How to Make a 90s Hip Hop Outfit: Big Denim, Authentic Energy, and a Whole Lotta Swagger

image

If you’ve ever tried to capture the essence of true 90s hip hop fashion, you know it’s more than just throwing on some baggy jeans and calling it a day. There’s heritage, rhythm, and bold self-expression laced into every look. Thanks to Tom Westwood’s candid and spot-on step-by-step breakdown (and speaking as someone who survived the decade in baggy jeans and bomber jackets myself), I’m here to guide you through building your own authentic 90s hip hop outfit—layer by layer.

Primary Keyword: 90s hip hop outfit Secondary Keywords: baggy denim streetwear, vintage hip hop style, 90s fashion essentials

1. Start With Baggy Denim: The Backbone of 90s Hip Hop

Tom’s first—and most critical—rule: start with authentic baggy jeans. In my own teen years, I hunted thrift stores for the baggiest pair of South Pole or Echo jeans, loving how they hovered at the edge of “comically oversized” yet somehow felt so right. Tom’s FUBU pair captures the magic: slouchy, low-slung, ready for the dancefloor or street corner. With room for two people in one leg (not kidding!), baggy jeans are comfort and attitude wrapped up in a single garment.

Where to shop & what to search for:

Pro tip from experience: Never underestimate the power of a good belt—you’ll need it. I still have an old webbed belt I wore almost daily in high school to keep those jeans from hitting the ground.

2. Keep It Simple With a Graphic or Oversized Tee

Once you’ve got your jeans, the next essential is a baggy tee. Tom’s pick is a simple piece from Weekday, but the magic is in the loose, effortless fit. The 90s was all about letting your clothes breathe. Think basic white, bold primary colors, or classic sports logos.

Material & washing:

  • Cotton is your friend—soft, breathable, and ages beautifully.
  • Gentle wash keeps prints and colors fresh for longer.

Fit tip: If you don’t already own oversized tees, just buy a size or two up, or browse vintage racks for authentic fits.

3. Step Into Classic Timberlands (“Tims”)—But Make Them Your Own

Timberlands are a hip hop staple, full stop. Tom’s flex is a rare beige collaborative pair (a dream for any collector), but the classic wheat or black Timbs will do just as well.

Why Timbs matter: They’re tough, durable, and practically scream 90s hip hop royalty. I bought my first pair with saved-up dollars and wore them through every kind of weather. Once broken in, they’re like armor for your feet.

Fit advice: Make sure they’re snug but not tight—leave room for thick socks in winter.

Get more street-ready shoe inspiration here. Sports collection

4. Top It Off: Kangol, Durag, or Bandana

Your headwear is where you show your hip hop allegiance. A Kangol hat, a durag, or even a bold bandana speaks volumes. Tom’s wool Kangol brings classic Slick Rick energy. The first time I put on an old-school bucket hat, I felt like I could command any cypher in the city.

Do:

  • Match your hat to your jacket or go all-out with color contrasts.
  • For real authenticity, let the logo be seen—Kangol kangaroo, anyone?

5. Jewelry: Statement Chains, Pendants, and Rings

From Mercedes pendants to chunky Cuban links, jewelry is where you add individuality to your look. Tom’s Vitali piece and his favorite pendant show that it’s less about price and more about personality. My favorite was a thrifted rope chain that saw every house party and late-night hangout.

Mix & match:

  • Don’t shy from layering chains.
  • Rings, watches, and even a blinged-out pinky ring if you’re feeling fly.

6. Oversized Varsity Jacket or Bomber

Fall (or a chilly summer night) calls for something with presence. 90s hip hop outerwear meant varsity jackets, big bombers, or vintage American college gear. Tom rocks his South Pole jacket, but anything big, bold, and statement-making works. I’ll never forget the oversized black-and-red varsity jacket I begged my brother for until he finally gave in—it made every fit instantly cooler, and still gets compliments.

Try:

7. Finish With That Key Accessory: Rimless or Bold Shades

Nothing completes the look like statement sunglasses. Go for rimless, colored lenses, or anything that says you’re ready to headline a 90s music video. I still wear rimless shades on days when I want to channel my inner Boyz II Men or Aaliyah.

Why I Keep Coming Back to the 90s Hip Hop Aesthetic

Sure, fashion changes—but the 90s hip hop outfit is about more than what you wear. It’s about confidence, movement, and belonging. Every piece you pick tells a story—where you found it, how you wore it, the way it made you walk taller. I’ve watched these looks come back with a vengeance, and it never feels like a costume when you style it your own way.

Conclusion: Your Own 90s Hip Hop Story

Building a 90s hip hop outfit is equal parts art and attitude. Gather your baggy denim, step into those Tims, crown your look with headwear, and layer on those varsity jackets and chains. Most importantly: wear it like you mean it. The best 90s outfits are a mix of authenticity, creativity, and a whole lot of fun.

Ready for your own throwback? Browse vintage-inspired and trending pieces here, and remember—swagger never goes out of style. Peace!

@west_t_wood How to make a 90s Hiphop outfit #fashion #90s #hiphop ♬ original sound – Tom Westwood

Follow
How to make a 90s Hiphop outfit #fashion #90s #hiphop

“Yo, let’s talk about 90s outfits
cause everyone seems to get this wrong.
First off, you need some baggy denim.
These are FUBU.
If you don’t know where to shop for baggy denim,
check vintage depop, eBay.
The main things you wanna search for are FUBU,
South Pole, Echo,
Rockaway, G Star,
those sorts of brands.
Anyone actually owns baggy jeans
and wears baggy jeans on the regular,
you’ll know that a bell is your best friend.
You can literally
get me and my girlfriend in these jeans.
Next step. This step,
I’m just gonna throw in a bag of tea.
This one’s from Weekday. Simple.
Get it from anywhere.
It doesn’t really matter
to be honest.
Step 3 to get you a nice look
is you need a pair of Tims.
These are a collab with a brand of cold wool,
and they’re like
the only beige Tims I have. I know
I probably look ridiculous with this thing on right now,
but it’s comfy
and it stops my hair,
like, drying out when I’m sleeping.
Onto headwear,
nice. Hip hop especially,
you gotta go with a tangle.
So what, this 5:04 wool tangle,
lowkey this is the vibe.
I feel like Slick Rick or something in this.
Don’t know what that was.
Tangles on. Step forward, jewellery.
I’m gonna go with these
patching from Vitali right here.
Also this little Mercedes pendant,
just cause I think it looks kinda cool.
It’s getting a bit colder,
so I’m gonna Throw on a jacket. 90s,
you wanna go for an oversized looks.
An oversized varsity jacket.
Couple brands to look out for.
To name a few
is Rockwear, South Pole,
which is literally what I’m wearing right now.
Boo. Boo. Any vintage,
like American College
or uni, like
Varsity Jacket,
that works, too.
Now, for me personally,
I’m gonna go with these 90s rimless shades, because.
Do I need to say anything else?
Okay, so this is how you make an artist outfit.
Let me know what you think in the comments.
I feel like I should be part of boys to men,
you know? Boys to men.
If you’re listening,
if you’re watching this,
take it. Applications.
I’ll send mine across. Peace.”