Television has a way of creating style icons. Sometimes it’s the glamorous, high-fashion moments that stick with us, but more often, it’s the casual, everyday outfits that truly define a character. These are the looks that feel attainable, relatable, and effortlessly cool. They tell a story about who the character is when they’re not saving the world or closing a big deal. For those of us with a love for vintage-inspired style, these on-screen wardrobes are a goldmine of inspiration.

From the cozy knits of the 90s to the sharp, off-duty polos of the 60s, TV characters have provided a masterclass in casual dressing for decades. These looks are memorable because they have personality and authenticity. Let's break down some of the most iconic casual outfits from popular TV characters and explore how you can bring their signature style into your own wardrobe with a modern, vintage-inspired twist.

Chandler Bing’s 90s Relaxed Fits - Friends

Could his wardrobe be any more iconic? Chandler Bing was the undisputed king of 90s casual layering. His style was a comfortable, slightly oversized mix of sarcasm and knitwear. It was all about relaxed silhouettes, bowling shirts, and, of course, the legendary sweater vest. His look was approachable and perfectly captured the laid-back aesthetic of the decade.

Chandler’s style feels so relevant today because it taps into the resurgence of 90s fashion. It’s all about comfort without sacrificing personality. He showed that you could look put-together without being formal, relying on interesting textures and layers to create a memorable outfit.

How to Get the Look:

  • The Sweater Vest: The cornerstone of Chandler's wardrobe. To modernize it, look for a vest with a slightly slimmer fit, not a billowy one. Wear it over a simple white or black t-shirt for a casual look, or layer it over a relaxed-fit button-down for a more classic feel. Neutral colors like navy, grey, or brown are the most versatile.
  • The Bowling Shirt: Another Chandler staple. These short-sleeve, button-up shirts, often with vertical stripes or retro patterns, are perfect for a relaxed summer look. Pair an open bowling shirt with a plain tee, some straight-leg jeans, and classic sneakers.
  • The Relaxed-Fit Chinos: Ditch the skinny pants. Chandler often wore pleated, relaxed-fit chinos in khaki or olive. This silhouette is back in a big way. Find a pair that gives you room to move and cuff them at the ankle to show off a cool pair of socks and your favorite loafers or retro sneakers.

Don Draper’s Off-Duty Style - Mad Men

While Don Draper is famous for his razor-sharp suits, it’s his off-duty style that offers a masterclass in sophisticated, casual menswear. When he wasn’t in the boardroom, Don’s look was clean, classic, and effortlessly masculine. His weekend wear often consisted of sharp polo shirts, slim-fit trousers, and classic cardigans—all hallmarks of 1960s suburban cool.

Don’s casual style is memorable because it’s so polished. It proves that you can be comfortable without being sloppy. Each piece was simple, high-quality, and perfectly fitted, creating a look of quiet confidence.

How to Get the Look:

  • The Knit Polo: Forget the standard pique cotton polo. Don Draper favored knit polos, which have a softer drape and a more luxurious, vintage feel. Look for polos with a classic three-button placket and a sharp collar. Tucking a knit polo into a pair of tailored trousers or chinos is a simple way to achieve that mid-century sharpness.
  • The Camp-Collar Shirt: For his trips to California, Don embraced the breezy camp-collar shirt. These shirts, with their open, notch-lapel-style collar, have a relaxed yet refined vibe. Go for a solid color or a subtle plaid pattern and wear it untucked with slim-fit trousers or shorts.
  • The V-Neck Cardigan: A simple, fine-gauge V-neck cardigan in a neutral color like grey or navy was a key layering piece for Don. He’d wear it over a button-down shirt for a look that was perfect for lounging at home or a casual dinner. It’s a timeless way to add a layer of warmth and sophistication.

Steve Harrington’s Effortless Throwback Cool – Stranger Things

Steve Harrington doesn’t just defend Hawkins from supernatural threats; he also delivers some of the best laid-back looks on TV. His casual style channels classic 1980s Americana with a modern twist, making him a standout for any guy who wants timeless, approachable vibes. Think perfectly faded denim, retro sneakers, and hair that’s become legendary in its own right.

Steve’s outfits are memorable for their blend of confidence and ease. With a few well-chosen staples, you can tap into that same relaxed attitude—ideal for weekends, hangouts, or anytime you want that retro cool without looking like you’re headed to a costume party.

How to Get the Look:

  • The Denim Jacket: Steve’s signature piece is the light-wash, slightly worn-in denim jacket. Look for a classic trucker fit—slim but not tight—with vintage details like metal buttons and chest pockets. Throw it over a neutral tee or hoodie for an effortless layered look.
  • The Striped or Logo Tee: Underneath, he often rocks striped tees or retro-inspired graphic shirts. To keep it current, go for bands, surf motifs, or faded athletic prints.
  • Straight-Leg Jeans: Steve keeps it classic with straight-leg, mid-wash jeans—think Levi’s 505s or 501s. Tuck in your tee or leave it out for a relaxed effect.
  • Retro Sneakers: His footwear of choice? Crisp white sneakers with a subtle pop of color. Canvas high-tops or vintage running shoes work perfectly.
  • Finishing Touch: Optional but recommended—a tousled, voluminous hairstyle (hair product and a little confidence required).Jim’s outfits stand out because they feel authentic and adaptable. You can transition straight from the office to weekend plans without missing a beat. His look is a testament to the power of clean basics and minimal fuss.

How to Get the Look:

  • The Oxford Shirt: Jim lived in classic, button-front Oxford shirts in pale blues, whites, and the occasional subtle check. For a modern take, choose a tailored fit that skims the body—not too tight, not too baggy. Roll up the sleeves for a laid-back vibe.
  • The Slim Khaki Pant: Instead of heavy dress trousers, Jim favored slim or straight-leg khakis in neutral tones like tan or navy. They're business casual done right and translate easily to any setting.
  • Classic Sneakers: While you might spot him in simple dress shoes at the office, Jim sometimes swapped them out for a clean pair of low-profile sneakers on more casual days. Look for minimalist styles in white or grey.
  • Effortless Layering: When it got chilly, Jim reached for a lightweight sweater or a zip-up vest. Stick with neutral shades that keep the outfit grounded.
  • Jim’s style is all about keeping things simple, clean, and versatile. With a few quality basics, you can channel his approachable vibe any day of the week.

The small screen has always been a source of style inspiration, and these characters show that a memorable casual look is about more than just clothes—it’s about personality. Whether you’re drawn to the cozy layers of Chandler Bing, the polished simplicity of Don Draper, or the bold retro fun of Steve Harrington, you can take cues from their iconic wardrobes to enhance your own. It's all about finding those classic, vintage-inspired pieces and wearing them with a confidence that is all your own.