Valentine’s Day: 10 Style Panel Tips for What to Wear, Date or No Date

Date February 10, 2017

Valentine’s Day is not everyone’s cup of tea. It’s a holiday to celebrate love, but some may ask: why do we need a holiday to tell us? Let’s be realistic, sometimes we just need an organized day to remind us to show and share our love and thanks with those closest to us. Valentine’s Day is a carefree one, so why not dive in and have fun.

So, what to wear on Valentine’s Day? We usually think of a few options: feminine, flirty and plenty of red and pink. Paging Rihanna at the Grammys? Maybe. But for tips on how to break that down for a date or a night out with the girls, we asked our experts in residence, the Style Panel.

Miss Melissa’s Melissa Knight loves dressing girly, but hardened her short red dress with studded overcoat for an added unexpected touch. Stephanie Sterjovski went for the tricky pink and red look, which we daresay she pulled off with flying colours (no pun intended). Kassandra Camponi of Kastles went fairly literal, and chose to wear hearts from head-to-toe. So, without further ado, let’s help you find out what to wear on Valentine’s Day.

Question 38: What is your favourite way to dress for Valentine’s Day? Read the answers now! »

Valentines Day Stephanie Sterjovski — Photography by Anna Tsoulogiannis

Stephanie Sterjovski, 22
Toronto | Stephanie Sterjovski

I’ll use any excuse to dress up, even if it is for the made up holiday (Valentine’s Day). I’m still a huge fan of colour blocking, especially when it comes in the form of pink & red. I added my own touch with a sparkly statement necklace and skinny leopard belt, and then toned everything else down with nude pumps.

Stephanie’s wearing: Top, J. Crew. Pants, H&M. Belt, J. Crew. Necklace, J.Crew. Shoes, Steve Madden.

Melissa Knight, 30
Vancouver | Miss Melissa

I’ve never been a huge fan of Valentine’s Day which is funny because I am a huge fan of dressing girly and an even bigger fan of chocolate. You’d think I’d jump all over a day that allows me to get dressed up and eat as much heart shaped chocolate as I please. I don’t have any plans yet for the 14th but I think the romantic look of this vintage dress mixed with the edginess of this studded sleeved coat perfectly represents my love/hate feelings towards Valentine’s day and will be a very appropriate look for me on that day.

Melissa’s wearing: Coat, Zara. Dress, Vintage. Pumps, Aldo. Satchel, Coach.

Christina Cravero, 27
Toronto | The Style Mogul

Valentine’s Day is such a romantic fun flirty day, whether you spend it with your closet friends, family, your beau or hubby, this is a day you should always feel loved! To me Valentine’s Day always needs a super girly outfit, which is why a fun dress and a sequin blazer is the best way to celebrate the day of love!

Christina’s wearing: Dress, Danier. Jacket, Zara. Wedges, Zara. Bag, Danier. Shoe clips, Nine West. Necklace, c/o Live Love Shop. Bracelet, c/o Persona. Watch, Michael Kors. Sunglasses, Pucci.

Melanie Morais, 24
Edson, AB| BornLippy

I love an excuse to dress festive and Valentine’s is definitely one of those days. I usually go for the typical red and pinks but I thought this year I’d try out some different colours while still showcasing my heart(s) on my sleeve or ahem..shirt! You can definitely have some fun experimenting with outfits this day, and I love mixing the heart print with my polka dot belt! It’s fun yet casual which is what I love. When it comes to plans, the boyfriend and I will be very low key and probably go out for dinner and come home and enjoy the red velvet cupcakes I baked! We will have our “Valentine’s” the next weekend in beautiful Jasper! Have an amazing Valentine’s Day!

Melanie’s wearing: Blouse & Belt, Gap. Trousers, H&M. Watch, Michael Kors.

Vickie Laliotis, 28
Edmonton | Adventures in Fashion

If you’re anything like me, the idea of Valentine’s Day conjures up images of candy colours, heart motifs and everything in between. So when dressing for the day, I like to take elements associated with the holiday—the colour red, for instance—and incorporate them with edgier pieces for a more grounded, sophisticated look. In this case, I opted for a vibrant red jean with loads of leather and stud detailing, throwing in a flirty peplum for some added oomph. It’s an easy, understated approach to the holiday, and as an added bonus, this look is appropriate for day or night… You can’t go wrong!

