What to wear on a date: 7 Style Panel tips to make a good first impression

what to wear on a date
what to wear on a date

Knowing what to wear on your first date is no easy feat, especially with butterflies in your stomach. We all want to put our best foot forward (in a pair of sky-high heels!) when making that first impression, but let’s face it. The last thing you want is to sit in an uncomfortable dress at the movies or hobble around in new (painful) heels when your date decides to take a romantic walk at the end of the night. So how do you dress to impress and feel confident all at the same time? This week our Style Panel shares some of their best tips to score that perfect outfit for that perfect first date or 100th date.

If there is one thing the members of Style Panel can agree on, it’s to dress according to your date location and wear something you would feel confident and comfortable in. Both Kassandra Camponi of Kastles and Kira Paran of Northern Style Exposure are big believers in wearing your favourite pieces is the key to bringing confidence to the date. While Camponi loves to team her favourite dress with a pop of colour in the accessories department, Paran was all about dressing comfortably in her favourite pair of jeans. The Pretty SecretsSandy Joe Karpetz shows us how to prep us if the date takes you from a warm afternoon to a cool evening in the seamless transitional outfit. Still can’t decide on what to wear on a date? Jill Lansky of The August Diaries shares what not to wear just in case if you were thinking of taking out those harem pants out for the first time.

Question 105: What to wear on a date? Read the answers now! »


what to wear on a date kira

Kira Paran, 29
Edmonton | Northern Style Exposure

I honestly feel like everyone looks better when they feel comfortable and confident. So I wouldn’t try to be someone you are not; if you aren’t a heels person, it’s not the best idea to try to break in a pair of sky-high stilettos you can’t walk in. For me, dress for the location and activity. I think a movie date calls for your favourite jeans that fit you perfectly.

Kira’s wearing: Top, J.Crew. Jeans, Elizabeth and James. Hat, J.Crew. Sandals, Steve Madden. Bag, Alexander Wang.

what to wear on a date sandy

Sandy Joe Karpetz, 25
Edmonton | The Pretty Secrets

Depending on what your first date may entail, the classic floral sundress is usually a win. Pair it with a light denim jacket to easily transition from afternoon to early evening.

Sandy’s wearing: Dress, The Pretty Secrets Vintage. Sunglasses, The Row. Bag, vintage. Heels, Zara.

what to wear on a date christopher
Photography by Karis Drake

Christopher Wolf, 23
Halifax | Wolf Musings

Choosing an outfit for a first date depends of course on the type of date. Whatever your plans, you want to go with something that is comfortable and in your own personal style – be authentic and true to yourself – but maybe up the ante a little. My first date with my boyfriend was yoga, so I went with something a little more fashion-oriented :). I chose a look suited for a romantic dinner date.

I went with something that is figure-flattering and youthful, but still on the conservative side. You want to show you have personality and spunk, but also level of composure and refinery – dates can be boozy, but not floozy. Be comfortable, be yourself, but be classy while you knock ’em dead.

Christopher’s wearing: Blazer, gladiators and necklace, H&M Kids. Shirt, American Apparel. Pants, Bluenotes.

what to wear on a date jillian

Jill Lansky, 26
Vancouver | The August Diaries

My favourite date outfit is one of the simplest: jeans and a white tee. It’s comfortable and sexy in an unexpected way. Men like clothing they can understand, so keeping it simple and not necessarily trendy is a good way to get their attention in the right way (I would avoid harem pants, overalls, peplum, etc.). All that said, the most important thing in date wear is confidence. If you can wear a trendy item with class and confidence, it will get the job done correctly.

what to wear on a date kassandra

Kassandra Camponi, 26
Edmonton | Kastles

Being a married lady for sometime now, means I haven’t been on a first date in many moons. Now that doesn’t mean I don’t go out on dates with my husband. Whenever the hubby takes me out, I generally like to wear something that I feel cute in. I think the key to picking an outfit for a first date is finding something you feel confident in. This could be your favourite dress, pair of shoes, or a great pair of jeans. I believe that confidence is one of the most attractive things about a person. For my date look, I picked one of my favourite dresses with a few simple accessories & a little pop of colour with my purse. One other tip for a first date outfit is making sure you have a rough idea of what you will be doing on your first date so you aren’t inappropriately dressed. For example, I wouldn’t want to be wearing this outfit while bowling.

Kassandra’s wearing: Dress, ℅ Joe Fresh. Blazer, H&M. Heels, Kenneth Cole Reaction. Necklace, ℅ 424 Fifth. Purse, Target.

what to wear on a date becky

Becky Kung, 30
Calgary | Velvet & Vino

First dates are always tricky, so it’s a must that we feel our best in the outfit we’re wearing. My first tip is the importance of styling your look appropriately for the activities planned for the date. Try to get a feel of what the date looks like and dress to fit the mood. For instance, if the date involves going to a coffee shop or doing an activity, your outfit will look much more relaxed than going out for dinner.

I enjoy wearing a sexy shift dress for a dinner date. My preference is to keep my outfit simple, focusing on elegance and femininity with strappy heels and minimalistic jewellery. I love the balance in this dress being more conservative on the top and then more revealing at the bottom with a shorter length. This is my idea of a perfect dinner date outfit.

Becky’s wearing: Dress, Topshop. Clutch, Coach. Rings, H&M. Heels, Hudson’s Bay.

what to wear on a date kayla

Kayla Short, 26
Halifax | Short Presents

First dates can be stresssssssss-ful! But I don’t think your outfit needs to be. I would suggest striking a balance between wearing something that’s a little bit sexy, but still classy.

When it comes to making a good impression usually less is more; you don’t want all the bells and whistles distracting the person from getting to know the real you. Go easy on the makeup, the bold accessories, and hair and go for a relaxed (up-for-anything) look instead.

And for adding a little extra confidence I can think of none other than opting for a little leather jacket action. Honestly this bad boy goes with anything, and it’s a great way to add a little extra something to an otherwise basic outfit.

Kayla’s wearing: Jeans, Joe Fresh. Tank, Dynamite. Faux Leather Jacket, Winners. Heels, Aldo. Bag, Michael Kors.

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