How to Stop Dressing Too Safe & Embrace Your Style

As we get older, it’s common to worry about dressing ‘too young,’ but in reality, that fear can lead to playing it too safe and avoid current fashions. If you’ve ever wondered how to stop dressing too safe while still feeling like you’re not going to look like you’re too young (or feeling ridiculous), you’re not alone. The challenge is stepping outside your comfort zone without feeling foolish or making costly mistakes that make you feel more guilt about wasting money again.

The Fear of Fashion: Why We Play It Safe

Many women over 40 hesitate to explore contemporary fashion choices because they don’t want to appear like they’re trying too hard. Ironically, this fear often drives them straight into uninspiring, outdated clothing options that don’t reflect their vibrant personalities. The truth is, if you’re worried about dressing too young, it’s doubtful that you will. Your self-awareness will naturally guide you toward styles that feel appropriate for you, though you may end up too safe and boring because of your unfounded fear.

embrace contemporary trends that speak to you - from crochet to metallics and statement accessories

Which are the current trends that you love that speak to your style? Here I’ve embraced crochet, metallic garment and a statement necklace

Embracing Your Style in a Way That Feels Right for You

You can stand out and feel stylish and this doesn’t mean dressing in loud prints or trendy cuts that don’t resonate with you. Instead, it’s about understanding what your style looks like for you. Here’s how to explore it in a way that feels authentic:

Start Small: Instead of overhauling your wardrobe overnight, introduce small elements from current fashion trends. Try a statement necklace, a coloured (rather than black) handbag, or an eye-catching scarf in your signature colours.
Experiment with Colour: If you tend to wear neutrals (or just head to toe black), try adding a single piece in a colour that brings out your eyes (repeating your eye colour is always a winner). Got brown eyes and think “that’s just another neutral” peer into them and then notice what kind of brown they are – some have an orange element, others red, some burgundy – find the colour in your brown eyes and really make them pop by wearing that coloured version of your brown in your top. So many women are scared of colours because they don’t know which ones make them look great – this is just one of the benefits of a personal colour analysis (get yours here).
Find Your Patterns: Patterns can be a great way to add personality to your wardrobe, but they need to feel like you. Florals, geometric prints, and abstract designs all give off different vibes—find what aligns with your style. Pattern choices very much relate to both your physicality, such as your hair and skin, if you’ve got straight hair maybe a stripe is your best pattern. Alternatively, if you have curly hair, try curved prints, from florals or polka dots to abstracts. Got freckles? Try leopard prints or florals (whichever floats your boat) as they create harmony with your skin.
Assess What Feels Right: The key to long-term success is reflection. Take note of what makes you feel confident and what doesn’t. Over time, you’ll refine your style and become more comfortable with making choices from the lastest fashion trends.

Why Your Wardrobe Should Reflect Your Confidence

One common mistake when learning how to stop dressing too safe is buying pieces that feel different but aren’t actually right for you. Instead of random purchases, take time to understand what styles align with your personality while still pushing you beyond your comfort zone. Instead of shopping impulsively:

Understand Your Personal Style: Before making changes, take stock of what you truly love and feel comfortable in.
Try a Style Challenge: My Evolve Your Style program is designed to help you gradually experiment with new looks in a structured way, so you don’t feel overwhelmed. Over 31 days, you’ll try small changes that lead to a more confident, authentic style.
Ease into Change: If you’re used to wearing understated outfits, suddenly switching to dramatic, edgy pieces can feel unnatural. Instead, make gradual shifts—like wearing a bolder necklace before trying a statement jacket.
Take a Photo: Taking outfit photos can also be a helpful exercise. When you see yourself in different outfits over time, patterns will emerge. You’ll notice what makes you feel stylish and confident versus what feels forced or uncomfortable.

Embrace a colour that you love with modern styling and garments

Comfort Doesn’t Have to Mean Frumpy

As we age, comfort becomes a priority—and rightfully so! But comfort doesn’t have to mean loose, baggy, or unflattering. Thanks to modern fabrics with stretch and structure, you can have both comfort and style.

Prioritize Fit: Well-fitting clothing instantly elevates your look. Tailoring or finding brands that cater to your body shape makes a world of difference.
Look for Elevated Comfort Pieces: Soft fabrics, structured stretch materials, and well-cut designs can keep you comfortable while looking polished.
Balance Relaxed & Refined: If you love flowy pieces, balance them with something structured—like pairing a soft, draped top with tailored pants.

Your Wardrobe Should Support the Life You Want

Style isn’t about following trends slavishly —it’s about expressing who you are and feeling your best. If your wardrobe isn’t serving you, it’s time for a refresh. Instead of settling for “safe” clothes, think about what you want from your style in the next year. Who do you want to be? What do you want your clothing to communicate? How can your wardrobe support your life goals? Yes, that’s a question I always consider with my clients when I’m doing a style consultation. So many women will say “no” to invitations and opportunities as they don’t feel like they have the right thing to wear. Let’s make sure your wardrobe supports you and enhances your life rather than letting it hold you back.

If you’ve been holding back, now is the perfect time to learn how to stop dressing too safe. Stepping into authentic style doesn’t mean being flashy—it means dressing in a way that truly represents who you are and where you’re headed. If you’re ready to step out of your comfort zone in a way that feels empowering—not scary—Evolve Your Style is here to guide you. Evolve Your Style is a 31-day style challenge designed to help you step into a more confident style—one small step at a time. Each day, you’ll try something slightly new, giving you space to experiment and refine what works for you.

By the end of the challenge, you’ll have a clear understanding of what you love, what suits you, and how to dress in a way that feels contemporary yet effortless. Let’s make 2025 the year you dress with confidence, comfort and authenticity.