When it comes to style decades, the 1990s holds an unshakable magic—a blend of comfort, cool, and rebellion that strikes a chord whether you lived through it or are just discovering its charm. Watching Matt Santiago’s “get ready with me” video brought a rush of nostalgia and inspiration. As someone who’s lived through (and still loves) the era of Levi’s, Tommy Hilfiger, and Dr. Martens, let me walk you through how to build an authentic 90s style outfit—from top to toe, plus a few tips drawn from years of sifting thrift racks and learning style lessons the fun way.

Start with the Denim: Levi’s 505 Jeans

Why 90s Denim Still Rules

You can’t talk about a 90s style outfit without paying tribute to classic denim. Levi’s 505 jeans are the dream here:

Fit & Style: Slightly relaxed, straight through the leg, and not too low-rise. The 505s fall perfectly in that sweet spot between baggy and fitted.
Fabric & Feel: 100% cotton gives that rugged beauty—jeans that feel even better after a few washes and years of roam. I remember finding my first pair at a yard sale; even a decade later, they still held their shape and unique worn-in fades.
Size & Stretchiness: Go true to size if you like a clean look, or up a size for a more authentic, slouchy vibe. If you find a pair in the men’s section, don’t hesitate to try them regardless of your gender—90s fashion loved bending rules.

The Top: Vintage Tommy Hilfiger Polo

Nothing says “90s” quite like the iconic red, white, and navy Tommy Hilfiger logo. Matt’s pick—a vintage Tommy Hilfiger polo—is a move after my own fashion heart. Here’s why:

Brand & Legacy: Tommy Hilfiger polos and shirts carried mega influence in the 90s, known for bold colors, big logos, and a preppy vibe twisted with a streetwear edge. If you’re lucky enough to snag one with the old tag or flag patch, you’re wearing a piece of history!
Fit and Care: 90s polos are typically cut looser. I like to tuck them into high-waisted jeans, just as Matt suggests, for that authentic put-together-but-relaxed silhouette. They’re easy to care for: machine wash and hang dry to preserve color, especially for those precious vintage finds.

Accessories: Small Touches, Big Impact

Fragrance: Blackwater Sports

Matt highlights Blackwater Sports—an affordable, timeless scent. I love when a fragrance can evoke a mood instantly. In the 90s, you didn’t need to break the bank to smell great. Wear something sporty and fresh for that unmistakably youthful energy.

Watches and Jewelry

Cardi Watch: Think of this as your statement timepiece—a simple watch, maybe a bit chunky or square-faced. It doesn’t need to be expensive; vintage shops and market stalls are treasure troves.
Silver Bracelet & Eyewear: Don’t neglect these touches! In my 90s days, a classic silver chain or bracelet and oval or rectangle wire-frame sunglasses gave instant cred. If you can find vintage eyewear—even better.

Footwear: Dr. Martens & White Socks

Dr. Martens: These classic boots are the symbol of subculture cool. They’re sturdy, can handle a little scuff, and get even better with age. I wore the same pair from high school into my twenties—battle scars and all.
White Socks: Never skip the socks! Pull up some crisp, ribbed white athletic socks with Docs. It’s a detail that telegraphs “I know the vibe” without even trying.

Why 90s Style Still Matters to Me (And Maybe To You)

My love affair with 90s style is about more than just nostalgia. There’s a sense of possibility and experimentation—no fashion apps, just gut instinct and trial and error. Sometimes that meant accidental color clashes or surprise trends, but it always meant self-expression.

A 90s style outfit is, at its core, about pieces that last:

Denim that weathers every adventure.
Brands like Tommy Hilfiger that become part of your story.
Shoes (like Dr. Martens) that walk you through every phase of life.

When I build a look inspired by this decade, I feel a jolt of confidence—like I’m ready for a night out with friends, a concert, or just a slow wander through the city. The best part? Every piece can be styled up or down, worn by anyone, and personalized infinitely.

If you’re looking for more outfit ideas or want to explore the vibe of past decades, check out these nostalgia & retro finds and design style inspiration.

Conclusion: Wear It Like You Mean It

At the end of the day, nailing a 90s style outfit is about more than copying what you see in old Polaroids or on TikTok. It’s about confidence, comfort, and tiny details that make your look uniquely yours. Trust your gut, mix vintage and new, and walk tall in those Docs (or whatever makes you feel alive).

The real magic? 90s pieces are forgiving, enduring, and always ready for adventure—just like you. So throw on that Tommy polo, pull up those socks, and let your story show.

What’s your favorite 90s staple—or your best thrift store find? Let’s keep the conversation (and the style) going!

@drellli_ How did I do? #90sthrowback #mfdoom #rapsnitchknishes #fyp #foryou ♬ original sound – Drelli

90s Style, agree? #fyp #foryoupage #foryou #trend #trending #tiktokfashion #fashiontiktok #fashiontiktok #fashionstyle #menstyle #getreadywithme #grwm #ootd

“hey, it’s Saturday today, so let’s get dressed.
for today’s content,
I’m gonna show you what the 90s style looks like.
so let’s make a fit. way back. 90s, they love denim jeans.
that’s why I pulled this out.
this the levi’s 5 o 5
for the top.
I love this top, guys.
there’s the vintage Tommy Hilfiger.
there’s the tag, guys.
as you can see, it’s already vintage.
one thing they do way back at the 90s,
they topped the polo shirt.
for today’s scent,
I’m gonna pull out the Blackwater Sports
because of its affordability
and so Bramble with its price.
what are you waiting for?
click that yellow bag and purchase this product.
for my accessories,
first, the Cardi watch,
my silver bracelet, and a vintage eyewear.
and for my footwear, I’m gonna wear this classic Dr.
Martens. your outfit doesn’t mean anything
if you don’t have white socks.
white socks wear their staple back in their time.
this is the 90s look, guys.
what do you think?”