Software CEO Shannon's wardrobe is full of grey, brown, and boring black. She's come to the A&K Headquarters to see if we can get her out of her style rut and into a day-to-night outfit that will work in the boardroom and on a date.

   Our Style Mission

Our challenge with software CEO Shannon is to remove the bored from her boardroom attire and give her a fun, flirty, feminine look that cantake her from day into night.

Our guest expert is Treana Peake, owner and creative director of Obakki Design House. She had these tips for us for styling Shannon:

• Shannon is in an industry that is predominantly male so she needs something that can command her respect. However, she can also wear things to help her embrace her femininity.

• Since she’s comfortable wearing a suit, she can wear something small and feminine underneath and then at night take off the blazer and she’s got a sexy, evening look.

• I think I would leave her in pants and a sexy top because that’s what it sounds like she’s most comfortable wearing.

   Our Look Book

We started out with a plan (a colourful dress, sexy shoes, accessories) and then strayed from it (ruffled skirt and some sort of top). At the last minute, we went back to the dress idea and had to return items we bought earlier in order to make it all happen.

Day Outfit details

• Luce silk sleeveless tunic dress in taupe: $89 at Scoop
• Bra: $34 at La Vie en Rose
• Black long sleeve slim-fit top: $27 at American Apparel
• Black opaque tights: $15 at London Drugs
• Black studded leather clutch: $25 at Plum
• Ted Baker “Kaydet” black knee-high fabric-leather boots: $192 at Lord’s Shoes

Night Outfit details

Same as above but:

• Remove the black long sleeve top
• Add necklaces (silver chains and glossy black beads): $10 each at Urban Planet.

Treana Peake’s opinion

• The clutch is really sweet. The jewelry is beautiful, it ties the dress together. The boots are nice, I like the boots.

• I saw her in colour in my head. I think it would give her a pop. She’s literally toe-to-wrist black (day), and the dress, to me, looks frumpy.

• Removing the shirt and showing some skin with the cowl arms is sexy and works for night. Maybe a tank or something else other than a long sleeve top would work better for day.

• It’s not really an easy look for transforming into night. She has to take the dress off, then the shirt off, and then put the dress back on. If you went with a blazer, it’s just one step to remove it and she’s ready for an evening date.

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

Shannon thought the outfit was fabulous. “They found a dress for me to wear that I wouldn’t normally, and I really liked it. I could put it with a suit jacket for the day and then wear it at night. The boots were fantastic. Fit perfectly, great height. And I can definitely wear this outfit on a date!”

Our style expert Treana Peake liked all of our accessories: the boots, the clutch, the neckalces. As for the main parts of the outfit, well, we’ve heard it before. Treana would have liked to see some colour, and a more flattering fit for her figure.

 

Tips we learned from our experts:

• Sling a pair of high heels in your bag and slip them on when you leave the office for an evening date.

• If you’re going out for an evening, show some skin. Arms or cleavage (choose one!)

• Invest in a great, versatile clutch that can help dress up your daytime outfit.

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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.