DO THIS DON'T: Dress Like A Grandpa For Fall

Grandpa style is all about comfort and wrinkles and bagginess and the faint, musty smell of approaching death.
Publish date:
October 15, 2014
shoppables, style, grandparents, target, loafers, oxfords

Normcore has been a thing for a while now, but I was never into the idea of dressing like a dad. However, I can't wait until my latest style rut catches on: dressing like a grandpa. It's going to be all the rage, so I suggest you get started now so that you can say you were cool before everyone else.

Luckily, autumn is the perfect time to stock up on everything that you need to pull off grandpa style: thick glasses, chunky cardigans, comfy trousers, wrinkled button downs, and old man shoes like oxfords and loafers. I accumulated all of these items so gradually that I didn't even realize it was happening until I showed up for work at the library one day to find an elderly man wearing the same outfit as me.

There's a lot to be said for this style, though, as long as you don't treat it like a Halloween costume complete with dentures and a cane. You'll be comfy, you'll be warm, you don't have to worry about flashing any inappropriate skin at the office, and it's surprisingly effective at stopping random men from hitting on you.

And if you’re thinking, “Well, what’s the difference between this and the regular menswear trend?” I will tell you: There’s a big difference. Menswear is all about perfect tailoring and sleek proportions and shininess and the sexiness of wearing a crisp men’s shirt with the faint smell of cologne. Grandpa style is more about comfort and wrinkles and bagginess and the faint, musty smell of approaching death. Um, am I selling it for you yet?

Let’s hope! Below I put together two of my favorite cranky old man outfits that I've been wearing to work a lot.

This is the basic look: a button down, an oversized cardigan, trousers, and loafers. Sometimes I add lipstick in a half-hearted attempt to remind people that I'm a lady, dammit.

Both pairs of pants are the Pixie Pants from Old Navy. For button downs, I recommend that you get a silk one from Everlane, a chambray one from Old Navy (that’s where mine is from), and several basic cotton ones (the Target brand Merona has lots of these that will get the job done just fine). The men’s section, whether it’s at J. Crew, H&M, or the thrift store, is a great place to find baggy, slightly itchy sweaters. For all of this, stick to neutrals or muted colors like mustard, burgundy, and navy.

As for shoes, if you have larger-than-average feet then the men’s section at the thrift store is always the perfect place to find worn cast-offs from all the grandfathers in your community. Thriftiness is an important element of this style, remember. Both of my pairs of loafers were found at second-hand stores, and they have that special old man feet scent. Authentic!

In case you’re not into that secondhand shoe smell (or you have dainty lady feet, unlike me), here’s some other options.


Oxfords are also acceptable footwear for this style. I see a lot of these at thrift stores too although I got my pair from Target years ago. I wear them often but they're still holding up well, and I like how they're a slightly more feminine style. I also love heeled oxfords; I like how they make me feel like an old-fashioned schoolmarm (although that’s a different style post altogether).

That said, I’m currently on the hunt for the perfect pair of menswear-style oxfords. Here I’ve rounded up a combination of both masculine and feminine oxfords.

Back when I was a bright-eyed, bushy-tailed college graduate with hopes and dreams, I would shave my legs and wear cute dresses and painful pumps to work. Now I no longer care. The AC at my work was cranked up so high that I dressed like a hibernating grandpa all summer, and now I'm going to continue to do so all the way through fall, winter, and eventually the spring. I just want to be warm and cozy, and eventually go home to watch "Downton Abbey" with a plate of cheese and crackers. Oh my god, I really have turned into my grandpa.

When that realization hits, it might be time to spice things up a bit. Switch out the loafers and oxfords for, um, loafer heels and oxford heels. Put the plaid pants aside for a day and try a cute plaid dress instead. And there's no harm in wearing a fitted blazer from time to time instead of a bulky sweater.

This outfit allows me to indulge in my taste for somewhat preppy and vintage styles without looking like I literally raided my grandpa's closet. It's cute and totally office-appropriate, although this particular dress is a bit short -- good thing it’s now tights season. Ahem: I mean, long underwear season.

Of course this is nowhere near as comfy as my baggy plaid trousers and loafer flats, so I only break this outfit out every once in a while when I need to remind the world that I have legs. Then I quickly go back to working on my night cheese while wearing a giant sweater and silently agreeing with everything Carson grumbles on Downton.

So what do you guys think of this aesthetic? I’d be interested in hearing what dressing like your grandpa means for you -- I realize that for some people that might mean boat shoes and polo shirts, so I can understand wanting to sit this one out if that’s the case.

Photos by Joshua Kirby