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Dior’s creative director, Maria Grazia Chiuri, wears a work look that is classic and pragmatic: Roomy pants and a relaxed blazer are investment buys you can wear this season and beyond.Kristy Sparow/Getty Images

As more of us start heading back to the office with some regularity, the question of what to wear to work is more pressing than ever. So much of our pre-pandemic office wardrobes are either out of style, don’t fit anymore or feel like relics from another era, one where we willingly endured uncomfortable heels, hard pants and lengthy daily commutes.

To prepare for a stylish return, it may be tempting to turn to pop prints and fast fashion to add newness to your wardrobe. But with hybrid work life the new normal for many of us, it’s a better bet to invest in timeless, all-season pieces that are equally luxe, comfortable and polished.

“It’s definitely about the investment pieces at the moment, those classic pieces that can transcend trends almost and work across your wardrobe,” says Laura Yiannakou, senior womenswear strategist at the trend forecasting company WGSN. “Consumers are now looking for pieces that can perform multiple functions.”

Versatility and longevity are key for a moment like this, when there are so many uncertainties about what work itself may look like moving forward. “I want to get things that are really versatile, that I can travel with, that I can go to business meetings with, that I can also wear comfortably if it’s just going to be a day in the office,” says Zohar Levy, a commercial litigation lawyer in Toronto. “I don’t think, at least in my line of work, that it will get back to where it was when I was a junior lawyer and wearing suits every day … at least not for a long time.”

Levy, who has been working part-time in the office, bought a pair of boots and some well-cut dresses in what she describes as “forgiving fabrics” last fall, but otherwise is still trying to work out what her office wardrobe will look like in the months to come. “I just really don’t know what the future is going to hold,” she says. “How often am I going to go in? How formal is the office going to get? But also, as my activity level picks up, what am I going to fit into, and how are things going to look on me?”

A solution? Looking at what you already own that still fits and makes sense for your current routine. For Levy, that meant trying on everything, doing a wardrobe clean out and identifying the items she would wear to the office now, and then looking to supplement with a handful of smart acquisitions that effortlessly fill in the gaps.

Mercedes Boykin-Sabalones, area sales manager at Nordstrom Canada, recommends starting with a great relaxed blazer, and an oversized, collared shirt. Both can be worn across multiple seasons and styled in different ways with trousers, jeans or even leggings. Plus, if you go for an unexpected hue like baby blue or lilac, even a timeless cut can feel fresh and vibrant.

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A relaxed blazer can be worn across multiple seasons, and offers a bevvy of diverse styling options. A.L.C. Dakota One-Button Jacket, $890.

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An oversized shirt in an unexpected hue can freshen up your back-to-work wardrobe. COS Oversized Shirt, $125.

A pair of comfortable, relaxed-fit work pants ( is another must-have. “Nobody wants anything too tight anymore,” Boykin-Sabalones says. She recommends a wide-leg pant, or tailored trousers with an elastic waistband – both are easy to wear but dressier than sweats or leggings for the boardroom, and beyond.

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Wide-leg pants combine office-appropriate sartorial savvy with WFH-level comfort. Elisa C-Rossow Vesper Wide Straight Cut Pants, $425.

Noting that dresses are starting to trend again after some decline as a category during the pandemic, Yiannakou suggests adding a rib-knit tube dress that’s knee-length or midi to your shopping list. The beauty of this type of bodycon silhouette is that it can easily be dressed down with a loose cardigan or sweater over top, then dressed up for the office with a blazer and heels. “It’s about pieces that you can layer up, layer down according to either the climate or the setting that you’re in,” she adds.

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A ribbed bodycon dress can be dressed up or down. Loulou Studio Kale Ribbed Midi Dress, $610.

Finally, you may want to seek out classic workwear pieces made in an extra comfortable fabric. “Jersey was always associated with activewear and slightly more casual looks, but we’re seeing these beautiful, heavy, luxe jersey weights come through that are really starting to elevate dress, top and skirt styles,” Yiannakou says. Whether it’s a tailored dress or bootcut trousers, seek jersey styles that look formal but still offer ease.

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Structure and cut make this top formal enough for the office, but its jersey fabric still lends comfort. Judith & Charles Xenia Top, $245

Comfort and versatility both feel key at this moment, when so much about work itself feels in flux, and your wardrobe has to stretch beyond your office walls, too. “The lines that did once divide work, leisure and pleasure within womenswear … have been largely erased now,” Yiannakou says.