Dress Exactly Like 90s Men with 15 Celebrity-inspired Outfit Ideas

The 1990s marked a transformative era in men’s fashion, blending rebellious grunge with sleek minimalism and bold streetwear.

This decade saw the rise of oversized silhouettes, relaxed tailoring, and a casual approach to formal wear that continues to influence contemporary style.

From the iconic turtleneck-and-jeans combo popularised by tech visionaries to the laid-back elegance of Hollywood’s leading men, 90s fashion offered a diverse palette of looks that resonate with today’s trend-conscious gents.

This guide delves into 15 celebrity-inspired outfit ideas epitomising 90s men’s fashion.

We’ll explore the signature styles of Brad Pitt, George Clooney, Will Smith, and other trendsetters who defined the decade’s aesthetic.

For each look, we’ll provide insights on recreating these ensembles with modern pieces, enabling you to capture the essence of 90s fashion for your next themed event or to infuse your wardrobe with retro flair.

From double denim to mandarin collar suits and grunge-inspired layers to minimalist tailoring, these outfits encapsulate the versatility and creativity that characterised men’s fashion in the 1990s.

Whether you’re aiming for the rugged charm of Johnny Depp or the polished appeal of Will Smith, this guide offers a comprehensive roadmap to achieving authentic 90s style in the present day.

1. Brad Pitt’s Business Casual

Brad Pitt’s ensemble at the ‘Waterworld’ premiere in 1995 exemplifies the relaxed yet refined approach to business casual that defined 90s menswear.

Pitt sports a muted grey jacket over a crisp white shirt, eschewing the tie for a more approachable look.

This combination balances formal and casual, perfect for office environments and social gatherings.

Opt for an unstructured blazer in a light grey wool blend to recreate this look. Pair it with a white Oxford shirt, leaving the top button undone for a relaxed air.

Choose tailored trousers in a complementary shade, such as charcoal or navy. For footwear, brown leather loafers or derby shoes complete the ensemble.

Modern brands like Reiss, COS, or Suitsupply offer suitable pieces to achieve this timeless 90s aesthetic.

2. George Clooney White Nautical Suit

George Clooney’s 1992 portrait showcases a bold take on the nautical trend, featuring an all-white suit that exudes confidence and sophistication.

This look embraces the 90s penchant for monochromatic outfits and pays homage to classic maritime style.

To emulate Clooney’s daring ensemble, select a white linen or cotton-blend suit with a relaxed fit.

The versatility of the white suit allows for endless styling possibilities, inspiring you to experiment with your look.

The jacket should feature peaked lapels and a double-breasted closure for authenticity.

For a subtle contrast, pair the suit with a white dress shirt and a navy or burgundy silk pocket square and complete the look with white leather dress shoes.

Contemporary brands like Brunello Cucinelli, Ralph Lauren, or Zara offer suitable white suits and separates to construct this striking outfit.

3. Matthew Perry Double Denim With Blazer

Matthew Perry’s 1995 red carpet appearance showcases a quintessential 90s trend: double denim elevated with a blazer.

This look combines casual staples with a touch of formality, reflecting the decade’s propensity for mixing dressy and casual elements.

To recreate Perry’s ensemble, pair a light-wash denim shirt with slightly darker jeans.

The key is to ensure a subtle contrast between the shades of denim. Layer a navy or black single-breasted blazer over the denim shirt.

For footwear, choose black leather Chelsea boots or loafers. Brands like Levi’s, Acne Studios, or Topman offer suitable denim pieces, while retailers like J.Crew or Uniqlo provide affordable blazer options.

4. Will Smith Mandarin Collar Suit

Will Smith’s appearance at the ‘The Devil in a Blue Dress’ premiere in 1995 showcases a sophisticated take on 90s formal wear.

Smith dons a sleek black mandarin collar suit, embodying the decade’s penchant for minimalist yet impactful fashion choices.

To replicate this look, seek a black wool-blend suit with a mandarin collar jacket. The absence of lapels creates a clean, streamlined silhouette characteristic of 90s minimalism.

Pair the suit with a black silk or cotton shirt to maintain the monochromatic theme. For footwear, opt for polished black leather Oxford shoes.

Brands like Paul Smith, ASOS Design, or Topman offer modern iterations of mandarin collar suits.

This ensemble proves ideal for formal events where one wishes to make a subtle yet striking sartorial statement.

5. Johnny Depp’s Oversized Suit & Dagger Collar Shirt

Johnny Depp’s outfit at the ‘What’s Eating Gilbert Grape’ premiere in 1993 epitomises the 90s trend of oversized tailoring combined with distinctive shirt styles.

Depp sports an expansive grey suit paired with a white shirt featuring an exaggerated dagger collar.

To achieve this look, select an oversized grey wool suit with a relaxed fit through the shoulders, chest, and trousers.

