Fashion Challenges: What to Wear With White Doc Martens (Or Any Other Nostalgic-Trendy Shoe) When Your Alternawaif Days Are Behind You

I wasn’t planning on getting anything, really. I was just minding my business there in my local resale shop, walking up and down the aisles. I was waiting for the staff to rummage through the bag I had brought after doing my New Year closet cleaning. It wasn’t a big bag, so I knew I wasn’t going to get much for it — I thought maybe I would treat myself with the proceeds to a nice leisurely lunch on a work- and child-free afternoon. Whoo hoo, #momlife!

But then I saw them perched on a shelf: a pair of Doc Martens…white Doc Martens, too! Finding a pair of Docs in a resale shop is a bit of a dream for me — I still have vivid memories of being a teen in the 90s and making a pilgrimage to The Alley in Chicago in those pre-Internet days to buy those boots. I had a pair of black ones, but always longed for other colors but couldn’t afford them at the time. (Hey, I was 15! The best job I could get was a cashier at a Natural Wonders store at the mall!) Since then, Doc Martens have always been a symbol of ultimate alternative cool in my mind — I’ve written screenplays where silver Doc Martens play a pivotal role in the action, in fact!

Of course, I’ve grown and changed as a fashion person and gone onto covet other kinds of shoes since then. (Crazy Alexander McQueen gladiator heels, Frye engineer boots and more!) Now Doc Martens became this beloved symbol of a bygone era for me. But then I noticed the undergrads I taught during grad school beginning to wear them again. They have slowly crept back into fashion consciousness, but I vaguely have that rule in my head that one shouldn’t indulge in a nostalgic trend if you were around for it the first time.

All of this was flying in my head when I saw those white Doc Martens a few weeks ago. Part of me thought, “Oh, you’re not a teenager anymore.” Of course, me being me (and accessing my inner punk spirit), I thought: SCREW THAT! And so I ended up getting them for about $6, because how could I resist? My 15-year-old self would’ve been so disappointed in my present self if I hadn’t: $6 DOC MARTENS, GUYS!

When I got home, though, I wasn’t exactly sure how to wear them. Back then I wore Docs with everything: tights under denim shorts, babydoll dresses, long black dresses. (Yes, I was very grunge Goth…it was the 90s!) There are still hints of that aesthetic in my wardrobe now — Goth never dies, people — but I’d like to think that my taste is a bit more sophisticated. It’s certainly much more eclectic, and I just couldn’t see my adorably clunky white boots mixing well with my sophisticated silky Joie blouses, for instance. Or could they? I realized that my footwear choices have gotten a little more refined (and perhaps more conservative) over the years. Was I a grown-up when it came to shoes? Were these Docs too young for me? Was it ridiculous to have them. I was having a real moment of “Was this a wise choice?”

And then I stopped myself. Who cares! They’re fun! I’m living my 15-year-old dream! I’m going to figure out a way to make it work. And so here are my attempts. Did I succeed or not? I don’t know, but all I know is that they are just as fun to wear as I imagined all those years ago. I might not keep them forever, but they give me joy for now — and that’s just fine, because sometimes fashion is for now as much as it is for investment. We all need a smidgen of fun!

Athleisure Meets Grunge

Part of the tricky nature of white Docs, of course, is their color — if you look at my shoe collection, you’ll see that it’s primarily black with a few pairs of tan here and there. (I do have a pair of Loeffler Randall rose gold flats, but in my head that’s like tan.) Black shoes are simple no-brainers, but they’re also the least risky and I haven’t had a lot of practice with shoes of other colors.

But I do think white looks great as an accent, and right now, a lot of athleisure looks do white-as-an-accent-shoe well — witness the resurgence of Stan Smith-type of white sneakers. So that’s where I started. I kept it simple, with just leggings and a sweatshirt — but it looked a little too plain to my eye. (Plus, I need a haircut sooooo bad. #momlife!) That’s the other weird thing about Docs — they are a humble shoe, but also very distinctive with the air soles and the stitching. It needed, on me, another counterpoint, so I threw on a beanie, which made it kind of grunge. Anyway, wearing it this way — as part of my all-around embrace of mama-friendly athleisure with a soupcon of grunge — felt nice, like a merging of past and present selves in one outfit.

Skirts Rule

My next experiment went with an old template: the mini-skirt with a heavy clunky boot. There’s something really classically cool about that proportion: a nice heavy boot toughens up a gamine item of clothing. Here I paired it with the Fabletics neoprene skirt that figured so prominently in my winter fashion capsule challenge. I was at a bit of a loss when it came to the top, though — so I went with a classic Breton shirt because you can’t really go wrong with one.

Honestly, I didn’t quite feel at home in this outfit — maybe it was the white color of the boots, but I felt a little like a figure skater with the short skirt! Which is not a bad thing, of course, but not the typical feeling I like to go for in terms of my outfits. Still, this look might work on someone else in a different life situation or with a different fashion temperament. It’s cute and kind of a French mod-hybird, but it’s not quite right for me these days. I’m not an ingenue anymore, and I’m not trying to dress like one anymore.

The Hiking Boot Substitute

I was still feeling a little bedeviled by the white Docs when I realized I could try to use them as quasi-hiking boots. (Hiking boots of an orthopedic-punk edge, perhaps? LOL…) So I went for a Seattle-grunge-outdoorsy hybrid, with a vest layered over a sweater (I was feeling eccentric), leggings and…a beanie, of course. (I don’t know why, but wearing a beanie with these shoes seem to make them better!) I still had a hard time dealing with the whiteness of the shoe, but I can’t tell if that’s due to my comfort level with the shoe itself or the color.

The Final Analysis

In complete honesty, I never quite took lost my self-consciousness with these. I love these Docs as an object, but I am not sure I’m entirely a white shoe type of human. For better or for worse, I don’t think I’m inclined towards colored shoes — leopard print flats are, like, huge for me! I can imagine myself still wearing black or even cherry-red Docs, like I did in my young wildling days — once a Doc person, always a Doc person.

Still the few times I wore them, I did get more and more comfortable with them, so maybe it’s really just desensitization? Maybe I’ll begin to lose that ‘weird figure skater’ feeling. So who knows — maybe this is a good way to stretch my fashion boundaries in a natural direction I’d expand in! And my 15-year-old self would be so happy. As a grown lady and a mama, sometimes I lose sight of her, but maybe she’s someone that needs to come back to the fore, if only for joy’s sake.

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