Fashion dilemma candidate Kathryn has an upcoming family reunion where she'll be seeing style-forward cousins from New York and London for the first time in 15 years. She called on us to help her find the perfect outfit for her family meet-up in Montreal.

   Our Style Mission

Our mission is to break Kathryn out of her boring, all-black wardrobe and give her a sophisticated cocktail party look for an upcoming family event with some worldly relatives.

Our guest expert is Whitney Port, reality star turned fashionista and designer of her own line, Whitney Eve. She had these tips for us on dressing Kathryn:

• Kathryn would look great in a V-neck or sweetheart neckline, both of which are flattering on most body types. 

• A flowy skirt works well to camouflage and also looks feminine and sexy.

• Strappy sandals are fun for a cocktail look, and funky accessories to play it up.

   Our Look Book

We had a tough challenge trying to find a nice dress for Kathryn on a budget of $500. (We found lots in her size, but not in our price range!)

Our first attempt was a dress that didn’t quite fit Kathryn in the chest area (lucky busty lady!), which meant we had to run back to the shops and try again at the last minute. In the end, we came up with:

Outfit details

• Dark green layer detail Calvin Klein Dress: $80 at Winners
• Black onyx & wood bangle: $70 at Winners
• Black Eli Tahari leather clutch: $299 at Winners
• Black & metallic leather peep-toe heels: $90 at Aldo

Whitney Port’s opinion

• The dress is a nice colour, but a better colour could play up her blue eyes. It needs to be finished off on top with a cute bolero jacket, a pashmina wrap, or a sparkly cropped cardigan.

• A sweetheart neckline would have been better for her, and more substantial straps. Usually it’s best to stay away from horizontal lines, especially if you’re trying to camouflage an area.

• The bag is pretty cool, but it’s not the right look for this outfit. She should have a smaller clutch or something hands-free since she’ll be shaking hands and hugging a lot at her event. This larger bag would look great with jeans and a blazer, something more casual.

• I love the look of dark tights with a cocktail dress. The shoes are cute and unique and make her legs look great. The bracelet cuff is fantastic — the single statement accessory.

   Did our style picks make the “Do List” or “Don’t List”?

Kathryn loved everything. She felt the colour of the dress, a nice deep green, wasn’t something she would have picked for herself, but she definitely liked how it fit and looked. Plus, it was different than her usual grey or black. She also fell in love with the bag, even though we realized later it wasn’t quite right for this outfit.

Our style expert Whitney Port was super nice! She thought we did really well on Kathryn’s bottom half, but we could have picked a more delicate clutch purse. She also suggested different style tops, or alternatives to finished it off: e.g. a sophisticated crop jacket, shrug, or wrap.

   Tips we learned from our experts:

• It can be very empowering to push yourself toward wearing colour. Even if you’re scared, once you put it on you may be surprised by how it complements your skin tone. (Whitney Port)

• Solid black tights work with everything because they’re slimming, but don’t be afraid to play with texture.

• Watch your bag size for a cocktail party. It should fit your money (a small wallet), keys, a lipstick and a cell phone. That’s all you really need for an evening out.

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Please note: opinions expressed about fashion and beauty in this article are just that: our opinions. Feeling beautiful on the inside is what matters most, but we like to do what we can on the outside too.