The key lies in the deliberate bagginess without appearing ill-fitting. Underneath, wear a white dress shirt with a prominent dagger collar – a style characterised by long, pointed collar tips. Complete the ensemble with black leather dress shoes.

For the suit, explore offerings from Zara, COS, or vintage outlets. Eton and Thomas Pink provide shirts with more pronounced collars.

6. Brad Pitt’s Shawl Collar Sweater & Velour Trousers

Brad Pitt’s off-duty look from 1996 exemplifies casual 90s luxury thanks to the oatmeal shawl collar sweater and rich velour trousers.

To recreate this ensemble, start with a chunky knit sweater in a neutral oatmeal or beige tone, ensuring it features a prominent shawl collar.

Pair this with straight-leg velour trousers in a deep hue like burgundy or forest green. For footwear, brown suede desert boots complement the outfit’s tactile nature.

Brands like J.Crew, Uniqlo, or Mango offer suitable sweater options, while Reiss and Scotch & Soda provide velour trouser alternatives.

This combination yields a comfortable yet refined look for casual winter gatherings or upscale weekend outings.

7. Steve Jobs’ Infamous Turtleneck & Jeans

Steve Jobs’ signature look, as seen in his 1998 and 1999 keynote addresses, became an iconic symbol of 90s tech entrepreneurship.

This minimalist ensemble comprises a black turtleneck paired with blue jeans, embodying the decade’s shift towards functional, no-frills fashion in the burgeoning Silicon Valley.

To emulate Jobs’ distinctive style, select a fine-gauge black turtleneck in merino wool or a cotton-cashmere blend and straight-leg blue jeans in a medium wash.

For footwear, choose grey New Balance 991 trainers, Jobs’ preferred choice. Uniqlo and Marks & Spencer offer quality, affordable turtlenecks, while Levi’s 501 Original Fit jeans provide an authentic 90s silhouette.

8. George Clooney 90s Style Preppy Look

George Clooney’s 1992 portrait session captures the essence of 90s preppy style.

Clooney sports a classic combination of a navy blazer, light blue Oxford shirt, and khaki trousers, demonstrating the enduring appeal of traditional American sportswear.

To recreate this timeless look, begin with a navy wool blazer featuring notch lapels and brass buttons.

Underneath, don a light blue Oxford cloth button-down shirt. Pair these with flat-front khaki chinos.

For footwear, brown leather penny loafers complete the preppy ensemble. Brooks Brothers, J.Crew, and Ralph Lauren offer suitable pieces to construct this outfit.

9. Tom Cruise’s Blazer & White T-shirt

Tom Cruise’s 1993 street style showcases a quintessential 90s casual-cool look.

Cruise pairs a structured blazer with a simple white T-shirt, demonstrating the decade’s penchant for mixing formal and casual elements.

To achieve this stylish ensemble, select a well-fitted black or charcoal wool blazer.

Layer this over a crisp white crew-neck T-shirt, ensuring the tee is high quality and maintains its shape.

Pair with straight-leg blue jeans for an authentic 90s silhouette. For footwear, black leather Chelsea boots add a touch of sophistication.

Reiss and AllSaints offer sleek blazer options, while brands like Sunspel provide luxury basics.

10. Rev Run of Run-DMC’s Formalwear & Adidas Shoes

Rev Run’s ensemble at Muhammad Ali’s 60th birthday party in 2002 exemplifies the late 90s and early 2000s trend of blending high-end formalwear with streetwear elements.

The Run-DMC member pairs a classic black tuxedo with iconic Adidas Superstar trainers, creating a bold juxtaposition that defined the hip-hop fashion of the era.

To recreate this daring look, start with a well-fitted black tuxedo featuring peak lapels. Opt for a white dress shirt and a black bow tie to maintain formal aesthetics.

The key to this outfit lies in the footwear: choose a pair of white Adidas Superstar trainers with distinctive black stripes.

For an authentic touch, wear the trainers without laces, mimicking Run-DMC’s signature style.

Suitsupply and Hugo Boss offer suitable tuxedo options, while Adidas continues to produce the classic Superstar model.

11. George Clooney’s 90s Dad Look

George Clooney’s appearance at the ‘Tommy Boy’ premiere in 1995 captures the essence of the 90s ‘dad’ aesthetic.

Clooney sports a relaxed combination of a leather jacket, light-wash jeans, and a simple shirt, embodying the casual cool that defined off-duty style in the mid-90s.

To emulate this laid-back look, begin with a black leather bomber jacket, ensuring a slightly oversized fit for authenticity, and a plain white or light grey T-shirt.

Pair these with straight-leg, light-wash denim jeans. For footwear, choose black leather lace-up boots or classic white trainers.

All Saints and Schott NYC offer quality leather jackets, while Levi’s 505 Regular Fit jeans provide an appropriate 90s cut.

