- [Interviewer] This was your first World Series win,
this was '96.
How special was that one for you?
- It's the first.
Who was your first girlfriend?
You remember, don't act like you,
you just don't want to answer it
'cause you got a microphone on
but you always remember your first.
[upbeat music]
What's up everyone?
I'm Derek Jeter
and today we're gonna take a look at my style history.
[upbeat music continues]
- [Interviewer] Who styled you right here?
[Derek laughing] - That's all me right there.
I mean that's,
there's nowhere to go but downhill after that.
Butterfly collar.
I do have to to get on my dad a little bit,
he used to cut my hair back in the day
so he's responsible for this.
I don't really know what you call it.
That should be a cover right there.
I like that picture though.
- [Interviewer] That was, I think Hannah's first post
when you first went on Instagram.
- Yeah, she didn't tell me about that either.
She just tried to have some fun with me.
I'll get her back.
[upbeat music continues]
- [Interviewer] Let's talk about the hairstyle here.
- Yeah, that's the Ralph Tresvant shag in the back.
I was very proud of the shag when I was in high school.
Used to wear my hat up high,
you know with the hair in the front.
There's nothing good about that, at all, man.
I wish I could go back.
[upbeat music continues]
Yankees are big on rules man.
I mean you can't have facial hair,
you can have a mustache,
you can wear one chain.
Hair's gotta be a certain length.
I see here, I don't know what year this is
but I see I lost the shag
but I still got a lot going on on top.
The boss was big on rules.
He would call down sometimes
and have guys shave between innings,
you know if their beards got a little bit long.
So he really paid attention.
So yeah, I mean I didn't grow facial hair 'til the pandemic,
pretty much from the time I was 18 till 45,
I mean I pretty much shaved every single day.
There it is, one chain that was big.
Big gold chain, you know.
[Derek chuckling]
You finally, when you play professionally
you make a little bit of money
but you really couldn't go overboard
'cause there was a rule to how many you could have.
So it was just one.
I switched it up from gold,
I think I went to platinum
and then at the end of my career was black diamonds.
My wife made, had it made for me.
[upbeat music continues]
- [Interviewer] June '97 you're at a fundraiser
with Cecil Fielder and Tino here,
it was also your birthday apparently.
- Either that or I wore the same outfit.
- [Interviewer] Who were some of your teammates
from the earlier years who you looked to for style guidance?
- I don't know if I wanna necessarily say
I looked to 'em for style guidance
but I can give you the teammates
that thought they had the best style.
Cecil Fielder is one.
Ruben Sierra is the other.
So go back, look at some old photos
of Ruben Sierra and Cecil Fielder.
These guys thought they were
the best dressed players of all time
and I think if you sat them down now
they would tell you the same thing.
[upbeat music continues]
I first met Michael in 1994 in the Arizona fall league.
So baseball has its fall league
where they'll send top prospects
after the season's over with
just so they can continue to develop.
And this was the year Michael had started playing baseball
and just got to second base
and he's like, you know what's up DJ?
I'm like, haha, I didn't know you'd know who I was.
And then ran into him a couple times out in Arizona
and he just sort of took me under his wing
and you know he was like a big brother to me now.
But you know Michael,
you look at these oversized suits man,
I mean everything was oversized
and I actually went to the same tailor,
I don't even know if he knows this,
I went to his tailor to have him make suits
'cause Michael was, you know, the sports fashion icon.
Everyone looked up to MJ
and yeah, they're a little big to say the least,
they're a little big.
You know, when he reached out to me
and wanted me to be a part of the brand, I,
yeah it was like no hesitation
and being the first baseball player and then wear his 11s,
turn 'em into cleats
and then develop my own shoe year after year,
it was a fun process man.
So I really enjoyed it.
It was an honor for me
because of what Michael represented on the court
but off the court really enjoyed that collaboration.
[upbeat music continues]
- [Interviewer] Let's talk about some of those suits.
- Do we have to talk about some of these suits?
There we go.
I mean they were all big and baggy
and that was the look back then.
You go look at any athletes back in the day
and you're gonna see the baggy suits.
These were these old school leisure suits,
you know not meant to wear a collar shirt and a tie with it.
I had a few of those.
When you play for the Yankees,
we had to travel wearing suits and ties,
you know especially during the beginning of my career,
at the end of my career they sort of
relaxed the rules a little bit
so we always wore suits and ties.
But this was, you know
if you wanted to tone it down a little bit,
you'd go with these old leisure suits
with the dress t-shirt.
