12 Retro Looks That Never Age
Look, I’m gonna be real with you – I’ve spent way too many hours scrolling through vintage fashion photos, and honestly? Some looks just hit different. While everyone’s chasing the latest TikTok trend that’ll be dead in three months, there are certain retro styles that have been making people look effortlessly cool for decades. And trust me, I’ve tried most of these myself (with varying degrees of success :/). Click here to level up your fashion game → What suits on you!
1. The Classic Red Lip
Nothing says timeless like a perfectly applied red lip. I don’t care if you’re channeling Marilyn Monroe or Taylor Swift – this look transcends generations for a reason. The trick isn’t finding the “perfect” red (spoiler alert: there isn’t one), it’s finding YOUR red.
Here’s what I’ve learned from years of red lip disasters:
- Matte formulas last longer but can be unforgiving
- Cream formulas are more comfortable but need touch-ups
- Always line your lips first – trust me on this one
The beauty of the red lip is its versatility. Pair it with minimal eye makeup for that effortless French girl vibe, or go full glam with winged liner. Either way, you’re guaranteed to look put-together even if you rolled out of bed five minutes ago.
2. High-Waisted Everything
Remember when low-rise jeans tried to make a comeback? Yeah, we collectively said “no thanks” and kept our high-waisted pieces. High-waisted bottoms are the ultimate figure-flattering hack that’s been working since the 1940s.
Whether you’re rocking:
- High-waisted jeans with a tucked-in tee
- A-line skirts that hit at your natural waist
- Wide-leg trousers for that Katharine Hepburn energy
The high waist creates an hourglass silhouette and makes your legs look miles long. Plus, you don’t have to worry about your stomach hanging over your waistband when you sit down – revolutionary concept, right?
3. The Little Black Dress
Coco Chanel really did us all a favor when she introduced this concept. The LBD is like the Swiss Army knife of fashion – it works for literally everything. I’ve worn mine to job interviews, dates, funerals, and cocktail parties. Same dress, different accessories.
What makes an LBD timeless:
- Simple silhouette that doesn’t scream a specific decade
- Quality fabric that drapes well and doesn’t wrinkle easily
- Flattering fit that makes you feel confident
The secret sauce? It’s not about finding the most expensive one – it’s about finding one that fits your body perfectly and makes you feel like you could conquer the world.
4. Cat-Eye Sunglasses
Ever wonder why cat-eye sunglasses keep coming back? They’re basically face contouring in accessory form. The upswept corners lift your features and add instant glamour to any outfit.
I’ve collected vintage cat-eyes for years, and here’s what I’ve noticed:
- Smaller frames work better for everyday wear
- Oversized versions are perfect for hiding hangover eyes
- The angle matters – too steep and you look costume-y
Audrey Hepburn knew what she was doing when she made these iconic in “Breakfast at Tiffany’s.” They add sophistication to a basic outfit and make you look mysterious even when you’re just buying groceries.
5. Rolled-Up Sleeves and Cuffs
This might seem basic, but hear me out. The rolled sleeve is the easiest way to make any outfit look more intentional. It’s been a style staple since the 1950s, and there’s something inherently cool about it.
The psychology behind it:
- Shows you’re ready to get things done
- Adds visual interest to plain pieces
- Creates better proportions on oversized pieces
FYI, there’s actually a right way to roll sleeves – you want them to sit just below your elbow, not bunched up at your wrist like you’re about to do dishes.
6. The Leather Jacket
If you don’t own a leather jacket, are you even trying? This piece has been the ultimate cool-girl essential since Marlon Brando made it iconic in the 1950s. It instantly elevates everything from sundresses to basic jeans and tees.
What to look for:
- Real leather ages beautifully (though quality faux options exist)
- Classic cut without too many bells and whistles
- Proper fit – snug but not restrictive
I’ve had mine for eight years, and it keeps getting better with age. It’s like a fine wine, but for your wardrobe. The beauty is its versatility – throw it over a floral dress to add edge, or pair it with all black for that effortless rocker vibe.
