Derek Jeter Breaks Down His Most Iconic Looks | GQ Sports Style Hall of Fame

[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.

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[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.

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[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.

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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.

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[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.

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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.

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[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.

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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.

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[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.

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[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.

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[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.

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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.

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[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.

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[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.

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[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.

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