80sfashionworld.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com. As an Amazon Associate we earn from qualifying purchases.

Converse sneakers were the shoe of choice for 1980s kids; picture worn-out Chuck Taylor high-tops worn with white tube socks. Even today, in our 2020 world of millennial fast fashion and festival get-ups, Converse is still a firm favorite brand. 

However, there are more ways to style these timeless kicks than casual jeans and tee. Yup, they can even be worn at work and sometimes even at cocktail hour. 

Let’s explore different ways to style Converse sneakers with killer outfits in 2020.


The look: Converse, cropped jeans, and bodysuits

Celebrity Inspiration: Khloe Kardashian (whether you love or hate the K fam!) is the Queen of cropped jeans and tight bodysuits. While Khlo wears the look with heels, we can tone it down with Converse. 


  • Pick form-fitting jeans in stretch denim and a high-waisted cut 
  • Style it up with an embellished or bold-printed bodysuit for juxtaposed denim and sparkle 
  • Pair your Converse shoes with metallic socks for a peak of texture 

The look: Converse, pencil midi-skirts, and blouses  

Celebrity Inspiration: the pencil skirt is a workwear essential, celebrating curves while offering a professional length. Jennifer Lopez, Chrissy Teigen, and Beyonce have all rocked pencil skirts to show their killer bods, often with fitted sweaters, graphic tees, and heels. 

Let’s shake it up and wear our fitted pencil skirts with a tucked-in blouse and Converse. The contrast of business-chic styling with street-ready footwear is effortless and modern, but also very reminiscent of Melanie Griffith in classic 80s movie ‘Working Girl’.


  • For winter, look for pencil skirts in a robust fabric such as thick cotton, lined velvet, or even leather for extra warmth and seamlessness when worn over tights
  • For summer, try a satin or silk bias-cut pencil skirt 
  • Channel 1980s New Romantic style with a soft, ruffled, voluminous blouse and tuck it into the skirt’s waistband 
  • Pick fresh white Converse and wear with ankle socks or stockings 

The look: Converse and overalls 

Celebrity Inspiration: overalls are determined to stay in fashion, and we’re happy about it. While many modern-day celebs have been papped wearing denim overalls, we’re looking back at the 90s in an early season of ‘Friends’. Rachel Green (played by the radiant Jennifer Aniston) wore black overalls, white sneakers, and a tight white striped tee.

In another episode, she wore baggy blue denim overalls with a pale tank top and sweater tied around her waist. These classic casual Rachel looks are equal parts cute and street. 


  • Flatter your body with a flared-leg denim overall that is fitted around the hips and torso
  • Refine the lines with a fitted, cropped overall that hugs the body and showcases the sneaker 
  • Trawl the thrift stores for men’s denim overalls for that classic baggy fit, and pair with a contrasting floral, ruffle-trimmed tank and black and white chucks 

The look: Converse and embellished party dresses 

Celebrity Inspiration: back in the 00s and early 10s, Kristen Stewart rocked the party-dress and Converse look time and again. This look is perfect for girls who love to get glam and glitzy but cannot part with their comfy, worn-in sneakers, refusing to do uncomfortable heels.

The look is not only practical but it’s rebellious and resists the expectation that we should tottle around on high heels as soon as we put on a cocktail frock. 


  • Shop for vintage cocktail dresses with beading, sequins, and metallic fabrics 
  • Channel 80s prom queens with short, tight, ruched dresses with puffed sleeves and sweetheart necklines 
  • Wear your Chucks without socks in summer, and with fine fishnets in winter 
  • Keep the hair Madonna-messy and the eyes morning-after smudgy and dark 


Best Turtleneck Outfits And How To Accessorise Them

The Best Mini-Skirt Outfits and How to Accessorise Them

10 of the Best 80s Skater Trends and Looks…

13 of the Best ways to Style Overalls…

14 Lingerie Trends of the 80s that are still trending today…

The look: Converse, bike shorts, and cropped hoodies 

Celebrity Inspiration: the bike shorts trend has burst onto Instagram and festival fields in recent years, thanks to Kim Kardashian and hubby Kanye’s fashion line. While this look is certainly not for everyone, it has its place. For casual weekend daywear, light exercise, or festivals, it doesn’t really get comfier than knee-length bike shorts, a boxy cropped hoodie, and Converse. 


  • Pick thick, supportive bike shorts with a high, tummy-controlling waist and mid-thigh length to prevent chafing 
  • Look for a raw-edge hoodie or zip-up sweater with an oversized, boxy fit you can sling off one shoulder 
  • A cropped hoodie or sweater showcases the booty and a slither of the midriff 

The look: Converse, slip dresses, and blazers

Celebrity Inspiration: fashion hero Rihanna has been seen wearing silky slip dresses paired with boxy blazers and oversized jackets multiple times. The contrast of silky and skin-skimming with robust and oversized is a quintessential streetwear staple. You can always recreate this look but this time put you Converse’s on!

Hailey Bieber was spotted wearing a red slip dress, chunky leather jacket, and white sneakers with white socks. It’s the 90s, 80s, and 2020 all rolled into one comfy, sexy, and cool get-up. 


  • Bias-cut midi slip dresses are sweet, feminine and flattering on most shapes without constricting the body
  • Look for natural fibers such as 100% silk for summertime breathability and comfort 
  • Search the second-hand stores for men’s blazers or suit jackets, or even bomber jackets you can tie around the waist when it gets hot 
  • Add texture and interest by pairing your sneakers with metallic or sequin-embellished socks

Fashion Tip: Make the look your own by wearing Converse’s!

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

Related Posts

Leave a Reply

Your email address will not be published.