Lifestyle

What’s the best way to handle ‘Casual Fridays’?

It’s that dreaded time of year where our employer converts to casual-dress Fridays. I enjoy the security of just throwing on a suit and matching tie and not having to think about my wardrobe. Any tips for how to make a successful transition?

Oh please, get someone to dress you — because with such lack of confidence in your ability to go “business casual,” you are likely to end up looking like some store mannequin with an outfit that doesn’t match your personal style or generation. And Casual Friday isn’t a weekend barbecue, OK? If you wanted to be totally conservative and not deal with any fuss you could simply lose the tie on Fridays — just make sure the suit is killer and fits perfectly and that the shirt is crisp. If you want to be a little more adventurous, find a trusted female colleague who has a sense of style, and take her to a reputable men’s department store so that you start with a good eye and a good selection of appropriate attire from which to choose. Tell the salesperson what the agenda is, and you’ll have mix-and-match separates that will get you through the season safely.

I drive a taxi and I’m trying to save money to go back to college. Given the cost of using the cab for the shift and the gas, the amount of money I make in tips is critical. Do you think it’s OK for me to say to passengers that I am dependent on tips for saving enough money to go back to college, and that if I give them great service I hope they will reward me with a good tip?

I don’t think there is any harm in it, and depending on your approach you may engender sympathy and earn an incremental increase in tips. But it really depends on two things: how you come across, and whether you get me to my destination safely and in the route that makes sense so I don’t want to scream, “Why are you taking Fifth Avenue when you could have taken the Park Drive?” (Not that I’ve ever experienced that.) I think if you come across as earnest and likable, and not in any way that makes people feel obligated to tip you more than they would have, then I think you might see your income rise. Good luck.