How To Style Oversized Sunglasses With Updos Without Looking Costumed

Oversized sunglasses have long been a symbol of glamour, mystery, and effortless cool. Paired with an updo, they can elevate your look from everyday casual to editorial elegance. But there’s a fine line between fashion-forward and costume-like. Too often, the combination of bold frames and slicked-back hair veers into retro impersonation or red-carpet caricature territory. The key isn’t avoiding the trend—it’s mastering balance, proportion, and context.

With the right approach, you can wear oversized shades with an updo and still look modern, grounded, and authentically stylish. This guide breaks down exactly how to achieve that equilibrium, offering practical styling rules, common pitfalls, and insights from fashion professionals who shape trends behind the scenes.

Understand the Visual Weight of Oversized Frames

Oversized sunglasses dominate the face. Unlike smaller, minimalist frames, they draw immediate attention and can visually unbalance a look if not styled intentionally. When paired with an updo—which exposes more of the face and neck—the contrast becomes even more pronounced. Without careful coordination, the effect can appear theatrical rather than tasteful.

The goal is harmony: the glasses should complement the hairstyle, not compete with it. Think of them as accessories that enhance your features, not mask them. Start by assessing the proportions of your face and the frame size. A large, cat-eye silhouette might suit someone with strong cheekbones but overwhelm softer facial structures unless balanced with the right hairstyle texture or clothing neckline.

Tip: Hold different sunglass styles up to your face in natural light before committing. If the frame extends beyond the outer corners of your eyes, it's likely oversized—use this as a cue to keep the rest of your look understated.

Choose the Right Updo for Your Frame Shape

Not all updos work equally well with oversized sunglasses. Sleek, tightly pulled styles like a high bun or severe chignon can amplify the dramatic effect of large lenses, sometimes tipping the look into costume territory. Instead, opt for updos with subtle texture, volume, or slight imperfection to soften the overall aesthetic.

• Low messy chignon: Adds sophistication without rigidity. The relaxed texture balances the structured lines of bold frames.
• Braided crown twist: Keeps hair off the face while introducing organic movement that counters the sunglasses’ sharpness.
• Loose top knot: Slightly undone pieces around the temples help integrate the glasses into the look naturally.
• Twisted half-up style: Preserves some face-framing strands, creating a transitional zone between skin and sunglasses.

Avoid overly polished styles unless you’re dressing for a formal event or photo shoot. For everyday wear, a touch of “undone” elegance keeps the ensemble feeling current and wearable.

“Modern styling is about controlled asymmetry. A slightly imperfect updo with oversized sunglasses says you care about fashion—but you’re not trying too hard.” — Lena Torres, Celebrity Stylist & Runway Consultant

Balance Proportions with Clothing and Accessories

Your outfit plays a crucial role in grounding the sunglasses-updo combo. Oversized frames already command attention; pairing them with a busy print, statement necklace, or dramatic shoulder detail can overload the visual field.

Instead, lean into minimalist silhouettes. A clean-line trench coat, a crisp white button-down, or a simple slip dress provides a neutral backdrop that lets the sunglasses shine—literally and stylistically. Necklines matter too: V-necks or scoop necks elongate the torso and balance the vertical emphasis created by exposed necks and tall frames.

Outfit Choice	Works With Oversized Sunglasses + Updo?	Why
Structured blazer + turtleneck	No	Too much upper-body coverage competes with facial focus; feels heavy.
Slip dress + sandals	Yes	Fluid lines balance bold accessories; elegant without clutter.
Linen shirt + wide-leg pants	Yes	Relaxed tailoring complements the ease of a soft updo and trendy shades.
Sequined top + leather skirt	Risky	High-glam elements may push the look toward costume if not toned down.

Tip: When in doubt, follow the \"one hero piece\" rule. Let your sunglasses be the standout element—keep jewelry minimal and clothing streamlined.

Step-by-Step: How to Style the Look Naturally

Follow this sequence to ensure your oversized sunglasses and updo come together cohesively:

1. Determine the occasion: Is this for brunch, travel, or a photoshoot? Casual settings call for softer execution.
2. Select your sunglasses: Choose a pair that enhances—not overwhelms—your face shape. Rectangular frames suit round faces; round frames flatter angular features.
3. Prep your hair with texture: Use a texturizing spray or sea salt mist before styling. This prevents the updo from looking too stiff or salon-perfect.
4. Create a low or mid-height updo: Avoid extreme height or tightness. Leave a few wispy strands near the ears and forehead to frame the face.
5. Position the sunglasses correctly: Ensure they sit flush on the bridge of your nose. If they slide, use non-marking silicone grips.
6. Check the mirror from multiple angles: Walk away and return to assess the full look. Does it feel authentic? Adjust looseness or accessories accordingly.
7. Add one complementary accessory: A delicate chain necklace or small hoop earrings can anchor the look without distraction.

