Developing a personal style that’s as unique and standout as you are is no easy feat, especially when attempting to convey your quirky and loveable personality traits to a new date. The good news is that having the confidence to play around with your sense of style will always make for your best look (and just to be sure, we asked Toronto stylist Sansyrae St. Martin to weigh in).

“As long as you feel good in what you are wearing, you’re dressing well,” she said. “How you feel reads much louder than any specific style.” To help break down what your outfit really reveals about your personality, St. Martin shares her expert style advice.

The look: Head-to-toe black (with shades of grey)
What it says about personality type: Bold, self-assured and always on the go
What to wear: We love the idea of a monochromatic uniform, too, with a wardrobe palette ranging from black to white and grey (and navy, for good measure). And you don’t necessarily need to break out of that comfort zone for just one night. “It’s really important to be comfortable with what you’re wearing – especially on a date – and to make sure that your clothes reflect who you are, she says. “I often wear shades of grey but try to ensure that the silhouettes are fun and flirty. A flouncy skirt or soft V-neck sweater can be just as flirty as colour.”

READ MORE: Spring 2015 runway looks to inspire your date night outfit

The look: The OTT style star
What it says about your personality type: “A woman who likes to be bold in her outfit is telling the world that she is happy to receive attention. For some, it may give a negative first impression but it will also attract like-minded people,” says St. Martin.
What to wear: “Colour definitely helps a woman stand out,” she assures. “But it’s not the only way.” This is good news for those of us who aren’t quite ready to step out in animal prints and Louboutins. “Accessories are a great way to add something playful to an outfit.” Try switching up your look with a coloured bag or belt for a sophisticated twist.

The look: You, just slightly vampier
What it says about your personality type: Your laidback, confident manner enables you to develop a uniform that’s all your own – and you just happen to be most comfortable in jeans and sneaks (so is Cara Delevingne, FYI). The trick is to step it up on date night without compromising your personal taste and comfort.
What to wear: “I encourage people to experiment with items that they can subtly take off: a scarf, handbag, coat, for example. By doing this, you can be daring and playful, but if you get nervous, it’s easy to remove the piece and feel like yourself again without anyone realizing what you are up to.” Sneaky.

READ MORE: 10 accessories to get you noticed on date night

The look: The trend watcher
What it says about your personality type: Like many of us, you look to the runways for inspo on what silhouettes to rock each season: The thing is, not all trends translate so easily on every body type. (Case in point: culottes can be horrendous on petite and curvy figures.) But that’s okay. “Style is so personal and needs to be a reflection of who you are,” says St. Martin.
What to wear: “Look at which celebrities you would want to be friends with, listen to what people have been saying about their personal style and if you are comfortable with people saying those things about you – then try to mimic their outfits,” she says. See how your favourite style stars dress for their body type. “If the look wouldn’t be flattering on you, it’s best to stay away.”

St. Martin’s guide to wearing colour on date night
“Bright colours, especially approaching spring, have the ability to make people happy, she says. “I love the idea of playing with colour because it can help portray a specific image.” To help, she’s compiled a handy legend on what your outfit choice says about your mood.

Red: confident, sexy, bold
Blue: Calm, cool, smart
Green: Sporty and fresh
Pink: Flirty, feminine
Yellow: Playful, happy, easygoing

READ MORE:
What to wear on a first Tinder date
How to go from the office to date night (for every type of outing)
10 accessories that will get you noticed on date night