Medium-length hairstyles can be incredibly versatile and flattering, but some looks tend to cling to past trends, especially after turning 40.
Whether it’s the remnants of the 90s or early 2000s, these styles might make you feel like you’re living in a time capsule instead of embracing the present.
In this blog post, we will explore 16 specific medium-length hairstyles that may appear outdated and offer insights on how to modernize them.
With a fresh perspective and a few tweaks, you can transform these looks into chic, contemporary styles.
The Classic Farrah Flip

Once upon a time, the Farrah Flip was the epitome of glamour. With its voluminous layers and feathered ends, it was a statement. Today, it can feel more ‘retro’ than ‘radiant.’
The trick to updating this classic is to soften the layers and reduce the volume. Consider adding subtle curls with a straightener for a modern twist.
Embrace highlights that blend into your natural color to avoid the helmet-like appearance. A little sleekness can go a long way in bringing this style into the contemporary era.
The Rigid Blunt Cut

Rigid blunt cuts can sometimes project an image of severity. This style is characterized by its straight edges and uniform length, which can be both a blessing and a curse.
When too precise, it can appear unforgiving and draw attention to any slight imperfections. Balancing this with softer ends or gentle waves can mitigate that effect.
Additionally, introducing subtle layers or a side-swept fringe can bring a refreshing change, making it more adaptable and less ‘stuck in the past.’
The Permed Bob

Permed bobs evoke memories of the 80s, where perms reigned supreme. While they add texture, they can also appear dated if too tight and uniform.
To modernize, opt for looser waves that offer movement rather than rigidity. Consider balayage to add depth and dimension, breaking up the solid mass of curls.
Focus on moisture-rich products to keep curls hydrated and bouncy. This will keep the look fresh and lively, not crunchy and old-school.
The Stiff Layered Shag

The shag is a timeless style, but stiffness can make it feel like a relic. Layers are meant to give bounce and life, not to create a static look.
Add movement by incorporating texturizing spray or mousse. This not only lifts the layers but adds a youthful vibe.
Also, try reshaping the layers to frame the face more naturally for a softer appearance. This approach will reinvigorate a classic, making it feel fresh and current.
The Structured Inward Curl

Curls turned inward at the ends can sometimes resemble the style of decades past. This structured look can unnecessarily age the wearer.
To breathe new life into this style, consider loosening the curl with a larger barrel iron. Adding volume at the crown helps shift focus upward.
Highlighting the ends with a lighter shade can also provide a fresh contrast, modernizing the overall appearance.
The Helmet Head

When volume goes unchecked, the result can be a ‘helmet head’ look that feels more protective than pretty.
To deflate this style, focus on adding layers that reduce bulk. Using a round brush when blow-drying can help achieve a smoother, more streamlined appearance.
Incorporating shine serum can also enhance the sleekness, ensuring the hair reflects light and appears healthy, not heavy.
The Unyielding Pageboy

The pageboy cut is iconic, but its rigid structure can feel a little too defined. The heavy fringe and straight lines can appear harsh.
Soften the edges by adding a slight wave or curl. This will lend the look a more relaxed and contemporary feel.
Layering around the face can soften the entire silhouette, giving it a modern twist while maintaining its classic charm.
The Overly Feathered Layers

Feathered layers once symbolized style evolution, but too much feathering can feel like a blast from the past. The key is to balance softness and structure.
Opt for longer layers that flow naturally, avoiding the choppy, disconnected appearance. Incorporate styling cream to define layers without rigidity.
This approach maintains the style’s charm while making it adaptable to modern trends, ensuring it feels fresh and not frozen in time.
The Heavy Curtain Bangs

Curtain bangs can frame the face beautifully, but if too heavy, they can obscure features rather than enhance them.
Thinning the bangs or opting for a side-swept version can open up the face while maintaining that stylish edge.
Blending them into the rest of the hair with soft layers ensures a seamless transition, offering a graceful and up-to-date appearance.
The Overly Defined Layers

Overly defined layers can sometimes look too calculated. While distinct layers were once all the rage, they can now lack the natural flow desired in modern styles.
Introducing a mixture of lengths and tapering can break the monotony, providing a more effortless look.
Additionally, using a curling wand to add soft waves will create a cohesive, relaxed style that feels more grounded in today’s trends.
The Ultra-Slicked Back Look

The ultra-slicked back style can sometimes appear too severe, emphasizing the tightness and shine of the hair.
To soften this look, allow for some natural volume on top. A texturizing spray can offer that lift without deviating from the sleek aesthetic.
Blending the slicked sections with looser, face-framing pieces can transform it from stark to sophisticated, retaining elegance while reducing severity.
The Excessively Layered Bob

A bob can be a signature style, but excessive layers can make it feel chaotic. The plentiful layers, instead of being chic, might come off as cluttered.
By reducing the number of layers and opting for a more unified length, the bob can regain its timeless allure.
The addition of subtle highlights can also enhance depth, giving it a fresh and polished finish.
The Outdated Side Part

A strongly defined side part can sometimes feel overly traditional. While it brings structure, it might also restrict styling versatility.
Consider switching to a softer, more natural parting or even experimenting with a middle part to refresh the look.
This change can redefine the face’s balance and bring a contemporary vibe that feels both light and lively.
The Limp Lob

A long bob, or lob, is chic, but when it lacks volume, it can appear lifeless. The key is to inject some energy into the style.
Utilizing volumizing products and a blow-dry technique that lifts at the roots can revitalize it. Adding face-framing layers or a slight wave can introduce movement, ensuring it feels fresh and vibrant.
This approach combines the lob’s classic elegance with a modern twist, perfect for those seeking an update.
The Puffy Bouffant

The bouffant, once a symbol of elegance, can seem too extravagant today. Its height and puffiness may dominate rather than complement the wearer.
To modernize, reduce the volume and height, focusing on a sleeker silhouette. Use smoothing serums and gentle blow-drying to achieve a more streamlined look.
Incorporate a slight wave or curl at the ends for added texture, ensuring the style feels balanced and contemporary.
The Tired Outgrown Fringe

An outgrown fringe can often seem neglected, overshadowing an otherwise chic hairstyle. Its lack of shape can disrupt the overall harmony of the look.
Regular trims to maintain a neat fringe will prevent it from appearing messy. Alternatively, blending it into side layers can offer a softer transition.
This approach ensures the hairstyle remains polished and stylish, rather than feeling disheveled.