cork support with sturdy leather.


If you prefer to stay within the Dr. Martens family, the brand offers its own insole options including the Cushion Shoe Insoles, Fresh Cork Insoles, and Leather Insoles, all designed to fit perfectly inside 1460s, Pascals, and other classic styles.  Both brands share one thing in common: the more you wear them, the more they mold to your feet and become even more comfortable over time.


How long does it take to break in Dr. Martens?

Typically 2–6 weeks, depending on the leather type. To speed it up, use socks, conditioner, and short wear sessions — just like my Birkenstock break-in method.  Read my blog How To Break In Dr. Martens (Doc Martens) the Birkenstock Way — Step-by-Step No-Blister Guide to get the free downloadable guide on just how to ease into your Docs without pain.


Can I wear Dr. Martens with socks like Birkenstocks?

Absolutely.  Wearing thick, high-quality socks during the break-in phase can make a huge difference—they help soften stiff leather, prevent blisters, and speed up the process of molding your Dr. Martens or Birkenstocks to your feet.  For classic comfort, Dr. Martens offers a range of styles like their Frill Organic Cotton Socks for a vintage 90s vibe,  Athletic Logo Cotton Blend Socks for everyday wear, and WarmWair Organic Cotton Socks for extra warmth in cooler weather.


If you’re more of a Birkenstock fan, the brand’s Cotton Tennis Socks and Cotton Slub Socks are perfect for pairing with Arizonas, Bostons, or clogs during the chillier months.  Personally, my favorite socks to wear with both Birks and Docs are Bombas—their cushioned soles, seamless toes, and breathable cotton blend make every step feel like walking on clouds. Whether you choose Dr. Martens, Birkenstock, or Bombas, a great pair of socks is key to achieving that perfect, broken-in comfort.


Were Birkenstocks and Dr. Martens popular in the 90s?
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Yes!  Birkenstocks and Dr. Martens were absolute icons of 1990s fashion—and they’re just as popular in 2025. From the halls of Beverly Hills 90210 to college campuses across the country, both brands perfectly captured that comfort-meets-style aesthetic that defined the decade.  I practically lived in my Birkenstocks and Docs during the grunge era—and honestly, I still do today.  Their timeless mix of comfort, durability, and effortless cool keeps them just as relevant for modern wardrobes as they were back in the ’90s.

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Adding a Floral Twist to My Classic Docs | Follow me on Instagram @ilovebirkenstocks for all the twists and turns of I Love Birkenstocks

By 2021, my Cherry Red Dr. Martens got a cheerful refresh with these floral laces. After years of wear, the leather developed a deep, rich patina that pairs perfectly with the pop of color. A little customization kept my beloved boots feeling fresh, fun, and completely me—proof that timeless style never fades, it just evolves.

Dr. Martens 1460 Rainbow Ray Suede Boots October 2021 Purchase | If you love footwear with personality, join my private Facebook group for exclusive style chats, fit tips, and fellow shoe enthusiasts who get it.

Meet my Dr. Martens 1460 Rainbow Ray Suede Lace-Up Boots — a bold mix of shimmer and texture that shift from blue to violet in the sunlight. These iridescent Docs are proof that comfort and statement style can coexist.

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