Transitional Dressing Tips from Kendall, Kylie, and Hailey

Kendall, Kylie, and Hailey Offer Their Own Takes on Transitional Dressing

Transitional Dressing Tips from Kendall, Kylie, and Hailey

Transitional dressing can often feel like a daunting task. As the seasons shift, finding that perfect balance between comfort and style is essential. Emulating the effortless style of fashion icons like Kendall Jenner, Kylie Jenner, and Hailey Bieber can take your wardrobe to the next level. Let’s explore their top tips for mastering this art.

Layering is Key

One of the best ways to successfully transition your outfits is through layering. Not only does layering keep you warm during unpredictable weather, but it also adds depth to your look. Here are a few tips inspired by these trendsetters:
  • Start with a Base Layer: Choose a lightweight top or turtleneck which allows for additional layers without bulk.
  • Add a Mid-Layer: Consider a knitted jumper or cardigan that can be easily removed if temperatures rise.
  • Finish with an Outer Layer: A tailored coat or oversized jacket can elevate your look while providing the necessary warmth.


Kendall often opts for long cardigans paired with fitted tops, while Kylie prefers oversized denim jackets that add an effortless vibe. Hailey, on the other hand, favours chic trench coats to complete her outfits.

Mixing Textures

Mixing textures is another strategy that these celebrities utilise to enhance their transitional looks. The juxtaposition of different fabrics can create a visually appealing ensemble. Consider the following:
  • Combine Heavy with Light: Pair a chunky knit sweater with flowing silk trousers for a contrasting effect.
  • Incorporate Denim: A denim skirt with a soft cashmere top can offer the ideal blend of casual and chic.
  • Experiment with Leather: Adding leather to soft fabrics, like a leather skirt with a cotton blouse, can provide an edgy touch.


Kylie has been known to rock leather leggings with oversized knits, making it an enviable look. Hailey also loves mixing grunge-inspired elements with feminine fabrics, creating that perfect balance.

Accessorising Wisely

Accessories can make or break an outfit, especially during transitional seasons. They can provide functionality while elevating your overall look. Here are some tips:
  • Invest in Belts: A statement belt can define your waist and enhance layered outfits.
  • Opt for Scarves: Lightweight scarves can add a pop of colour and texture without too much warmth.
  • Choose Statement Footwear: Transitioning from boots to sneakers can offer versatility; pairing chic ankle boots with dresses can keep it stylish.


Kendall often sports bold jewellery to elevate simple outfits, while Hailey uses hats and berets to add a trendy twist. Meanwhile, Kylie embraces graphics and logos, particularly on her bags and shoes.

Play with Colours

As the seasons change, so do the colour palettes. Transitional dressing is all about adapting your colours to reflect the weather. Here’s how to incorporate colour effectively:
  • Use Earth Tones: Shades like olive green, rust, and beige are perfect for autumn, while soft pastels can transition into spring vibes.
  • Incorporate Neutrals: Neutrals offer versatility, allowing for the easy mixing and matching of pieces.
  • Pop of Colour: Add a bright accessory or statement piece to liven up an otherwise muted outfit.


Kendall often opts for neutral palettes, while Kylie loves vibrant hues that stand out. Hailey, conversely, favours monochromatic looks, sometimes adding a pop of colour with her footwear.

Focus on Fit

The way a piece fits can dramatically alter your overall look. Here are some pointers:
  • Tailoring is Essential: Well-fitted clothing helps to achieve a refined look, so don’t hesitate to take pieces to a tailor.
  • Balance Proportions: Pair fitted pieces with looser items to create a harmonious silhouette.
  • Don’t Sacrifice Comfort: Ensure that whatever you wear allows you to move freely, especially for daily activities.


Hailey is famous for her impeccable tailoring, opting for both structured and relaxed fits that complement her body shape. Kendall showcases tailored blazers that add sophistication, while Kylie often plays with oversized items that accentuate her style.

Adapt to the Occasion

Transitional dressing needs to be adaptable, ensuring you’re prepared for any situation that may arise. Consider these approaches:
  • Dress Up or Down: Skin-tight jeans can be dressed up with heels or kept casual with trainers.
  • Layer Smartly: Choose layers that can be removed or added based on the formality of an event.
  • Mix Dress Codes: Combine casual and formal elements, such as a casual blouse paired with a flowing skirt.


Kendall often transforms casual outfits into night-time attire with just a change of shoes, while Kylie loves to mix high-fashion pieces with everyday basics. Hailey makes layering look chic enough for any occasion, demonstrating how functionality can also be stylish.
In conclusion, mastering transitional dressing is all about experimenting, being adaptable, and taking inspiration from icons such as Kendall, Kylie, and Hailey. Their unique styles can offer guidance on how to navigate this transitional phase in fashion while remaining chic and comfortable. By layering strategically, experimenting with textures and colours, accessorising smartly, focusing on fit, and always being ready for any occasion, you can create a wardrobe that thrives throughout the seasons.