Your Instagram Guide to Mastering Street Style

When it comes to perfecting your sartorial street cred, one of the easiest and most influential places to turn is the infamous, hashtag-laden social-media stream of Instagram. The handles of @thesartorialist, @thealexbadia, @menwithstreetstyle, @menwithclass, among many others come equipped with no shortage of #nofilter #streetstyle inspiration.

Feed into the social hype and follow this list of trending, street-style themes and Insta-wisdom. You’ll be ready to hit the sidewalk for your Insta-close-up in no time.

1. Distress call

Street style

Street style | Source: @phillippegazarstyle via @menwithstreetstyle (left)/@menwithstreetstyle (right)

This is one SOS you’ll want to answer. Those well-worn, hole-laden, sufficiently distressed jeans that you’ve cast aside in your closet are ready for their street-ready revival. Tattered and torn denim gets a new lease on life when paired with a tailored blazer and prep-star shirt.

With this trend, it’s all about creating the balance between that edgy, ripped, and shredded attitude and polished panache. Think of it as party on the bottom, business on the top. Look no further than Phillippe Gazar who so handsomely demonstrates his version of the distress call in a crisp white button-down shirt and printed tie with faded, tightly fitted jeans — the ink is optional but if you’ve got it, flaunt it.

2. Play with proportions

street style

Play with proportions | Source: @francescocostagliola_ via @menwithstreetstyle (left)/@menwithstreetstyle (right)

The long and short of this sartorial story is a proportions game, and tucked-in shirts have no place in this fashion tale. The street-savvy look dictates a top that extends way below the waist worn with pants or jeans that are cropped and rolled above the ankle.

It’s an unexpected yet trend-forward statement that breaks a few fashion rules. But that’s OK because you never played by the book anyway. Take a cue from the style file of brand consultant and menswear influencer Francesco Costagliola who never met a long tunic shirt he didn’t like — and his looks are all the better for it.

3. Tee time

street style t-shirt

T-shirts | Source: @kye_DArcy via @le21eme (left)/@le21eme (right)

Once relegated to one-wear-only status at questionable rock concerts, printed T-shirts boasting bands, album covers, and other imagery now function as a means to turn up the volume on your look while contributing vintage, cheeky flair. Best to wear them fitted, preferably tucked in, to a pair of chinos or dark jeans — extra points for throwing a blazer over the top — to avoid looking like a groupie. After all, you’re cool enough to be with the band.

Multi-hyphenate artist-skater-surfer-model Kye Darcy used Pink Floyd inspiration to add plenty of rocker noise to his standard-issue, prepster trousers, but feel free to channel any music genre you please.

4. Monochromatic mood

street style monochrome

Monochromatic outfits | Source: @marchettisimone via @le21eme (left)/@thesartorialist (right)

The gravitational pull of the unicolor sartorial universe is unmistakable, where the strength comes not in multiples but in single shades. Show your true colors — make that color — and take full advantage of the whole Crayola box. Monochromatic moments weren’t meant for just black and white. One of our favorite solo-hued sightings of late has been Simone Marchetti’s sporty-refined display of rich, ruby red. But if you’re not quite ready to embrace such a daring hue, start with easier tones of navy blues.

5. Denim on denim

Denim on denim street style

Wearing denim | Source: @menwithstreetstyle (left)/@menwithstreetstyle (right)

We generally wouldn’t advocate for having the blues, but this is one case where it’s completely acceptable. Denim on denim is all about fusing different gradations of twills — and don’t worry about the impossible task of matching them. The mix creates a dynamic off-duty offering. It also fits right in with a few other street-wise trends; for example, ripped jeans are a natural no-brainer here. To go with all that denim, you may want to step out in a pair of bright white sneakers for a crisp, cool-kid finish.

6. Bold suits

Bold Suits street style

Bold suits | Source: @jprstyling (left)/@melodiejeng (right)

The business suit meets the kaleidoscope with this street-style lesson in making your own bold moves. Black, navy, and gray have their place in the color spectrum of the ubiquitous sport coat and pants. But it’s time to up the ante with a bright rush of color that will stop traffic right in its tracks. In this land of technicolor, the glorious punch of a cerulean-blue suit or a goldenrod get-up is par for the punchy course. Caution: You will attract attention — for all the right reasons, of course. Don’t say we didn’t warn you.

7. Leather love

Leather street style

Leather | Source: @menwithstreetstyle (left)/@menwithstreetstyle (right)

Even if you’re not racing around town in a motorcycle, it doesn’t mean you cannot dress for the ride. A surefire way to put a tough-luxe twist into any look is with a black leather zipper moto jacket — the more zippers the merrier. These jackets may have a HOG mood but their main calling card is a devil-may-care, rocker edge.

8. Mix it up

Mixed Prints street style

Patterns and prints | Source: @melodiejeng (left)/@thealexbadia via @thesartorialist (right)

There’s no need to quell your inner mixologist who, in addition to shaking up a mean martini, loves to muddle up different prints and patterns in one outfit. The genius of the look is in its incongruous elements that ironically pull it all together. WWD fashion editor and M fashion director Alex Badia stepped out in an eclectic conglomeration, proving that the geometry of circles and stripes need not match.

One key to successfully stirring up divergent patterns without too much chaos is to ensure each of the piece is from the same color family. A whimsical, textural yellow and navy tunic coat is mighty fine with a printed yellow and gold shirt underneath.

Follow Rachel on Twitter at @rachellw and on Instagram at @rachellwatkins

More from Gear & Style Cheat Sheet: