You’re now in your 40s – or that milestone is in your rear view mirror – so your style should come naturally, right? But, what if you’re still struggling with building a great wardrobe? Especially with some unexpected body changes? Ugh. (Where did that belly come from??) If you have a closet packed with pieces that don’t go together (or anything at all), fads and one-offs, I’ve picked five must-have garments that turn any wardrobe into a solid gold versatile hit. My choices may not be what you expect, but they’ve given me endless options that keep my look fresh, on trend and youthful. I’ll post five more, and then hit up accessories in future posts. 

Party all day. Skirt by JCrew. Photographed at Nordstrom Yorkdale. Artwork Rosalyn Schwartz.
  1. Sparkle for day: By now, you may have a random collection of evening wear gathering dust in the back of your closet. Forgotten taffetas, velvet and glitter can be a treasure trove! Restyle your evening gems or cut them into new garments that you’ll wear around the clock. I bought this rose gold sequinned skirt on major markdown (80% off) at J Crew, thinking that I would wear to a future gala but I doubt that I’ll ever dress it up. I love how it elevates a very basic white tee, navy cashmere sweater by Vince, and Gucci patent boots. Style tip: When there’s this much of a party in one piece, keep everything else super simple – hair and makeup too. 
  2. The perfect tee: You’ll rarely, if ever, see me in a white button down shirt. I don’t own one – not my thing. I have a weird phobia about buttons (don’t ask). My go-to basics are white and black t-shirts. I layer one under just about every jacket. I buy the best quality I can afford – nothing feels better than a super stretchy jersey – and wear them until they literally fall apart. 
Animal patterns are timeless. Photo by Philip Chin.

3. Animal patterns: Leopard, zebra, tiger and more – animal patterns are timeless and trend-resistant. Whaaaaat?? Yup! These can all be worn year after year – truly, they never go out of style. The Zara faux fur topper I’m wearing here is at least 20 years old. I wear it day to night, and with just about any colour. Style tip: As you mature, pare your animal pattern back to just one piece per outfit. For me, that’s either a topper, jacket or pencil skirt only – and never ever a second-skin dress or leggings. Too tight or too much, and you’ll look like Samantha from Sex in the City on a really desperate day. Here, I’ve matched my go-to topper with a lace skirt to create a more interesting textured outfit. 

Jeans have become my go-to trouser.

4. Jeans with everything: I avoided jeans for years because I felt they made me look dumpy. They rarely fit in the waist and always bagged in the thighs. But once I started to experiment with jeans (never basic though), I realized how great they are at balancing my love for pattern and colour. Denim dresses down a statement coat and makes the outfit work for every day. I rarely wear jeans casually – I can’t pull off that effortless white shirt and denim style – I end up looking frumpy. Here, I’ve paired cropped JCrew stretch denim (always stretch) with a versatile animal print shell, patterned light wool scarf, and a Dries van Noten topper. All of the mixing and clashing works because the colours are in the same tone, and my jeans anchor the outfit. Oh, and I love cropped jeans to highlight my footwear collection.

Leather truly goes with everything, including a Wayne Clark cocktail dress. Photo by George Pimentel

5. The versatile leather jacket: Some women collect leather jackets in every shade. I swear by one plain zip-front jacket that I’ve had for at least 15 years. Here, I wore it over a Wayne Clark cocktail dress to a winter gala. It gave the dress a whole new vibe and kept me warm on a  chilly night. I’ve worn the same jacket with ripped and sequinned jeans to a party; and a black pencil skirt to work. It’s brilliant because it’s so plain. Normally I prefer a longer jacket to cover my bum, but this straight cut style (no elastic or band) is simply perfect. 

Style tip: I love this advice that my friend and former boss (Editor of Chatelaine magazine) Rona Maynard shared. Avoid items that tend to be worn exclusively by older women – pieces that you’ve never seen on anyone under 45. Boxy jackets, twin sets and elastic waist straight leg trousers come to my mind. Same for men. Silhouettes change and materials have improved (I need a shot of stretch in just about every fabric.) That old belief – if you hang on to anything long enough, it will come back in style – really doesn’t cut it anymore.

40+ women with strong personal style whom I follow on Instagram: PR master Natasha Koifman @natashankpr; TV host Tracy Moore @thetracymoore; Actress Tracee Ellis Ross @traceeellisross; Vintage collector Cherie Balch @shrimptoncouture; Influencer Grece Ghanem @greceghanem; Stylist Michelle Addison @michelleaddisonstyle; Editor Christene Barberich @christenebarberich