7. White Button-Down Shirt
The white button-down is probably the most versatile piece in fashion history. Seriously, name one outfit it doesn’t improve. I’ll wait.
Style it:
- Tucked into high-waisted bottoms for classic chic
- Tied at the waist over a slip dress
- Layered under sweaters with just the collar showing
- Worn oversized as a beach cover-up
The key is finding one with good structure that doesn’t look like you borrowed it from your dad’s closet (unless that’s the vibe you’re going for, which is totally valid).
8. Winged Eyeliner
Let’s be honest – winged eyeliner is intimidating. But when you nail it? You feel like you could run the world. This look has been making eyes pop since ancient Egypt, with modern variations perfected in the 1960s.
My hard-earned tips:
- Start small – you can always make it bigger
- Use tape as a guide until you get the hang of it
- Liquid liner gives the sharpest lines
- Practice makes perfect (and lots of makeup remover)
The wing elongates your eye shape and adds instant drama. Plus, there’s something satisfying about getting both eyes to match perfectly.
9. Pearl Accessories
Before you roll your eyes and think “grandma jewelry,” hear me out. Pearls have been having a major moment, and honestly, it’s about time. They add instant sophistication without trying too hard.
Modern ways to wear pearls:
- Layered necklaces mixing pearls with chains
- Pearl hair clips for an unexpected touch
- Statement pearl earrings with casual outfits
- Pearl-detailed bags or shoes
The trick is mixing them with contemporary pieces so you don’t look like you’re headed to cotillion. A chunky pearl necklace with a graphic tee? Chef’s kiss.
10. The Trench Coat
Burberry knew what they were doing when they created this masterpiece. The trench coat is practical, polished, and works in literally any weather that isn’t blazing hot or snowing.
What makes it timeless:
- Classic silhouette that flatters every body type
- Neutral colors that go with everything
- Quality construction that lasts for decades
- Versatile styling options
I throw mine over everything from workout clothes to cocktail dresses. It’s like having a chic shield against the world, and the belt creates an amazing hourglass shape.
11. Ballet Flats
Remember when everyone was obsessed with uncomfortable heels? Ballet flats said “not today” and gave us comfort without sacrificing style. Audrey Hepburn and Brigitte Bardot made them iconic, and they’ve never really left.
Why they work:
- Comfortable enough for all-day wear
- Elegant silhouette that elongates legs
- Versatile styling from casual to dressy
- Easy to walk in (revolutionary concept)
The key is finding ones with good arch support and quality materials. Your feet will thank you, and you’ll still look put-together.
12. Vintage-Inspired Prints
Certain prints just never go out of style, and there’s science behind it. Polka dots, stripes, and florals have been fashion staples for over a century because they’re visually appealing without being overwhelming.
Timeless prints include:
- Polka dots in classic black and white
- Breton stripes for that effortless French vibe
- Small floral prints that aren’t too busy
- Gingham for a sweet, retro touch
The secret is choosing prints that complement your personal style rather than overwhelm it. A polka dot blouse with solid bottoms hits different than head-to-toe pattern mixing.
The Bottom Line
Here’s the thing about retro looks – they’ve survived decades of fashion cycles for a reason. While trends come and go faster than my motivation to work out, these classic pieces and styling tricks have proven their staying power.
The beauty of incorporating retro elements isn’t about looking like you’re headed to a costume party. It’s about cherry-picking the best elements from past decades and making them work for your modern lifestyle. IMO, the most stylish people aren’t slaves to trends – they’re smart enough to recognize what works and stick with it.
So next time you’re stressing about keeping up with the latest micro-trend, remember that sometimes the most fashionable thing you can do is embrace what’s already been proven to work. After all, if it was good enough for Audrey, Grace, and Marilyn, it’s probably good enough for us 🙂