This method ensures intentionality at every step, reducing the risk of appearing costumed or overly styled.

Real-Life Example: From Overdone to On Point

Consider Maya, a marketing professional attending a rooftop summer party. She wanted to make a statement with her new oversized tortoiseshell sunglasses and a sleek high ponytail. At first, she paired them with a sparkly halter top and chunky gold cuffs. In photos, she looked like a 1970s film star impersonator—striking, but not quite “her.”

She adjusted her approach: swapped the top for a black ribbed tank, traded the ponytail for a twisted low bun with face-framing pieces, and removed all bracelets. Suddenly, the sunglasses became part of a cohesive, modern look. Guests complimented her “effortless cool” rather than asking, “Are you dressed up for something?”

The transformation wasn’t about changing the core elements—it was about balancing them. By dialing back competing details, the sunglasses and updo could shine without dominating.

Dos and Don’ts: Quick Reference Checklist

To avoid the costume trap, follow this actionable checklist before stepping out:

Checklist: Styling Oversized Sunglasses with Updos
✅ Do choose an updo with soft texture or slight messiness
✅ Do wear neutral or monochrome clothing to balance visual weight
✅ Do ensure sunglasses fit properly and don’t slide down your nose
✅ Do consider your environment—urban streets favor subtlety over drama
❌ Don’t pair with other retro-inspired pieces (e.g., feather boas, vintage gloves)
❌ Don’t go for ultra-sleek, pin-straight updos unless professionally styled
❌ Don’t wear multiple statement accessories alongside the sunglasses
❌ Don’t forget to check reflections—sunglasses should cover eyes naturally, not comically

Frequently Asked Questions

Can I wear oversized sunglasses with a tight ballerina bun?

You can, but proceed with caution. A tight bun creates a very polished, almost theatrical base. To avoid looking costumed, add softness with curled tendrils around the face, wear matte-finish makeup, and pair with casual clothing like jeans and a tee. The contrast keeps the look grounded.

Are oversized sunglasses still in style in 2024?

Yes, but the styling has evolved. Current trends favor slightly smaller “oversized” frames—think just beyond the brow line, not covering half the face. Transparent arms, eco-acetate finishes, and soft geometric shapes are popular. The key is moderation: larger than average, but not cartoonish.

How do I stop my sunglasses from slipping when I wear them with an updo?

Updos pull hair back tightly, which can reduce grip behind the ears. Use silicone eyewear grips (invisible and removable), or lightly texturize the skin behind the ears with translucent powder to reduce slippage. Also, ensure the frame width matches your head—too wide, and they’ll slide no matter what.

Maintain Authenticity Through Intentional Styling

The danger of looking “costumed” comes not from wearing bold accessories, but from styling them without context. Oversized sunglasses and updos are powerful tools in personal expression—they’ve graced icons from Audrey Hepburn to Rihanna—but their power lies in how they’re integrated, not just displayed.

Authentic style respects proportion, environment, and individuality. It asks: *Does this feel like me?* Not *Do I look fashionable?* When you wear oversized sunglasses with an updo, let the combination reflect confidence, not imitation. Choose frames that suit your face, not just the trend. Pick hairstyles that match your lifestyle. Dress in pieces that resonate with your personal aesthetic.

As fashion continues to recycle and reinterpret vintage moments, the most timeless skill isn’t following trends—it’s adapting them with nuance. You don’t need to avoid retro influences; you need to own them with modern sensibility.

Final Thoughts: Own the Look, Don’t Wear It

Styling oversized sunglasses with an updo isn’t about replicating a magazine spread. It’s about curating a version of glamour that fits your life. Whether you’re walking through the city, lounging poolside, or heading to a weekend market, the combination can work—if it’s balanced, intentional, and true to you.

Don’t hide behind the sunglasses. Let them highlight your features, your mood, your moment. Pair them with a softly pinned updo, a linen shirt, and quiet confidence. That’s when the look stops being a costume and starts being a statement.

💬 What’s your go-to updo for wearing oversized sunglasses? Share your favorite combinations and tricks in the comments—let’s build a real-world guide shaped by lived style.