“Do I want to play it safe?”

This is one of the most important questions to ask yourself when it comes to defining and developing your personal style. The problem is, the question of whether you want to play it safe often gets misinterpreted as a choice between being an individual, versus blending into the background with everyone else. Those are two different considerations, though – playing it safe doesn’t mean that your style choices have to be bland, boring, or predictable. Being an individual is not about dressing outlandishly. The true question is simply about deciding what level of risk you’re comfortable with, and creating a wardrobe that fits your character and disposition.

In short, there is no right or wrong answer for how far you should go with pushing the style envelope – the important thing is simply to be honest with yourself, and honor who you really are with style choices that match your personality. Here are some things to keep in mind when you’re making wardrobe edits to fit your individual tendencies and preferences.

If you are a natural risk-taker, you probably don’t need any encouragement for choosing clothes that are a bit bolder and more “out-there”, so when it comes to turning heads, you’ve got that one covered. Just make sure that you’re mindful about when to tone things down a little (a funeral is probably not the best place to debut your new red suit!), and use your intuition to make sure that you never cross the line from “bold” over to “ridiculous”. You want to stand out in a good way.

if you usually play it safe but want to take more risks, the key is to do it in baby steps. Nothing has to happen all at once; you can inch your way toward bolder choices over time if that’s what you want to do. Talk to a wardrobe consultant if you need some tips on how to spice your outfits up without doing too much too soon – accessories, small details in your garments, and the right shoes can make a big difference in how you look, without feeling overwhelmingly different. You can scale up gradually to bigger changes.

If you know you like to play it safe and are happy that way, don’t feel like you necessarily have to make bolder choices in order to look good. Sometimes less is indeed more, and often the most alluring outfits are ones that have a understated elegance. If a straightforward, classic look is your thing, roll with that and find little ways to make it your own, like playing around with color combinations and focusing on the best fabrics.

Remember, style is a very personal thing, and the most important factor is that you feel good about what you’re wearing. No matter what you choose, there’s a lot to be said for the confidence that comes with being comfortable in your clothes!

For those of you who are eager to start right now with stepping out and taking a chance on a new look, or if you want to but you just need a little push in that direction, here’s a pep talk to get the ball rolling!

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