Ultimate Yuppie Style Guide to Master the Affluent Look

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What is Yuppie Style?

Yuppie style is a unique way of dressing that combines peak lapels and double-breasted business suits worn by 1980s Wall Street bankers with garments, footwear, and accessories characteristic of East Coast recreational activities, depicting one’s affluence and entrepreneurial qualities.

Yuppie Style

Yuppie Style Origin

The Yuppie style has roots in British bespoke tailoring and Preppy aesthetics.

Considered the uniform of people working in finance and emblematic of capitalist success, the peak lapels and double-breasted business suits followed strict Savile Row patterns and cuts.

On the other hand, the style’s choice of polo shirts, trench coats, cable-knit sweaters, and straight-leg chinos has roots in the Preppy fashion style, particularly the East-Coast subculture and country club activities.

How to Dress Yuppie?

To master the Yuppie style, one must be well-versed in two essential aesthetic roots: British bespoke tailoring, epitomized by Savile Row designs, and the East Coast Preppy style, focusing on country club leisurewear.

As such, the main garments, footwear, and accessories comprising any Yuppie outfits must be aesthetically relevant and sourced from clothing brands that epitomize the Yuppie ethos.

Yuppie Style Clothing

1. Contrast Collar Tailored Shirt

With aesthetic roots in British bespoke tailoring, contrast collar shirts exude corporate sophistication, making them suitable for office boardrooms and upscale networking events.

Best for: Office boardrooms, high-stake business events

Recommended Brands: Thomas Pink, Hawes & Curtis

Executive Contrast Collar Tailored Shirt Pink Executive Contrast Collar Tailored Shirt

2. Pinstripe Double-breasted Suits

Stemming from 1980s Wall Street attire inspired by British tailoring traditions, pinstripe double-breasted suits are the epitome of financial prowess and suited for high-stakes business meetings or formal events.

Best for: Business meetings and very formal events.

Recommended Brands: Giorgio Armani, J Crew, Theory

Theory Pinstripe Double-breasted Suit J Crew Pinstripe Double breasted Suit

3. Burberry Trench Coat

With aesthetic roots in British military wear, Burberry trench coats are an outer layer in the Yuppie style used during casual business events, after-work cocktails, or weekend getaways.

Best for: Casual business events and after-work cocktails

Recommended Brands: Burberry

Burberry Trench Coat Burberry Trench Coat

4. Cable-knit V-neck Sweater

Inspired by the East Coast leisurewear and country club attire, cable-knit V-neck sweaters are core Yuppie garments for casual Fridays, weekend brunches, and yacht activities.

Best for: Preppy lifestyle events like golf, horse riding, yachting

Recommended Brands: Polo Ralph Lauren

Polo Ralph Lauren Cable-knit V-neck Sweater Polo Ralph Lauren Cable-knit V-neck Sweater

5. Straight-leg Jeans

Inspired by classic American workwear, indigo straight-leg jeans confer Yuppie outfits with casual counterpoint to tailored pieces, making them well-suited for laid-back office environments, weekend outings, and casual dining.

Best for: Art gallery or museum visits and casual dining with friends.

Recommended Brands: Levi’s

Levi's Straight-leg Jeans Levi's Straight-leg Jeans

Yuppie Style Footwear

1. Derby Shoes

Derby shoes have aesthetic origins in British formal footwear and are critical to the Yuppie style in conveying traditional elegance during business presentations or formal dinners.

Best for: Business events and formal dinners.

Recommended Brands: Church’s

Church's Derby Shoes Derby Shoes

2. Low-top White Sneakers

The low-top white leather-style sneakers with aesthetic roots in classic tennis shoes are trendy among Yuppies and used to convey a casual yet polished look.

Best for: Relaxed office environments and weekend brunches at upscale cafes.

Recommended Brands: Common Projects, Adidas Originals

Common Projects Low-top White Sneakers Adidas Original Low-top White Sneakers

3. Court Heels

Yuppie court heels have a low-cut front, a pointed toe, and a stiletto heel, with aesthetic roots in aristocratic footwear worn in the royal courts of the United Kingdom.

Best for: Formal business events, high-profile receptions, and upscale dining engagements.

Recommended Brands: Manolo Blahnik, Jimmy Choo.

MANOLO BLAHNIK Black Court Heels Jimmy Choo Court Heels

Yuppie Style Accessories

1. Red Poka Dot Ties

With roots in the neckties of London’s Jermyn Street – renowned for high-end bespoke tailoring – Red Polka Dot ties are a Yuppie staple used to convey affluence and attention to detail.

Best for: Board meetings and private dinners.

Recommended Brands: Paul Smith, Ralph Lauren

Paul Smith Polka Dot Tie Ralph Lauren Polka Dot Silk Tie

2. Suspenders

Inspired by vintage menswear braces from the early 20th century, suspenders are a quintessential Yuppie accessory that confers any outfit with a touch of Old Money style sophistication.

Best for: Formal charity events and upscale cocktail parties.

Recommended Brands: Albert Thurston, Trafalgar

Trafalgar Suspenders Trafalgar Suspenders

3. Check Plaid Scarves

Check, checked, or chequered plaid scarves have aesthetic origin in Scottish tartans and tweed patterns and are used in the Yuppie style to convey refined sophistication.

Best for: Autumn/winter city strolls and outdoor events

Recommended Brands: Burberry, Barbour

Burberry Check Plaid Scarf. Barbour Check Plaid Scarf

4. White Socks

With roots in American Preppy sports activities, white socks in high-quality materials like Pima cotton or Merino wool are a Yuppie staple in casual and semi-formal settings.

Best for: Relaxed office environments, cafes, and gallery openings.

Recommended Brands: Calvin Klein, Ralph Lauren, Falke

Ralph Lauren White Socks Ralph Lauren White Socks

4. Pearl Jewelry

With origins in traditional European high society and upper-class American circles, pearls are the epitome of indulgence in the Yuppie style.

Best for: Theater, opera, formal dinners.

Recommended Brands: Mikimoto, Tiffany & Co., Cartier

Tiffany Pearl Tiffany Pearl

3 Key Takeaways

  1. Understanding the Yuppie style means recognizing its complex aesthetic roots: a fusion of traditional British tailoring and East Coast Preppy leisurewear.
  2. From double-breasted pinstripe suits and contrast-collar shirts to leather derbies and pearl jewelry, each garment must portray a lifestyle of affluence and taste.
  3. Wearing relevant clothing brands like Brooks Brothers and Ralph Lauren to Tiffany & Co. and Mikimoto is essential to pull off this sophisticated look, whether stepping into a high-stakes business meeting or attending a weekend brunch at an upscale café.

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Similar Styles to Yuppie

Professional Styling Advice

Are you looking to improve your fashion style and unsure where to start? Are you into relaxed-casual, E-girlY2K, or VSCO looks, but Yuppie style resonates with you, and you wonder why?

Contact The VOU’s Style Experts to receive your free and personalized styling advice based on your current way of dressing, preferred outfits, colors, aesthetics, age, gender, body shape, location, and event you seek to attend.

Your dedicated stylist will meticulously select essential garments, footwear, and accessories to craft a wardrobe that complements and enhances your style.

Take advantage of this unique opportunity to experience a transformative fashion adventure, all at no cost to you.

After years of managing hundreds of fashion brands from London's office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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