Pop Quiz: What’s the Right Thing to Wear for Which Holiday Event?

Credits: Photo - Anonymous, Styling - Sarah G. Schmidt, Location - Sarah G. Schmidt's home


Have you ever done one of those quizzes where they describe a scenario and you are to select the best fit from a selection below? Some may call them “Multiple choice questionairres” but I like to refer to the as my own kryptonite. For whatever reason I find a way in my mind to make each plausible via hmm-ing and haw-ing thus defeating the purpose of process of elimination. Le sigh.

Lululemon’s retail store garment bags tell me to, “Do one thing a day that scares you.” Touché, Lululemon, let’s face a fear. For instance, I could wear Croc shoes. That’s terrifying but a hard pass for me. A gal needs her morals and it’s off topic. I need to meet this particular fear head on. Thus, I’ve created my own multiple-choice style pop quiz. Here’s a few holiday season scenarios where what you wear matters.

Situation 1: (Fellas) You can’t wait for tonight as there is going to be so much food and your favourite people. This year, you decide to swap out your usual ugly Christmas sweater for a graphic holiday word play pun silk screened onto a crew neck sweatshirt instead. You’re headed to a…

  1. Friends Party
  2. Work Party
  3. Family Meal
  4. NYE Party

Friends Party! Yes, put on that fresh, silly sweater and pair with a pair or dark jeans or chinos. You’re about to let loose with your closest people so showing up to your bro and his partner’s new place is a bit more casual in dress is totally appropriate. 

Situation 2: (Ladies) Wearing something that is tidy, yet comfortable is key. You choose a button down shirt and knit palazzo crop pants over tights. The palazzo’s have a stretch waistband that sits at the small of your waist so you can sit easily. You’re going to a….

  1. Friends Party
  2. Work Party
  3. Family Meal
  4. NYE Party

Family meal! Yes, looking nice for family stuff is still important. But so, too, is being able to eat. Wear something that is simple yet polished and you’ll be enjoying seconds (and thirds) quicker than you can say, “pass the eggnog.”

Situation 3: (Fellas) You hit the hotel lobby wearing you favourite navy suit. But tonight you’ve swapped the matching jacket for a black velvet dinner jacket. You’re felling might Bond-esq in this dapper A.F. thing. You’re going to a….

  1. Friends Party
  2. Work Party
  3. Family Meal
  4. NYE Party

Work party! Yes, it’s a party but that does not mean you can let your guard down. John from accounting will still be there. It’s a work party, so unless you work at an ultra causal place, now is the time to suit up.

Situation 4: (Ladies) You’ve been dying to wear your thin strapped, dark velvet slip dress that hits above the knee since you got it two months ago. But you can’t just wear this little stunner any place. Nope, you’ve saved it for one of the sexiest nights of the year. It’s a big night and you’re feeling yourself.

  1. Friends Party
  2. Work Party
  3. Family Meal
  4. NYE Party

NYE Party! If you’re headed for a night on the town, get gussied up in a special dress. You’re not with your family or coworkers so feel free to show some skin if you so wish. Don’t forget the sparkly “2017” glasses or tiny sparkly top hat.

Oh, holiday dressing is just so fun. Different situations call for different attire. Making sure you stand out for the right reason is crucial for advanced personal style. Be safe, wear a warm jacket, and have fun this season.