Helping A Shy Friend Reinvent Their Style

Those who are a little more nervous or shy than most will understand what it’s like to be modest, to be happy in the background, and to try not to cause any undue drama. In some ways, these qualities are laudable and worthwhile, because it’s easy to appreciate those who aren’t so in love with themselves they have to center who they are in every situation and conversation.

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That said, residing in your shell as a default is not always a healthy way to live life. If we have friends like this, it can be nice to inspire confidence in them, to encourage them to speak their minds and express themselves freely, and to make time and give them the space to do so.


If you’ve noticed that a friend seems to be more involved in fashion, or you have an event coming up, you might help them step out of their comfort zone and begin dressing for their personal well-being. But to what degree should we help, and to what degree should we let them explore alone, trusting their judgment?

In this post, we’ll discuss how to help a shy or nervous friend reinvent their style for the better. Without further ado, let’s get started:

Helping To Clean Or Reorganize Their Wardrobe

It’s always helpful to begin the process from the very basics, such as by assisting with the cleaning or reorganization of their wardrobe. Perhaps it’s been years since they had a real clear out, or they just want your opinion to manage some of their spare items.

Here you can sort out their garments over a weekend and perhaps ask them to try on every piece, so you can easily identify what fits and what doesn’t. If they don’t mind losing some of the non-fitting items, you can place them into a few categories - like those for sale, those to donate, and those to hand down to other family members.

Some of these items might be dry-cleaned to restore their natural condition, others may require repairs, and some may be worth recycling. When the current stock of items has been properly “filtered,” you now have a few styles and outfits to work from should you make new style additions.

Considering Their Natural Style & Tastes

Helping a friend with their style is hardly about telling them what to wear and how to wear it, of course, rather it’s more about helping them understand what styles and tastes they like.

In some cases, they might not have a developed style, and that’s totally fine, too. It’s not as if you need to fit particular character interpretations to dress well or fit into a clique, you just need to be you.

So, if they prefer wearing cardigans and more comfortable clothes during seasonal wear, you may measure them and opt for items that fit them, or head to a local tailor and have items fitted so they don’t look shabby. You can also help with certain measures like finding glasses that fit their face shape or heading to your stylist or salon to perfect both of your hairstyles, going through a fun change together and taking it lightly.

Building Outfits Or Event-Specific Dress

It’s hard to build a full style for a friend who may enjoy wearing anything that works, and there’s no issue with that either.

It’s much easier and healthier to build an outfit for specific purposes, like one for their first date, or perhaps an upcoming college prom. This way you can visit your favorite designer or retailer of prom dresses and find a beautiful style that helps them feel the most confident.

Perhaps you’re attending an event together and can theme your dress around that, this way they’ll be able to see the logic you use when putting an outfit together and how you make your decisions. That in itself can give them more confidence in understanding what they like, and how to go about it.

Heading To Events

Heading out into the world with a new style can feel a little nerve-wracking at first, because you’re not sure how it will go down. That’s why heading to the event with them can be so healthy, because through this lens you’re showing them that actually, how an outfit makes you feel is so much more important than trying to find the approval of others, and even then, most others won’t laser-beam onto your dress and judge you for it anyway.

With this advice, you’ll have helped a shy or unsure friend reinvent their style and do so with a sense of autonomy and confidence. We can only hope to find a friend like you!

This is a collaborative post. I am so grateful to all who contribute to Glitz and Glam By Tiff.