Do grandpas have drip? (and we’re not talking about an IV). Macklemore might have been on to something when he famously rapped about stealing his grandpa’s style in 2013.
Oversized, semi-ugly sweaters that look like they came straight from the 80’s (and by that we mean both the era and the age range) can actually be made to look really cute when styled the right way. In the cooler/transitional months, they’re a great layering piece and they should be extremely easy to find at your local thrift (likely in the men’s section).
Below are five looks to help inspire you to thrift a grandpa sweater:
With a Simple White Tank
Everyone has a simple white tank, and there’s a good chance you have a pair of denim cutoffs too. If so, this is one of the easiest ways to style a grandpa sweater. Uggs, Boston clogs, sneakers or loafers would all look great with a pair of high socks to complete the look
With Athleisure
Put the “leisure” in athleisure by pairing the sweater with a pair of bike shorts or leggings. It’s easy to throw on and adds some character to an otherwise simple athletic look
With Shorts and Docs
In general, the key to making a grandpa sweater work is to pair it with that is decidedly NOT grandpa-esque ( you don’t actually look like you’re well past retirement). Here the sweater is perfectly paired with a pair of tiny shorts and sheer tights, which is a great way to style this type of sweater.
With Knee High Boots
If you didn’t think you could wear a grandpa sweater going out think again. Pair your sweater with knee high boots, add some chunky jewelry and a shoulder bag and this is a perfect look for grabbing drinks with friends. You may feel like a grandma sometimes, but at least you won’t look like one.
With a Mini Skirt
I like to call this look preppy grandpa. Like if your grandpa’s last name was “Van Der Bilt” and he insisted you go to Yale instead of Columbia. (So basically if you’re Nate Archibald from Gossip Girl). Throw on a collared button down or turtleneck under the sweater and pair it with a tennis skirt and fully lean into your Constance Billard alter-ego.



