Although there are plenty of options to choose from, Scott Disick is one of my favorite people on Keeping Up With The Kardashians. Despite Khloé Kardashian's boldness, I'd argue that Disick has the most outspoken personality of the group. After all, he calls himself "Lord Disick" and refers to everyone else as peasants. Humbleness isn't his strong suit, but he's pretty hilarious. Sure, he hasn't had the easiest time in his personal life, but I'm one of those Disick and Kourtney Kardashian shippers that's always rooting for him to get his life in order and reunite with the mom of three.
As any loyal KUWTK fan knows, Disick has grown up a ton over the years. He used to be that party bro, who shoved money in a waiter's mouth and couldn't be brought in public without some drama. News about him partying occasionally makes its way into headlines nowadays, but for the most part, he seems to be working on improving his life. Plus, now he has several children — Mason, Penelope, and Reign — that appear to be a big part of his life.
Just as his personality has developed over the years, so has his personal style. Here's a round-up of some vintage Lord Disick photos that will make any fan cringe-slash-smile instantly.
1. Twinning With Jonathan
Is it just me or do these two look like fraternal twins? It's slightly scary how much these look alike. On top of that, I can't even handle their wardrobes.
2. That Hoodie
Did Disick buy that hoodie at American Eagle or Hollister? He appears to be dressed like every guy I went to middle school with — baseball cap and all.
3. Sports Fan
While I knew he's a fan of flying planes, I had no idea that Disick was so sporty, yet here he is rooting for the Giants.
4. Lounging By The Pool
Between the chain and the belt buckle, I cannot handle this. He looks like a wannabe rapper in this get-up. The guy on the left's face looks exactly like my face when I saw this photo.
5. Prom Pose
Were they attending the high school prom here? This is the kind of picture that Mason, P, and Reign will look back at one day and chuckle.
6. The Sunglasses
With that pose and those shades, I have no words.
7. Former Couples
For some extra nostalgia, here's the zoomed-out shot of the image above. So many couples that no longer exist. It's heart-wrenching, really.
8. Posing With Kim
It feels like the MySpace days and these two are trying to master the T. Swift heart-hand pose.
9. Christmas Spirit
Those stripes are so festive! Also, baby Mason wins this photo.
10. Baby Faces
This is an oldie but a goodie. They seriously look so, so young.
I love Disick's facial expression (a combination of pride and fear), just as much as I love Kourt's velour track suit.
It looks like Kim has mastered the art of smiling with her eyes, as Disick struggles to smize.
13. Polo Shirt
Without any facial here, Disick looks pretty young here.
14. Pink Pants
Gotta love the pink pants! Although it wouldn't have hurt to iron them. To be honest though, I'm not quite sure this whole outfit even matches.
15. This Book Cover
Am I the only one who didn't know that Disick used to be a cover model?
16. "Healing Horses, Healing Hearts"
These covers are too good, I just had to include both. Also, I need these YA books on my shelf, stat.
17. Grease Wannabe
Posing with his beer feels very college and that jacket feels very Danny Zuko from Grease.
18. Young Love
Disick is rocking a bathrobe and shorter-thank-usual haircut in this throwback.
LOL at Kourtney's facial expression and Disick's caption about their life Before Kids.
20. Basketball Star
I take back my earlier comment about him not being into sports. Obviously this photo proves otherwise.
21. Long Hair, Don't Care
The quality here isn't the best, but it's worth it to see that haircut.
22. Backwards Cap
From the bangs to the backwards cap, it's like a whole different time.
23. Meeting Kourt
How sweet! This is from the first night these two met. How young does Disick look?
24. No Pictures, Please
You know this shot is old when it's a picture of a picture from Kourtney's computer. Also, Disick is most definitely flipping off the camera.
25. 25th Birthday
This photo is from seven years ago. Time flies, huh?
26. Cool Guy
Doesn't Disick look like he's trying really hard not to care in this photo? Like a forced tough guy persona.
27. Men's Fitness
In 2011, he appeared on the cover of Men's Fitness. Although it's an old pic, his face somehow looks more aged than it does now.
28. Bend It Like Beckham
A long-haired Disick hangs court-side with David Beckham. Now that's a random pairing.
29. All Dressed Up
The former couple has never looked classier.
30. Beach Towels
I wonder if he purchased any of those Kardashian beach towels. Especially since he looks so thrilled to be posing alongside them.
31. Sweater Weather
I'm digging the cozy-looking sweater.
32. Baby Mason
Once again, Disick looks just like Cheban. This furthers my theory that they're secretly twins.
33. Hanging With Kim
Apparently anytime he hangs out with Kim, their posing game is on point.
34. Batman & Robin
These Halloween costumes sure are super.
35. Season 1
This screenshot from Season 1 of KUWTK looks like two entirely different people.
36. Slicked Back Hair
Honestly, this may be my favorite hairstyle yet. It looks super sleek and chic.
37. The Transformation
A fan compiled these photos of Disick over the course of the show and it's pretty crazy to see all the snapshots side by side. Adorable!
38. Elementary School
I'm not 100-percent sure this photo is real or where it came from, but it does appear to be Disick in the second grade.
39. The Good Old Days
Even though Kourt's grinning, he couldn't look more unamused to be in the photos.
40. Season's Greetings
A few years back, he joined in on the annual Kardashian Christmas card. Check out Mason's mini tuxedo!
Disick's summer ensemble is uhhh, interesting? I can't even figure out what the pattern on his shorts is supposed to be.
42. Chuck & Blair
This is one of the photos that sparked an entire comparison of Disick and Kourtney to Chuck and Blair from Gossip Girl .
43. Louis Vuitton Bags Galore
Does it look like he has a favorite designer brand for luggage or what?
44. Bike Ride With Mason
This father-son photo is pretty darn cute.
Of course Lord Disick would carry around a cane as a prop.
The caption on the photo says it all.
47. Kris Humphries
You know this picture is old when Kris Humphries is in it.
48. A Mystery
Is this real or is it photoshopped? I genuinely don't even know what to believe. Unfortunately he didn't respond to that fan's tweet asking for confirmation, so it looks like the mystery remains unsolved.
Either way, wow — all this nostalgia is unreal! I can only hope Disick digs even deeper into the archives and shares more gems for future #TBTs.