Welcome to Level 5: Formal Wear – possibly the most fun but over-represented in our closets. I used to buy a new dress for every wedding or evening event I went to. I quickly amassed a collection of beautiful dresses that got worn once or twice before languishing for years and then eventually getting passed on.

Pretty dresses were also the first things I really focused my sewing energies on. Sewing dresses is fun! They’re so pretty! The fabric can be so pretty! But because I was so focused on making the pretty dresses of my fantasies, I didn’t actually sew dresses that I wore more than once. Or when I did wear them, I was shoe-horning them into an event that made no sense and I felt awkward. Maybe you’re that person who can massively over-dress and own it but I am really not.

I went through a phase in my twenties when all my friends either worked in the media or for charities. I got invited to A LOT of last-minute fancy events. With very few details on the mood or dress code. Like the time my now-husband invited me to a gala with his bosses with four-hours notice on a workday.

For a lot of this time, I was working as a substitute teacher and supplementing my income in retail. I was young, inexperienced and fairly poor. Going to these events was extremely intimidating and I learned quickly that my outfit greatly affected how able I was to hobnob with smart, successful and important people when I knew at the time I was not in their league.

When dressing for these events, I had a closet full of dresses, but it was so hard to gauge what was appropriate without an actual invitation. So many were too tight, short, or otherwise revealing for me to feel comfortable in front of my friends’ colleagues. Others were appropriate, but maybe cheap-looking or attention-grabbing when I wanted to look like I belonged.

As a result of all of these anxiety-inducing moments of choosing what to wear, I decided to pick a set of aspirational criteria to help me curate one perfect look to get me through all of the formal events of a season. Even if I don’t think I have something coming up, I make sure I’ve got an outfit at the ready, because who wants to turn down an eleventh-hour invitation with free dinner and maybe some dancing? My criteria won’t be the same as yours, but I suggest you think hard about the note you’re trying to hit to make you feel like your smartest, most elegant self.

My Level 5 Formal outfit must:

• Be comfortable. You won’t be able to focus on being charming and intelligent when talking to award-winning journalists if you’re focused on your dress riding up;
• Be appropriate. I always dress just one tick more conservatively than I think I need to for an occasion. More than once I’ve been in a situation where I thought my outfit was fine only to feel like my skirt was waaaay too short once I got there;
• Be unique from up-close, not across the room. I like my style to be understated. I like the idea of people remembering that I was well-dressed, but not necessarily what I was wearing. I want people to notice the details of my outfit after a while of talking to me, it right away;
• Feel like an elevated version of what I normally wear. There’s something to be said about taking a pattern you already wear constantly and making it up in a great fabric, texture or colour. You won’t feel like you’re trying to be someone else, just a fancier version of yourself;
• Feel safe. There are many shades of formal and the person inviting you might not be the most reliable at conveying the tone of a dress code. My Level 5 outfit is always something of a chameleon. It won’t look too much for cocktail attire but won’t be laughably casual for black-tie;
• Only take one risk. I only allow myself to try one new thing: a colour, a texture, a fabric, or a silhouette. I find if I do two things out of my comfort zone, I feel like an imposter. Same goes for hair and makeup. If my dress is special, I keep my beauty look basic. If I’m wearing a solid black dress, I’ll spend some time on my hair OR makeup. Not both. I like to look like I’m not trying too hard. Also, who has the time?
• Have an outerwear look. I hate seeing evening gowns ruined by covering them up with ski jackets. Get one classic, long coat that you will own for a decade. If you need to wear heels in the winter, at the very least walk in with nice boots on and put on your pumps at the coat check.

This might all seem like a ridiculous amount of thought (and pressure) to put into one outfit, but honestly, this strategy has saved me so many times. Instead of agonizing over what to wear, I get more time to brush up on the news before I head out, or sip a cocktail in my living room feeling fancy.