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Many designers and retailers are blurring once-rigid gender lines.Illustration by Sarah Farquhar

A few years ago, I found myself coveting a floral-print jacquard shirt from New York-based label Engineered Garments’ men’s-wear selection. The piece in question – which I bought after tracking down a size extra small – has a boxy fit, a row of buttons on the right side instead of the left and two pockets across the chest, details you usually find in the men’s section.

The shirt is now one of the most complimented-on items in my wardrobe and has caused me to double down on an approach to dressing that, like many designers and retailers today, blurs once rigid gender lines. If you’re pondering pieces classified for a gender outside of how you usually shop, two fashion professionals sound off on what to keep in mind.

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You Do You

Christina Pretti, founder and creative director of the Toronto shop Soop Soop, says to start with two simple questions: What do I like and how do I want a piece to fit me? “It seems so obvious, but people can struggle with it,” Pretti says of how traditional gender tropes have affected our opinion of what looks we can wear. “People forget they have agency and don’t put personal taste into the equation.”

In addition to exploring the entirety of a store’s inventory and turning to a brand’s customer service representatives when questions arise, Pretti emphasizes that if something doesn’t fit you perfectly when you purchase it, there are many ways to tweak it. Relatively inexpensive tailoring jobs such as taking up a hem can take a garment from good to great and often costs about $5 at your local dry cleaner.

Shoes Clues

Footwear has a more gender-neutral metric compared with clothing – if you’re shopping in European sizes, that is. “European sizes run from a 36 to 46. It’s not like U.S. sizing that says a women’s nine is a men’s seven,” says Pretti.

“I’m looking at common adult sizing,” says Pretti about footwear stock at Soop Soop, which are labelled with quotation marks to highlight the conventional gender designations assigned to fashion items.

Not All Cuts Are Equal

One thing that immediately struck me when I tried on my beloved Engineered Garments shirt is how squarely cut the torso is. I own many blouses and have become accustomed to how they accentuate curves. “A men’s shirt usually won’t shape the body the same way,” says Juliana Schiavinatto, a stylist and founder of the new upcycling-centric brand Re-pull.

She notes that women’s shirts typically taper whereas men’s are more linear in silhouette. And darting – the technique of folding in and sewing up excess fabric to create shape – is more common in women’s wear. When it comes to sleeves, you’ll often find a snugger fit in women’s shirts.

Think About Fabric

“We get dressed every day and yet so many people don’t think about their clothing in terms of the fabric,” Pretti says when asked about whether materials play a part in finding a good fit. She offers the example of denim, where a raw or 100-per-cent cotton fabric will potentially be tighter or more restrictive than jeans that incorporate elastane.

Size Matters

When it comes to finding the right size across gendered designs, Schiavinatto culls advice from both personal and professional experience. “If I’m shopping something from a men’s-wear collection, I’m buying down one to two sizes,” she says, but adds that sizing differs so much from brand to brand that it can complicate this strategy.

That’s why she says it’s key to look closely at a specific product’s measurements when purchasing online so you can make a more informed decision and avoid a return. If the information isn’t readily available, e-mail customer service and ask for the basics: shoulder, chest and sleeve length up top and waist, hips and inseam on the bottom.

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