Fashion Week Wisdom from PicMonkey CEO Jonathan Sposato

It’s Paris Fashion Week, cats and kittens! And this past week was both Milan and London’s fashion weeks, and just the other week it was New York Fashion Week, and in short, we no longer know what the word ‘week’ means.

But one thing is crystal clear: it’s that time of year when we celebrate aesthetic innovation and great style, traditionally through lots and lots of glossy photos. In honor of the occasion, we’d like to present a buffet of sartorial wisdom from a man who lives every day like it’s fashion week: our CEO, Jonathan Sposato.

We partied on Instagram with Jonathan all NYFW as he shared some of his favorite looks and style tips. Now, he bedazzles our humble blog with his presence, and lets us in on a few of his fashion secrets.

Fashion secret: wear white after Labor Day

“Part of having great style means knowing yourself well enough to know which rules you can break,” Jonathan told us casually in the kitchen one morning.

In the case of the outfit above, breaking one rule helps Jonathan follow others. Sticking to one color means you can play with patterns and texture, as he does above in his post-Labor-Day-white look.

Fashion secret: match your watch to your outfit

Don’t all watches match every outfit? this reporter asked naively. Not so! In fact, watches make the perfect splash of accent color, like brightly painted fingernails or a piece of jewelry. Dip your toe into the world of watch-and-outfit-matching by picking a watch with a colorful face—say, red—to match the red stripes on your shirt, or a dashing red handkerchief.

Conversely, you can keep your colors scrupulously consistent. No matter the hue, monochrome always makes a striking statement.

By the way, did you know there’s such a thing as tropical watches? And we’re not talking Hawaiian print: some vintage watches are made of materials that changed color under the effects of time and weather, turning from black to a rich milk-chocolate color.

That’s not necessarily a fashion secret, but it is a cool historical thing Jonathan told us.

Fashion secret: discipline doesn’t mean boring

We’ve all heard that the big designers wear all black. But is that what a “disciplined look” really means? Jonathan thinks no. For him, dressing with discipline means paying close attention to what makes him happy.

Here’s an example: Jonathan loves the idea behind capsule wardrobes. Direction! Focus! Seasonality! These are all great qualities. “Nothing dilutes one’s stylishness more than lack of focus,” he told us.

However, the discipline of a capsule wardrobe shouldn’t keep you from flaunting the style that makes you feel your best. Jonathan believes his own wardrobe contains not one, but three capsules:

Hollywood Dapper. Cary Grant was one of Jonathan’s original style icons in college, where he was pleased to develop a personal style that nobody else his age was rocking by learning about textures, suiting, grooming, and accessorizing. This look involves tailored suits, sweaters and ties, and pocket squares galore. Generally? It’s natty as heck.

Streetful Sporty. Streetful may not be a real word, but that shouldn’t detract from the cred of this look. Just like young hearts that run free, Streetful Sporty clothes don’t take themselves too seriously; Jonathan branches way out from the norm with futuristic knits, ambitious minimalism, and, every now and then, double pants.

Atomic Lounge. Rather than being inspired by a person or an established style, this look comes from a place: Palm Springs of the ’60s and ’70s. Playful jumpsuits, lighthearted patterns that evoke a groovy vibe, and bright colors abound. (As just one example of Atomic Lounge, Jonathan pointed toward clothier Mr. Turk, which has recently put out suits that look as if they could be made from vintage couch covers.)

These three style groups are focused, but balanced—in the part-of-a-balanced-breakfast sense, with a banana and OJ but also some sugary cereal. Jonathan doesn’t have to throw away his favorite prints to live a monochrome monastic lifestyle, but he also isn’t adrift in a sea of clashing clothes.

Fashion secret: let your clothes talk to each other

Fashion magazines tend to pay lip service to the notion of timelessness, while lobbying hard for the trend du jour. Jonathan points out, though, that iconically fashionable people often buck the trends of their day—or at least, have no particular allegiance to them.

“Though not trendy specifically to their time, decades later, photos of them still look amazing,” he told us, of style heroes Grant and Dean Martin.

Jonathan gives a nod to these eminently cool cats—as well as to the notion of timelessness in general—by mixing vintage and modern pieces. The “conversations” this creates can be as simple as a decades-old watch paired with a brand-new suit, or a little more complex: like combining a vintage army jacket with new distressed pants.

“The pieces share a vocabulary of zippers and rugged,” Jonathan explained, as well as “masculine utility.”

How can you create your own clothing conversations? Start thinking about what your clothes have in common. This could be colors or patterns, but it may also be a mood. For instance, a ruffled skirt from Forever 21 and a tie-front blouse from the ’70s may share a frilly sensibility that makes them a good match.

Fashion secret: unlock your confidence by finding a style icon

Sing out if you’ve heard this fashion truism: “Confidence is key!”

Well sure, you might think to yourself, of course confident people can wear anything they want; they don’t care what anyone thinks! Most of us, however, weren’t born with an inner wellspring of self-satisfaction, so what to do?

Jonathan also happens to believe in the sartorial value of confidence. But he thinks that confidence, rather than something you cultivate in a vacuum, comes from a confluence of factors. Maybe you need to be in shape to feel truly confident. Maybe you need a positive outlook for the future. Maybe it’s your accomplishments or skills. And for those of us who still aren’t entirely sure who we are and how confident we feel, Jonathan provides an important addendum: one way to start exploring the upper regions of self-esteem is to find a style icon.

When you think about it, it makes sense. Finding someone you want to be (or at least, whose wardrobe you want to steal) can help you figure out your goals, stylish or otherwise. And when you have a style icon, it justifies fashion choices you may not, at first, feel confident enough to go for. Plus, the benefits may extend past what you wear. When Jonathan started emulating Grant, he discovered that dressing up is, for him, a form of respect: he gave that respect to others, and got it back from them.

Pro tip: You don’t have to pick just one style icon. Above, Jonathan channels Steve McQueen, but there’s still room in his closet for Cary. Maybe you want Marilyn Monroe’s bikinis, Solange Knowles’ mastery of prints, Che Guevara’s hair, and a unicorn’s heart. Do you! Or whoever you think “you” might wanna become.

Elisa Chavez

Elisa Chavez is a content writer here at PicMonkey, where she hopes to change the world one dinosaur selfie at a time. She is also a nationally ranked slam poet, champion shopper, and doting dog mama.