New York Street Style

Vintage Photos of New York Street Style

Of all the celebrated destinations for fashion, no place can come close to the influence and cache of New York City. As the capital of fashion, NYC has always been held in special regard for fashionistas everywhere. That extends to vintage clothing, which has a rich history for its celebration of the past and how it correlates to current fashion trends. Before the advent of social media and platforms to display thousands of photographs that could be viewed by tens of millions of people, there were vintage photos taken in New York City that set the trends that men and women everywhere began to incorporate into their own wardrobes. The following are some photos that have left an indelible mark on the fashion world decades after they were taken.


Nautical Apparel

During the 40s and 50s, America was experiencing a major boom in several industries as the country began to grow at an exponential rate. Influenced by World Wars I and II, nautical apparel was worn by both men and women as a way of showing support for the troops through fashion. The look featured bold block colors, and clean, tailored lines that were modest yet chic.


Previously associated with farm work, overalls made the transition from the plantations to concrete jungles as men and women found a way to take them from their mundane beginnings into the fashion fold. As a more comfortable alternative to the standard apparel for women at the time, overalls underwent radical transformations that are still being seen to this very day.

Mad About Mod

Source: Collage Vintage

Source: Collage Vintage

Fashion took a turn in the 60s that resulted in clothes for men and women that celebrated less traditional lengths and lines, including the ‘mod look’ that became one of the most popular. This leather dress is a perfect example of how the aesthetic was worn then and still today.


Source: pinterest

Source: pinterest

Women in pants became a staple generations ago, and they became an instant hit in New York, where women clamored to emulate the screen sirens of the day that were heavily promoted in the apparel of the world’s most respected designers. Once they became the norm, there was no turning back, and today, women have a broad selection of pants to choose from.


Source: pinterest

Source: pinterest

Having a statement piece was a must for any woman during the 30s and 40s just as today, and overcoats have always been one of the go-to looks for fashionistas in New York. Whether fur or leather or knitted, a great overcoat was and still is one of the boldest ways to make a statement without uttering a word.

Short Shorts

New York City was one of the first cities where women could truly experiment with traditional approaches to dress, and short shorts made quite the entrance during the 60s and 70s as attitudes about hemlines and lengths changed considerably. Today’s woman may opt for even tinier versions of these shorts.

Princess Dress

Source: Monovisions

Source: Monovisions

Inspired by the monarchy and in particular movie icon Princess Grace of Monaco, fashion veered towards the regal during the 50s and 60s, and the princess dress was at the top of every woman’s wish list. This red velvet dress is the perfect example of what women wanted during the era and still turns heads today.

Dapper Suit



The Harlem Renaissance was the birthplace of several iconic styles that still impact the fashion world today, and menswear in particular took a dramatic turn that showcased pleats, plaids, and tailored perfection.


Women’s swimsuits got considerably smaller during the 60s as monokinis and bikinis became the norm. Today, there has been an embracing of more retro looks for swimwear, and these swimsuits can be seen on beaches from Los Angeles to Sydney.

Flapper Fashion

Source: pinterest

Source: pinterest

The Roaring 20s stormed in with a bang on every front, including fashion, with the flapper dress creating a sartorial sensation in New York City and beyond. The look never went away and today, it has taken on a slightly different look, yet still bares the calling card of its initial emergence. More vintage ideas are reflected in movies. Check out Café Society:A Look at Hollywood in 1930s & Mad Men: Throw Back to 60s Fashion Style & Fashion Flashback: Classic European Fashion from Downton Abbey

Triston Brewer
September 30, 2016

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