12. David Beckham’s Oversized Leather Blazer

David Beckham’s 1997 London street style showcases the bold, oversized tailoring trend that dominated late 90s fashion.

Beckham pairs an expansive leather blazer with a simple white T-shirt and trousers, demonstrating the era’s penchant for mixing textures and proportions.

To recreate this striking look, source a black leather blazer with an oversized silhouette and broad shoulders, a boxy cut plain white crew-neck T-shirt, slim-fit black trousers, and black leather Chelsea boots.

Contemporary brands like Balenciaga and Acne Studios offer modern interpretations of oversized leather blazers, while COS and Arket provide suitable basics.

13. Will Smith White Leather Bal Collar Suit

Will Smith’s appearance at the ‘Selena’ premiere in 1997 showcases a bold interpretation of formal wear, characteristic of late 90s red carpet fashion.

Smith dons a striking white leather suit with a distinctive bal collar, exemplifying the era’s penchant for luxurious materials and sleek silhouettes.

To recreate this audacious ensemble, seek a white or high-quality faux leather suit with a bal collar jacket, known as a band collar, creating a minimalist, streamlined look.

Pair the suit with a black silk shirt and polished black leather Oxford shoes for contrast.

While genuine leather suits are rare, ASOS and Topman occasionally offer faux leather alternatives.

Consider a white cotton or linen suit with similar styling for a more wearable interpretation.

14. George Clooney’s Three Piece Suit With T-shirt

George Clooney’s outfit at the 1995 Planet Hollywood opening in San Diego epitomises the 90s trend of subverting formal wear conventions.

Clooney pairs a classic three-piece suit with a casual white T-shirt, creating a juxtaposition that defined the decade’s approach to smart-casual dressing.

To emulate this look, start with a charcoal or navy three-piece wool suit, ensuring a relaxed fit characteristic of the 90s.

Instead of a dress shirt, don a high-quality white crew-neck T-shirt – it should sit smoothly under the waistcoat without bunching and complete the ensemble with black leather Oxford shoes.

Suitsupply and Charles Tyrwhitt offer suitable three-piece suits, while Sunspel provides luxury T-shirts ideal for this pairing.

15. Brad Pitt’s 90s All-Black Look

Brad Pitt’s 50th Annual Writers Guild of America Awards ensemble exemplifies the sleek, monochromatic trend popular in late 90s fashion.

Pitt sports an all-black outfit, combining tailored elements with a casual edge to create a sophisticated yet approachable look.

To recreate this timeless outfit, begin with a black single-breasted suit in a slightly relaxed fit, characteristic of 90s tailoring.

Wear a black silk or cotton dress shirt underneath, leaving the top two buttons undone for a relaxed air. Skip the tie to maintain the casual-formal balance.

For footwear, choose black leather Chelsea boots to add a touch of rock ‘n’ roll edge.

Brands like The Kooples, All Saints, and Reiss offer suitable all-black suiting options.

Conclusion

The 1990s remain a pivotal decade in men’s fashion, characterised by a unique blend of grunge aesthetics, minimalist tailoring, and bold streetwear influences.

This exploration of 15 celebrity-inspired outfits demonstrates the versatility and enduring appeal of 90s men’s style.

From Brad Pitt’s relaxed business casual to Will Smith’s daring white leather suit, these looks offer a comprehensive palette for modern men seeking to incorporate 90s flair into their wardrobes.

Key elements defining 90s men’s fashion include oversized silhouettes, formal and casual pieces juxtaposed, monochromatic ensembles, and a fearless approach to texture and material.

The era’s fashion ethos encouraged individual expression through clothing, a principle that remains relevant in today’s style landscape.

To authentically recreate 90s looks, focus on proportions and fabric choices. Opt for slightly looser fits in suits and trousers, experiment with unexpected pairings like T-shirts under blazers, and don’t shy away from bold choices in colour or texture.

Vintage and thrift shops prove invaluable resources for genuine 90s pieces, while contemporary brands like Acne Studios, COS, and Uniqlo offer modern interpretations of 90s staples.

When adapting these styles for the present day, consider updating the fit slightly for a more current silhouette.

While 90s fashion often embraced baggier cuts, subtle tailoring can make these looks more wearable in contemporary settings. Additionally, pay attention to fabric quality and construction to elevate the overall aesthetic.

Ultimately, the enduring influence of 90s men’s fashion lies in its ability to blend comfort with style and formal elements with casual ease.

By studying and reinterpreting these celebrity-inspired outfits, modern men can infuse their wardrobes with the decade’s iconic cool, creating nostalgic and thoroughly contemporary looks.

Whether dressing for a themed event or simply incorporating 90s elements into everyday wear, these outfit ideas provide a rich source of inspiration for fashion-forward individuals.

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