19 'Sex And The City' Men's Outfits That Are So Dated, It's Honestly Painful

The women of Sex and the City are known for their impeccable fashion sense – and, occasionally, their totally outdated '90s styles that are so ridiculous that you can't help but love them. While it's somewhat difficult to notice anyone else through that haze of pink tutus, sky-high Manolo Blahniks and fabulous power suits, a look back at the men of SATC shows that they, too, had their own fashion ups and downs – you just might have been too distracted by Samantha’s newest handbag to notice them.

Hey, I know that it was the '90s, and everyone made questionable style choices, but there are some SATC male fashion blunders that are too priceless to miss. From Mr. Big's awkward beginnings to the in-your-face prints and terrible hats worn by Carrie and the gang's rotation of flings, any self-respecting fan will surely remember these undeniably outdated outfits.

Let’s take a moment to reminisce about our favorite loves lost, our most hated exes, and their hilariously dated '90s wardrobes with these photos from the SATC archives. But we have to warn you: While these cringeworthy moments are sure to make you laugh, their datedness might also make you a little sad when you realize just how long it’s been since SATC first aired. Reunion, anyone?

1. Everything Skipper Ever Wore

Looking back at Skipper's wardrobe over the course of his character's seven episodes is like looking at a time capsule of terrible '90s men's fashion.

2. Smith's Cut-Off Graphic Tees

This terrible T-shirt is actually kind of breaking my heart.

3. Mr. Big's First Suit

You can't go wrong with a classic suit — unless it's this terrible '90s suit that Mr. Big wears in the pilot episode.

4. Berger's '90s Bro Style

OK, he was hot. But tortured writer Berger broke up with Carrie via a three-line Post-It note. And he dressed more like he was in a Kevin Smith movie than running with a crowd of Manhattan fashionistas.

5. Buster's Glasses

Who could forget the creepy shoe salesman who hooked Charlotte up with pricey Manolos for a chance to get closer to her feet? If that wasn't enough to make you remember Buster, those tiny '90s glasses definitely were. I mean, can he even see out of those things?

6. Smith's Biker Cut-Offs

It's one of the most romantic scenes in the show's history, but when you rewatch the episode in which Smith tells Samantha his true feelings for her, all you can think about is that awful cut-off shirt. At least he's got those arms ...

7. Greg's Hawaiian Shirts

Greg was supposed to be Charlotte's hip 20-something fling, but those awful Hawaiian shirts make him look way older than that — and way less hip.

8. Aidan's Backwards Baseball Cap

Many a SATC fan would argue that Carrie should have ended up with Aidan instead of Big, but I'm not even sure that his dedicated pack of loyal supporters can explain this unfortunate backwards baseball cap situation.

9. Richard's Silk Robes

Richard's silk robes are the definition of tacky, which I feel comfortable saying, because he cheated on Samantha and can never be forgiven.

10. This Shirt …

11. … And This Shirt …

12. … And Yep, Also This Shirt.

Aidan was pretty amazing — not to mention a total babe — but the guy had some truly terrible shirts.

13. Ray's Pork Pie Hat

He is wearing a Pork. Pie. Hat. That should have sent Carrie running from the minute she met him.

14. Whatever Smith Is Wearing Here

Mark Mainz/Getty Images Entertainment/Getty Images

It's kind of hard to believe that someone as good-looking as Smith Jerrod could ever wear the wrong thing. But man, does he prove us wrong time and time again.

15. Trey's Preppy Pastels

Trey wore more pastels in three seasons than I've worn in my entire life.

16. Stanford's Fierce and Fabulous Patterns

Stanford Blatch has some of the most recognizable ensembles on a show that is very well-known for its fashion sense, but I'm not really sure if this one stood the test of time.

17. Steve's Oversized Everything

Sure, Steve was a small guy, but why were all of his shirts so damn big? I find it hard to believe that he was constantly around that many fashion-savvy women (and men, for that matter), and not one of them ever gave him the name of a good tailor.

18. / 19. The Russian's Many Scarves

As if he couldn't get any more pretentious, he wore an ascot. I know he was an artist, but come on.

Images: HBO; Getty Images