Ask A Stylist

by Shai Thompson

It can be difficult to feel amazing every day, but I’m here to help you find answers and give direction when it comes to creating and organizing your wardrobe. Always remember: nobody’s perfect! Email your questions to

Q: I am going on a date for the first time in 30 years. I am a fit 63-year-old woman and we are fine dining. What do I wear?

Congratulations on getting back into the dating world! And thank you for sharing your age, as dressing appropriately for any age is important. The classic go-to is a black cocktail dress, and remember to subtly suggest other sides of your personality. Textured nylons, a funky large ring, or red shoes – pick one and this will bring your playful self forward without saying a word. This evokes a woman of substance and wisdom who has lived a full life and knows herself well. Have fun!

Q: I have purchased a three-piece suit; how do I optimize the vest?

Just gotta say: great investment! One of my favorite standout looks for men is the vest worn with denim and a killer shirt with the same colour palate. If you have a bit of a tummy this softens the silhouette or, as I like to say “area of concern for fit.” For the fellow with a long torso, this can add balance in place of a sports jacket. The vest acts as a break in the linear line. The non-verbal communication a vest relays is that the man is a man of class distinction and style.

Q: I can’t wear wool as my skin reacts, so what can I wear for cozy knits?

If you have an instant reaction to wool, stay away from it and never let a salesperson talk you into buying what doesn’t work for you; you’ll never wear it. There are so many great fabrics on the market that offer a stylish, cozy feeling: cotton, fleece, linen, bamboo, modal and silk are all fantastic options. Bamboo is one of my favourites as it feels like silk, is stronger than merino, is biodegradable and doesn’t retain body scent. Fashion and function – love it!

Q: I have several parties to attend this season and I wish to buy one pair of shoes that will go with everything.
What should I look for?

The first rule of thumb when buying new shoes is to go shopping around 3 p.m. – your feet will be at your true size. Second tip for buying a shoe to fit all looks for the holidays: I love a classic suede kitten heel in black. Sling back, pump or strappy is all about your style choice. They pair perfectly with any dress and will rock a boyfriend jean. Patent leather will scuff easier and does not give as well as suede. The higher the vamp on the shoe (upper section of the shoe) the more support you will have.

Q: I work in an office and with the holiday season here,
I have a few after work parties to attend.
What can I wear that can transition into a killer evening look?

A dress is your best opportunity for transitioning into cocktail party hotness from the office. Wear a shift dress with a blazer, classic pumps and hair up to work. Moving into the cocktail hour, remove the blazer and replace with a sheer shawl, strappy high heel, hair down, evening clutch, sexy lipstick and bling. Always be prepared and have a few of these items at your desk for the last minute invite.

December’s Style Tip: Get your style on by getting your smile on. Tis the festive party season and if you want to look your best make sure you have taken time to have your teeth whitened. White teeth and red lipstick are irresistible! Your Stylist, Shai Thompson

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