I think probably you talk about
evolving over time,
one of the most uncomfortable things for me
was to go from these baggy suits to tailored suits.
And my wife deserves credit for that
because I wanted no part of it.
[upbeat music]
I wouldn't say I obsess over watches like a lot of people.
Yeah, I think everyone when they're younger thinks,
you know oh man, I want to have a Rolex at some point
so I had the, I think that one's platinum one
with diamonds around it.
But I didn't obsess over it, so yeah,
I can't help you with that one right there.
But I wouldn't say I've obsessed over it.
Now it's my wife pretty much.
[upbeat music]
- [Interviewer] Let's talk about this GQ cover from 2000.
It was your second GQ cover.
- Yeah, I remember we filmed this down in Miami.
I just remember they tried to recreate a scene
from the Beatles when they came over to the US
so they had us and they had all of these like,
this busload of girls following us down the street.
I mean it was fun cuz you play against these guys every year
so you develop relationships with 'em
and then when we got asked to do it all together,
we couldn't wait.
So we had fun with the shoot.
[upbeat music continues]
- [Interviewer] Fashion Week 2002.
Was this your first fashion week experience?
- Damn, I don't know man.
[Derek chuckling]
You think I would've dressed up
a little more for Fashion Week.
You know, another rule we had
when I first came up with the Yankees is on the road
you couldn't wear jeans,
you had to wear slacks.
That was my look, slacks and a shirt.
Looks like here,
Mo Vaughn got a little more dressed up than I.
Yeah, he used to get after it.
[upbeat music]
- [Interviewer] This was your first World Series win.
This was '96.
How special was that one for you?
- First anything is something you're gonna always remember.
Yeah, I'd never seen that many people
in one place before in my life.
And it's a pretty overwhelming experience
and Yankee fans are the absolute best.
But we got millions of fans
hanging from light poles and windows.
It was trees, climbing trees.
It was really was unbelievable
and I can try to explain it
but unless you are there,
there's really no way to even articulate it.
[upbeat music continues]
Damn, how about that man, on the left,
the long leather trench coat.
That may be the last time I wore it matter of fact.
It was a lot of misses with the sunglasses for me
and these pictures I see,
the little small oval shaped sunglasses.
My wife gets on me quite a bit
when she sees these old pictures
and you know, you think it's cool at the time but yeah man.
I have no idea where the footage is, it's lost, no clue.
And I'm so disappointed in that.
I was moving a few years back
and I thought maybe I would find it when we were moving
but have no idea where it is.
[upbeat music]
- [Interviewer] This was after the 2009 World Series win.
- See, I still, still failed with the glasses.
The hair's starting to come down a little bit.
I lost the leather trench coat
and went with the Yankee hoodie and jacket,
which makes sense.
But yeah, see I'm starting to evolve.
The evolution, my style evolution.
That's why we're here, right?
[Derek chuckling]
It had been a long time since we'd won.
We hadn't won in nine years.
And it just goes to show you how hard it is to do.
So, man, that felt good
to get back to the World Series and win.
I don't wanna say you forget
what it feels like
but you need to be reminded of what it feels like.
[upbeat music continues]
- [Interviewer] Here you are with the boss,
George Steinbrenner.
How did his ownership style inspire yours?
- You know what he's, it's funny.
He's has a collared shirt on here.
He used to always wear his turtleneck,
his blazer and a turtleneck.
And this was in Florida.
He'd do it in spring training
and it's a hundred degrees
and he's walking around with a turtleneck
and a sport coat on.
He, in my opinion, one of the best owners
in any sport in the history of sports.
Learned quite a bit from him and his mental approach.
[upbeat music]
- [Interviewer] This is you in Cooperstown,
at your Hall of Fame induction ceremony.
- I see how you guys just left out about 15 years
so you couldn't even show us evolution.
It's just bam, one extreme to the next.
But no, this is,
I'm much more comfortable,
I don't wear a lot of ties anymore.
You know, I'm sort of go a little bit more relaxed.
But when you wear a tie,
it's for a special occasion
and it doesn't get any more special than this.
I remember getting a chance to
share it with family, friends,
who are all a part of my development
into not just the player I was
but the person that I became.
And to get a chance to share that moment with all of them,
it means so much more than any game
you can play on the field.
You know, there's a lot of people responsible for it,
success and I was fortunate to have a lot of 'em there.
[upbeat music continues]
This is Derek Jeter.
Thanks guys for watching my style evolution
and we'll see you next time.
[upbeat music continues]