Men’s wear expert Derek Guy would like you to take more risks with your workwear: ‘There are very few rules’

“Men’s fashion in general has never been better in terms of what’s possible. But it’s never been harder to dress well because there are so many options,” Guy tells Fortune. “It used to be you go to a good store in your neighborhood and they sold you the whole look. Now you have to buy things from all over. It’s very hard now to dress well.”

So what does Guy suggest for those struggling to dress for the office? There’s no one answer for everyone, of course—much will depend on the field, city, position, and even individual office. But generally, Guy says more men should dress in a way that makes them feel good. That might mean casting off the chinos and puffer vests and embracing new brands and styles.

“There are very few rules at this point,” he says, adding that it’s easier to take risks, even by doing something as simple as swapping out a white shirt for a blue one. The possible repercussions for branching out are the least severe they’ve ever been.

“You just have to accept that if you want to dress nice, you’re going to stand out, and it’s not that big of a deal,” he says.

How to experiment with your style

One thing Guy says stops men from experimenting is not knowing where to turn for inspiration, or even what’s available. For those interested in honing their personal styles, he suggests making more creative use of platforms like Instagram.

Someone interested in 1980s punk fashion might find a brand that does the aesthetic well, follow them on the social network, and then explore their tagged photo section. From there, they will be able to find other people whose style they like, and then follow them to see what other brands they wear, using the bookmark feature to save the most inspiring posts.

“Essentially what you’re doing is building a mental library of images that you like,” he says. “Over time you’ll notice that guys tend to wear slightly more cropped jackets and high rise pants, or they wear a certain fabric or texture. You figure out the language for the look that you want.”

Then, start trying out a piece or two from the style you’re interested in. This doesn’t mean swapping out your entire wardrobe at once, he says; but maybe trying a different cut of jeans or jacket to see how it makes you feel.

At a basic level, Guy suggests investing in: A tailored sport coat (in a color like navy), gray or tan wool trousers (swapped out for chinos or jeans if those are too dressy for the office), tailored dress shirts or polos, a textured sweater, and high-quality leather dress shoes. Outerwear, especially, is a good place to invest more money than you might normally be inclined to; for those in hotter climates, higher-quality shoes are a good bet.

“Outfits look better with a layering piece, and a jacket makes the waist look slimmer and builds out the shoulders,” he says. “It’s just a flattering garment.”

It’s important to pay more attention to the cultural relevance of clothes, and less attention to trends, he says. Adidas Sambas are having a trending moment, but they also have a long history in sports and hip hop communities. Knowing that history means they “will always be cool, because that history is cool.”

“Don’t think, ‘does blue go with green,’” he says. “This is not a science project. Think of it as a cultural language. Fashion is this weird thing where it’s a way for us to express our identity but also explore our identity.”

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