Thinking about buying a Christmas gift for your boss? Not sure what to give your child's teacher? What about a gift for your landlord?

Plenty of us are facing these tricky questions as we try to pick affordable-but-considerate gifts to show appreciation for the not-as-special people in our lives.

Who doesn't wonder if a box of chocolates is suitable, or if it comes off as being cheap? Is it appropriate to give a bottle of booze to your child's teacher? How much do you tip the paperboy? Is it appropriate to re-gift?

As with anything, there is gift-giving etiquette and rules to follow.

Most experts agree, the rule of thumb is to use common sense and base the gift on the type of relationship you have with the person, be it a boss, co-worker or landlord, and how close you are to the person. If you don't feel comfortable giving a certain gift, don't do it.

Be aware of cultural or religious taboos, don't go overboard on a gag gift, and consider including a personal note with the gift, experts say.

Is re-gifting a no-no?

When it comes to re-gifting unwanted gifts, tread carefully. The biggest risk is the recipient or initial gift-giver, if kept in the dark, may figure out the re-gifting ruse.

Melanie almost learned the hard way when she re-gifted a pair of earrings given to her by her longtime boyfriend's mother.

Melanie appreciated the thought, but let's just say the earrings weren't her style.

"They were hideous," said Melanie, who asked CP24.com to withhold her last name, for the obvious reasons. "Not to be rude, but they were meant for older women."

Instead of putting on the earrings with a brave face, Melanie gave them to her mother. She said her heart almost jumped out of her chest at a housewarming party, where her mother wore the earrings without her boyfriend mother noticing.

"My boyfriend's mom hasn't figured it out and, hopefully, she won't," Melanie said.

Re-gifting depends on the feelings of the giver, but it tends to be acceptable when there's no risk involved – basically, in a situation where there's no chance the recipient will find out it's a re-gifted item and have their feelings hurt.

Avoid giving a dreadful gift

Giving a dreadful gift is one way to leave someone feeling let down. Etiquette experts at Toronto's The Etiquette Advantage suggest people to avoid the following gifts:

  • Something that is inappropriate (sexual or political, for example)
  • Something that has been used
  • Something that is overly expensive and will leave the recipient feeling uncomfortable
  • Personal hygiene items ("Am I supposed to take a hint?")
  • Miscellaneous clothing (giving a shirt and tie that don't match, for example)

In cases where the acquaintance isn't personal, a box of premium chocolates (if the person isn't watching his or her weight), a gift card to a restaurant or a bottle of wine are appropriate, experts say.

For a boss, make sure gift-giving for superiors is common or acceptable at your workplace, because you may run the risk of looking like a suck-up.

Aside from wine, a food basket or homemade cookies are frequent options.

A bottle of alcohol is a typical "go-to" gift people turn to when they don't know what else to give. If you're giving wine to a boss, colleague or client, make sure they drink wine and, if so, try to find out what type they enjoy to be sure it will be well-received.

Whether it's appropriate to give wine to your child's teacher, for example, largely depends on your child, your relationship with the teacher and the bottle of wine you choose, according to Winefox.ca, an informative website for wine drinkers.

Teachers appreciate getting supplies for the classroom, according to The Etiquette Advantage.

If you're attending a party, bring a bottle of wine the hosts can enjoy anytime.

To tip or not to tip?

There are also rules when it comes to tipping the people you've been dealing with all year – the people who cut your hair, babysit your kids, deliver your newspaper and walk your dog while you're at work.

There are no hard rules because the decision is so subjective, but consider the quality of the relationship, according to The Etiquette Advantage.

If the person came through during an emergency or treats you well and is reliable, you will want to be more generous.

The Etiquette Advantage offers these tipping guidelines, depending on the type of service:

  • Nanny: Tip about one week's pay or give a personal gift
  • Babysitter: Give half of a typical evening's total pay
  • Barbers and beauty salon: Tip half of the whole amount of one haircut, or give a bottle of wine
  • Dog walker: Give half to the whole cost of a week's service
  • Newspaper carrier: Give $10 to $30
  • Housekeeper: Give half of one day's pay, plus a gift if you have a close relationship
  • Apartment superintendent: A tip of $25 to $100, depending on the relationship

When it comes to tipping, The Etiquette Advantage offers these words to live by: it's great to be generous, but our pockets aren't deep enough to tip everyone who is kind to us.