Iconic Looks That Made History (And How to Recreate Them Today!)

Some outfits aren’t just fashion statements—they’re pieces of history. From Audrey Hepburn’s little black dress to Princess Diana’s effortlessly cool street style, certain looks have defined entire generations.

But here’s the best part: you don’t need a Hollywood budget to recreate them! With a little creativity, some thrift-store hunting, and the right styling tricks, you can bring these timeless fashion moments into your own wardrobe.

Let’s explore seven legendary outfits and how you can make them work for your everyday style.

1. Audrey Hepburn’s “Breakfast at Tiffany’s” Little Black Dress

Why It’s Iconic:
Audrey Hepburn’s black Givenchy dress, pearl necklace, and oversized sunglasses from Breakfast at Tiffany’s is the epitome of timeless elegance.

How to Recreate It:
✔ Find a sleek, well-fitted little black dress (LBD) with a simple silhouette.
✔ Pair it with a pearl necklace (faux pearls work just as well!).
✔ Add black ballet flats or kitten heels for that effortless Audrey charm.
✔ Complete the look with oversized sunglasses and an updo.

Pro Tip: Keep the makeup minimal, with soft eyeliner and a nude lip, to stay true to Audrey’s classic aesthetic.

2. Princess Diana’s Casual Chic Sweatshirt & Biker Shorts

Why It’s Iconic:
Long before the athleisure trend, Princess Diana was effortlessly pairing oversized sweatshirts with biker shorts for a casual yet sophisticated vibe.

How to Recreate It:
✔ Grab an oversized sweatshirt (bonus points if it’s a vintage college or sports logo).
✔ Pair it with black biker shorts for a sporty, streamlined silhouette.
✔ Finish with white sneakers and tube socks for that 90s feel.
✔ Throw on retro sunglasses to capture Diana’s effortless cool.

Pro Tip: Tuck your hair into a baseball cap for extra “off-duty royal” vibes.

3. Marilyn Monroe’s White Halter Dress

Why It’s Iconic:
The billowing white halter dress from The Seven Year Itch is one of the most famous fashion moments in history.

How to Recreate It:
✔ Find a white fit-and-flare dress with a halter or plunging neckline.
✔ Pair with strappy heels or classic pumps.
✔ Style your hair in soft, voluminous curls.
✔ Wear red lipstick to channel that vintage glamour.

Pro Tip: Not comfortable in white? A pastel or floral halter dress can give the same retro aesthetic with a modern twist!

4. Jackie Kennedy’s Timeless Pink Suit & Pillbox Hat

Why It’s Iconic:
Jackie O’s pink Chanel suit is still one of the most recognisable outfits in political and fashion history.

How to Recreate It:
✔ Look for a structured pastel blazer and matching skirt.
✔ Add pearls and white gloves for extra sophistication.
✔ Carry a small, structured handbag for a polished finish.
✔ If you’re feeling bold, complete the look with a pillbox hat.

Pro Tip: Swap the skirt for matching tailored trousers to bring this vintage look into the modern era.

5. Cher’s Sheer Beaded Gown (Met Gala 1974)

Why It’s Iconic:
Before the “naked dress” trend, Cher stunned in a sheer, glittering Bob Mackie gown that redefined red carpet fashion.

How to Recreate It:
✔ Opt for a sheer or mesh top with intricate beading or sequins.
✔ Layer with a nude slip or fitted bralette for coverage.
✔ Pair with high-waisted trousers or a maxi skirt to balance the boldness.
✔ Go all out with bold, feathered accessories if you’re feeling daring!

Pro Tip: If sheer isn’t your thing, choose a shimmery, form-fitting maxi dress to channel Cher’s signature sparkle.

6. Madonna’s 80s “Like a Virgin” Look

Why It’s Iconic:
Madonna’s lace, corset, and layered jewellery from her Like a Virgin era set the standard for rebellious 80s fashion.

How to Recreate It:
✔ Start with a white lace bodysuit or corset.
✔ Layer with a tulle skirt or high-waisted shorts.
✔ Stack on chunky cross necklaces, pearls, and fingerless lace gloves.
✔ Finish with messy curls and a bold red or pink lip.

Pro Tip: Oversized blazers and lace socks can add an everyday wearable touch to this bold look!

7. Rihanna’s 2015 Met Gala Yellow Cape Gown

Why It’s Iconic:
Rihanna’s stunning yellow Guo Pei cape stole the show at the Met Gala, proving that fashion is art.

How to Recreate It:
✔ Look for a statement coat or cape in a bold colour (yellow, red, or gold).
✔ Pair with a simple, elegant dress underneath to let the outerwear shine.
✔ Add gold accessories and sleek heels for extra drama.
✔ Wear your hair in a sleek updo or loose waves for a polished finish.

Pro Tip: Even a long, dramatic trench coat can give the same high-fashion feel without breaking the bank!

Final Thoughts: Channel Iconic Fashion with a Modern Twist!

You don’t need a designer wardrobe to dress like a style icon. The key is to capture the essence of these famous looks while making them work for your own personality and budget.

Key Takeaways:
Invest in timeless wardrobe staples (like a little black dress or classic blazer).
Accessorise! The right pearls, sunglasses, or gloves can transform an outfit.
Mix old and new—pair vintage finds with modern pieces for a unique take.
Confidence is everything! No outfit is iconic without the attitude to match.

Which of these legendary fashion moments would you love to recreate? Let me know your favourites!