You'll never like you look like someone's grandmother (even if you are - amazing!) with a few simple statement pieces

Over the years I’ve learned that the difference between personal style and awkward (or no style at all) looks comes down to a few key pieces and the right accessories. The perfect hat, just the right bag and awesome jeans create your style signature. But it’s a fine line. Too many accessories and you can look like you tried WAY TOO HARD. Not enough of the right kind and you’ll look bland. Or accessories from another era (either your closet or a vintage rack) can make you look like a relic. I’m wary of accessories with pizazz (think jazz hands – no please don’t actually); anything too crafty (think granny’s tickle trunk); or a whole lot of fuss (check out the mirror as you leave and take most of them off). The key to looking cool is a mix of simplicity, texture and your own confidence. Read on about a few of my favourite pieces:

SEQUINNED JEANS, A FEDORA & AN ANIMAL PATTERN BAG – One of my go-to outfits this fall and winter will be the outfit above -my favourite Anthropologie jeans (should have bought every pair in my size three years ago), a basic white tee, and a black sleeveless topper by Dries van Noten that I picked up this past spring. It’s a simple look that’s a perfect backdrop for accessories that truly capture my style. And this one starts with my hat by Toronto designer Karyn Ruiz of Lilliput Hats. This outfit falls flat without it. I’ve never worn hats because I could never find one big enough. I finally visited Karyn’s boutique on College Street and had this grey fedora custom made.

Style tip: To keep it cool, I suggest a simple hat designed to complement the shape of your head in a neutral shade (black to fawn) with a simple leather band. My hat doesn’t have a full crown because it would look like a flying saucer landed on my head.  A quirky shape accented with buttons, beading and big feathers will make you look like the Queen. PS – you’ll never catch me wearing a fascinator in this lifetime. The fuss and fanfare of a fascinator ages you fifty years in a flash.

To complete this simple look, I added a forgotten leopard pattern YSL bag (from the Stefano Pilati era) and striped heels by Aquazzura. The unexpected mix of textures and patterns adds personality to this weekend ready outfit. I’ll substitute skinny black trousers and a black slouchy tuque to wear it to work.

Style tip: To keep it cool, wear a maximum of two animal patterns at any time. Try a bag and shoes, or shoes and a sweater. Too much animal print – a dress, shoes, a scarf, and a jacket  is too much. 

Here’s the bag again … you will never go wrong with a leopard pattern bag, belt or pair of shoes (sneakers, flat, heels, boots – anything!) Leopard is a neutral and looks chic with anything at any hour of the day. Trust me. Here, I’m wearing it with my all-time favourite topper – the first piece I bought by my now favourite designer Dries van Noten. I had to walk around Fifth Avenue in New York twice hyperventilating while I tried to justify its price. Best investment ever. You may be tempted to wear a simple navy handbag with this coat of many colours. Don’t. Leopard or a metallic is unexpected and looks more artistic. 

Photography, Tara West

What did I tell you about those jeans? I LOVE them – and here they are again. This time with another favourite Dries van Noten topper. The other elements here that keep the look fresh are the leather flower necklace by Marni and the classic Rayban aviators. You simply can’t go wrong with this classic frame – it’s not showy so it doesn’t take over your face – aviators remind me of Top Gun with Tom Cruise. Simple and sexy – and it looks great work to weekend.

Style tip: Wearing sunglasses indoors only works if you’re Anna Wintour. And while she may want to hide her expression (and under eye bags??), it looks silly to me. Avoid bedazzled frames (I want to look chic, not quirky), and never, ever, wear them strung around your neck.

Photography, Tara West

METALLICS – Here’s the Dries van Noten topper again with Vince striped trousers (always slimming as they lengthen the look of your legs) and silver Prada sneakers. To keep it cool, try novelty sneakers in a versatile metallic – I prefer silver. The fashion-forward 20somethings may be wearing chunky “Dad sneakers” but I’d look ridiculous in those big molded plastic shoes – think Working Girl with Melanie Griffith. (Kids – Google it). My other option is plain white sneakers – anything more is one trend that could make you look like a throwback to your high school era – and who wants that??! Add high-waisted jeans and tuck in your sweatshirt and you’re right back in the 80s. No thanks.

Style tip: To keep it cool, your sneakers should look more sophisticated than athletic. They’re a much more fashionable choice than ballet flats – and way more comfortable. 

Photography, Tara West

CROSSBODY BAG: A small hands-free bag that holds your essentials (phone, credit card, lipstick and keys) is your every day essential. Ditch the heavy handbag that you may normally carry everywhere in favour of this versatile option. I love this Louis Vuitton mini (the red top adds a cheeky accent) and my other favourite is in a silver metallic. 

Style tip: An of-the-moment handbag quickly elevates and updates your whole look. A sturdy practical bag would weigh down my look. The vibe here is modern, active, on-the-go which gives you an overall youthful spirit. This is not the time for a serious top-handled purse or shoulder bag.

And the main ingredient to keep your 40plus style looking cool? Confidence. Find a look that works and then invest in top quality pieces that express that signature. It took me a long time to find my style – colourful patterns mixed with body-skimming basics and chic accessories. I loved experimenting but now I feel totally comfortable with my own fashion code. And I always love it when a friend describes something as a “Lisa look”. Mission accomplished.