Vickie’s wearing: Leather jacket, Zara. Top & necklace, Urban Outfitters. Jeans, Joe Fresh. Booties, Aldo. Clutch, Michael Kors.

Valentines Day Barbara Ann Solomon — Photography by Trevor Negin

Barbara Ann Solomon, 25
Toronto | Barbara Ann’s Style Blog

There is nothing greater than being in love and I feel fortunate that my photographer is also the love of my life. On Valentine’s Day my boyfriend and I are planning a date at a local Thai restaurant and then a weekend getaway up north with another couple. During holidays, like Valentine’s Day, I like to dress to reflect the day. This tank, part of the LOVE ME collection by Curtis Kulig, contrasts well against a bubblegum-pink form-fitting peplum skirt. I added a silk robe and a blazer to tone down this bold look for the office, but kept it fun with my layers of necklaces. There are a limited number of ways/days to wear bright reds and pinks together, so when given the opportunity on Valentine’s Day, I’ll usually be up for the challenge and hope to not look too much like a walking greeting card.

Barbara Ann’s wearing: Blazer, T. Babaton. Robe, Wilfred. Tank, Love Me by Curtis Kulig. Skirt, Topshop. Tights, H&M. Heels, Max Studio.

Kassandra Camponi, 26
Edmonton | Kastles

Valentine’s Day seems to be one of the most feminine holidays around, so naturally I embrace it. I will be rocking a lot of pink, reds and anything feminine this week. That’s right I will basically be a giant Valentine’s Day card walking around. As for my plans for Thursday, the hubby and I will be hanging out with friends & then we will celebrate together on the weekend. We take turns planning fun Valentine’s Day dates, this year it is my better half’s turn to do the planning. Oh and whatever we end up doing you can bet I will be some variation of pink & red. Happy Valentine’s Day!

Kassandra’s wearing: Top, Anthropologie. Jacket, Old Navy. Skirt, Jason Wu for Target. Necklaces, Joe Fresh. Heels, Vintage. Shoe Clips, DIY.

Stephanie Koch, 27
Kelowna | Inherited Jeans

I like to view Valentine’s Day as a time to celebrate all relationships that you value in your life, not just romantic ones. This way, no matter what your romantic situation, you can look on the day with joy and appreciation for all the beautiful people in your life. I remember one year in my teenage-dom when I was thinking I was too cool for my parents, my dad asked if he could reserve me for Valentine’s Day. We went for pizza and to a local arcade and played games all evening. It ended up being just what we needed to reconnect. This year I am flying to Vancouver to visit with my family and I couldn’t be more excited! This outfit isn’t particularly sexy, but it’s fun and festive; just how I like to keep Valentine’s!

Kayla Short, 26
Halifax | Short Presents

I don’t necessarily get wrapped up in the elaborate hype of Valentine’s Day, as I feel it is a slightly commercial holiday, and I think we should show our love and affections to the people we care about all year round. I will however, take any excuse to get dolled up and eat a deliciously rich meal.

For Valentine’s Day dressing I like to keep the style flirty, and the hair and make up slightly romantic. This red lace peplum seems to fit the bill perfectly; this ruffle detailing is so utterly feminine as it hugs into the body just so. From the front, the peplum looks quite simple: red fabric with a textured lace overlay, but it’s the ultra sheer back that allows for a slightly more scandalous statement. With a fresh face, and some soft curls I think this outfit will be perfect for an evening out indulging in some of Halifax’s finest dinner cuisine.

Kayla is wearing: Peplum, Dynamite. Necklace, c/o Ell and Em. Cigarette Pants, Suzy Shier. Booties, Vince Camuto. Bracelet, Short Presents The Etsy Shoppe.

Cara McLeay, 28
Vancouver | A Fashion Love Affair

I like to dress up for Valentine’s, but don’t necessarily want to go all pink and red when heading out on the town. This year I am going to dinner and a comedy show, so I am pairing a girly dress with a tough leather jacket to make a fun look that doesn’t look too over the top.

Cara’s wearing: Dress, Jack by BB Dakota. Leather jacket, Muubaa. Pumps, Bebe. Clutch, Banana Republic. Necklace, Albeit.