Does it matter what I wear to work? I like to be comfortable but occasionally catch a glimpse of myself in the lifts (I work in advertising) and think I look a hot mess. Will that hold me back?

The short answer to “Does it matter?” is yes and no. No one can be on point with their outfit every day. That’s why they invented uniforms. I tend to start the week in what I call “cosy clothes”, a tracksuit or a jumper. I probably look a “hot mess”, too, but it means I can be focused. The beginning of the week is when I do the school run, and don’t tend to arrange any meetings. So I’m happy to wear whatever I want.

When it gets to Wednesday and my son goes to his father’s for the latter part of the week, I start pulling out the outfits I love, and go to see people I need to make an impression on. It makes me feel good to switch it up and have glam days and chill days. When I like my look, I feel more confident about my meetings.

Advertising, I can imagine, is very image-based and of course you feel a certain pressure to look good. But do you feel a mess because you know you haven’t made an effort, or because you feel you ought to look good for your colleagues and clients? Neither is the “right” or “wrong” approach, but it’s always good to consider why you feel the way you do.

Only you can know whether your look is so lax that it will hold you back. We live in a selfie- and image-obsessed world: do you want to play that game, or do you want to do your job? Remember, there’s a risk that the more presentable you are, the more people want you around merely for decoration (not to mention how relentless the upkeep is).

Would looking smarter enhance your ability to do your job? Do what feels right for you, and what will help you achieve your goals at work. If that means putting in a bit more effort, then let’s face it: it’s probably worth it.

• Send your questions for Sharmadean to bossing.it@theguardian.com

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