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Inspired By Melania Trump’s Hat? Here’s How to Find a Flattering One at 60

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Dear Lauren, 

Melania Trump’s recent hat has me thinking about adding one to my wardrobe, but I’m worried about choosing the wrong style and looking frumpy. I’m 65 years old, how do I pick a hat that’s both fashionable and flattering? I’d love to hear your thoughts.

Barbara J. – Miami (US)

Dear Hat-Curious, Adding a hat to your wardrobe is a stylish way to update your look, and I love that you’re considering it! Taking style cues from public figures can be a great way to refresh your personal style and integrate new pieces into your wardrobe.

Hats aren’t just accessories—they’re statements that elevate an outfit. If you’re worried about looking frumpy, the issue may not be the hat itself but how it fits within your overall style. A well-chosen hat should feel like a seamless extension of your personality. This may be the perfect opportunity to explore styles that resonate with you and ensure your wardrobe reflects the confident, stylish person you are today.

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Finding the Right Hat

Instead of focusing on face shape rules, visit a local hat shop where you can try different styles and get expert guidance. Small hat shops often provide personalized service, helping you discover styles that complement your wardrobe and, most importantly, make you feel amazing. Many hat shop owners have a wealth of knowledge and stories, offering insights into the craftsmanship and history behind different styles.

Consider where you’ll wear your hat—will it be for work, casual outings, or special events? Defining its purpose helps narrow your selection. You may even find that one hat isn’t enough—different styles serve different occasions, and building a small collection ensures you always have the right piece to complement your wardrobe.

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For the best fit and a unique touch, consider a custom-made hat. Many small hat shops offer custom sizing, style adjustments, and expert insights that make a huge difference in how a hat looks and feels. A well-fitted hat doesn’t just sit on your head—it becomes part of your signature look. Investing in a quality piece means you’ll have a hat that enhances your wardrobe and lasts for years to come.

Wear It with Confidence

The key to wearing a hat? Confidence. If you feel unsure, you’ll look unsure. Wear it like you mean it, and it will feel effortless. Start with a style that speaks to you—a classic fedora, a playful beret, or a chic wide-brimmed hat—then build from there. If shopping online, choose retailers with good return policies so you can experiment without commitment.

A great hat isn’t just about fashion—it’s about how it makes you feel. If it seems out of place in your wardrobe, maybe it’s time to refresh your style as a whole. Let your look evolve, and let your hat be a reflection of the fearless, fashionable woman you are.

Be Fearless. Stay Fashionable. Have Fun!

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About The Author

Lauren Simmonds | The Fearless Fashionista

Lauren Simmonds | The Fearless Fashionista

Lauren Simmonds is a Style Coach, Founder and Chief Fashion Officer of The Fearless Fashionista and author of “Find Your Fabulous: The Fearless Fashionista® Approach to Developing and Owning Your Style“. She conducts style workshops, as well as provides personalized style consultations. Her motto? “EVERY woman can do something to improve how she shows up in the world”.

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