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When is the Right Time to Hire a Personal Stylist for Men?

Writer's picture: Jacqueline LoganathanJacqueline Loganathan

If you’re wondering whether it’s the right time to hire a personal stylist, you’re not alone. Many of my clients tell me they’ve been considering it for a while, and the reasons they finally pull the trigger are surprisingly similar.


Whether it’s about elevating your style for a major life change or simply gaining confidence in your clothing choices, a personal stylist can make a big difference. Here are seven common scenarios where hiring a stylist can be a game-changer:


  1. Starting a New Job


    Transitioning into a new role is the perfect time to take stock of your wardrobe. Maybe you’ve been in the same job for years and realize your outfits have become stale, or you’re moving from working at home to a role that requires more than a t-shirt and jeans. Giving your wardrobe the refresh it deserves can help you:


    • Get that extra boost of confidence as you venture into this new life stage

    • Save time by sourcing quality pieces that fit well and last

    • Create a wardrobe that aligns with your new role and company culture


  1. Preparing for a Vacation


    I don’t know about you, but before a vacation, I’m always scrambling to “just pick up one more thing.” Unless you’re planning a shopping spree in Paris (and even if you are), it’s natural to want to pack your best to look your best on vacation. Hiring a stylist can:


    • Ensure you look and feel your best for every activity, from beach days to formal dinners

    • Help you pick out obscure items for themed nights or special outings

    • Help you pack efficiently with versatile, destination-appropriate outfits


  2. Navigating a New Relationship Status


    Big changes in your personal life, like a divorce or getting back into dating, are excellent opportunities to refresh your look. Many of my clients going through a personal life change gift themselves a stylist for a confidence boost. A stylist can:


    • Help you rediscover your personal style and build confidence

    • Guide you in choosing outfits that suit your personality and body type

    • Make shopping stress-free and save you time



  1. Preparing for a Holiday or Major Event


    Whether it’s a wedding, a public appearance, or an office holiday party, events come with the opportunity to dress to impress. And good news: you don’t have to buy everything new. A stylist can:


    • Help you create standout outfits for various occasions

    • Find pieces that balance festive and functional

    • Take the stress out of last-minute shopping


  1. Transitioning Into a New Season


    Especially in climates with four distinct seasons, the changing weather is a natural time to reassess your wardrobe. A good rule of thumb: if you haven’t worn it in over two years, it’s time to toss or donate. A stylist can:


    • Recommend pieces that keep you comfortable and stylish in the new weather

    • Help you incorporate trends without losing your personal style

    • Build a wardrobe that's functional and fashionable year-round


  1. Entering a New Phase of Life


    Life changes, like turning 40, becoming a parent, or stepping into retirement, are often cues to refresh your wardrobe. You may still fit and feel comfortable in pieces you’ve owned for years, but without realizing it, you’ve likely outgrown the style. A stylist can help you:


    • Redefine your style to match your new lifestyle

    • Simplify your wardrobe while elevating its quality

    • Make dressing well a seamless part of your daily routine


  1. Experiencing a Weight Change


    We all have clothes we love but no longer fit. It’s easy to hold onto them, thinking we’ll eventually gain or lose the weight to wear them again. And maybe we will… but in the meantime, there’s no reason not to get a few new pieces that fit and make you feel great now. A stylist can:


    • Help you rebuild a wardrobe that flatters your current body type

    • Recommend brands that fit well and boost your confidence

    • Guide you in choosing versatile items, colours, and patterns that work as your body changes


There’s no perfect time to hire a personal stylist, and there’s no rush either. As the term suggests, hiring a stylist is deeply personal. Take your time, do you research, and reach out to me when you’re ready.



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