Our love for The Vampire Diaries flashbacks is pretty intense, and one of the best parts about going back in time is seeing our favorite characters all dolled up in the fashions of the day. We’ve seen Damon (Ian Somerhalder) and Stefan (Paul Wesley) in many eras at this point, which has been fun, but we couldn’t help but notice something suspicious. Namely, that they always look good.

That (obviously) isn’t a bad thing. But is it realistic? These two have been vampires since 1864, and since then they’ve apparently been on trend in every era, while avoiding any and all regrettable fads.

Sure, they’re fashionable guys, and their love of the color black is hard to screw up, but we have a hard time believing they never made one sartorial misstep. Seriously, we didn’t even get to see Damon in ridiculous ‘70s clothes because he was a punk! Below are a few fashion fails we wish had happened, just for the fun of seeing one Salvatore or another fall victim to a fashion faux pas.

1. Zoot Suits

1940s rebels wore these ridic suits: High-waisted, wide-legged pants that tapered to the ankle, with a long coat that had wide lapels and wide padded shoulders. Bold, checkered fabric an added bonus.

2. Bellbottoms

Being a flower child is pretty antithetical to the vampire lifestyle, but the whole “free love” thing seems right up their alley. We would love to see a Salvatore in some massively flared pants, with maybe a fringed leather vest on top? Shirt optional. (JK! A shirt is not an option.) 

3. Leisure Suits

In the time of Barry Gibb and Saturday Night Fever, is it so crazy to believe that Damon or Stefan would wear a slim, white suit in a synthetic fabric while cruising the club scene? We think not.  

Credit: Wetpaint Entertainment Staff

4. Hammer Pants

Like it or not, these loose, drop-crotch pants made the rounds in the ‘80s. We’re not sure how much these vamps were into early hip-hop, but their super-strength definitely would have been kick-ass breakdancers, and parachute pants would have come in very handy.

 

5. Plus Fours

These short-pants for grown-ups, popularized by Prince Edward in the 1930s, made everyone look like they were going golfing at any moment. Add some argyle socks and we’re sold.

 

6. Denim on Denim

If a light-colored denim shirt tucked tightly into only slightly-darker jeans was good enough for George Clooney in the ‘90s, then it’s good enough for a Salvatore.

 

7. Grunge

The grunge era would have played nicely into Stefan’s whole “brooding” thing, so we think some trashed jeans paired with thermal and/or plaid shirts would be a good perfect on him.

 

8. Trucker Hats

Damon could totally have been partying it up Ashton Kutcher-style in the days of Von Dutch.


 Hairstyle Bonus: Frosted tips. If it was good enough for 80% of boy band members, it was easily good enough for an immortal badass, right? Anyone?