JOIN THE 'FRIENDS WITH BENEFITS' COMMUNITY →

  • Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
Style Girlfriend

Style Girlfriend

Helping guys look, feel, and act their best

Search
  • Women
  • Style
  • Grooming
  • Shopping
  • About
    • Meet Megan
    • Community
    • Contact
  • Friends With Benefits
  • Search
Style

Every Guy Can Pull Off Checkerboard Vans. Here’s How

a pair of men's checkerboard black and white slip-on vans set against a grey background

by Megan Collins Updated: March 24, 2025

Products are curated by Style Girlfriend editors. Purchases through our links may earn us an affiliate commission.

There are some things a man of a certain age — ie, voting age — simply shouldn’t wear. A t-shirt that reads “Female Body Inspector.” Square toe shoes. A wallet chain.

But checkerboard Vans? This timeless sneaker deserves a spot in every man’s wardrobe. From babies to teens to grown-ass men, the checkerboard Vans aesthetic just works.

Scout’s honor, you can pull off checkerboard Vans outfits. Yes, really.

Wearing these funky sneakers is, as they say, a vibe. One that shows you don’t take yourself too seriously, while also proving fashion and function don’t have to exist on different planes.

There are some general guidelines to follow. The slim profile and lightweight construction work best in warm weather, and the shoe looks best when not brand-new.

Meaning? Now’s the perfect time to invest in a pair if you don’t have your own already.

Below, check out men’s checkerboard Vans outfits, and shop the best styles for guys:

stylish older man wearing brown and white checkered vans sneakers with blue jeans and a red short-sleeve sweatshirt
@alessandrosquarzi

Wear checkerboard Vans that aren’t black and white

When it comes to a checkered Vans slip on outfit, feel free to think outside of the black and white box.

The classic slip-on sneaker comes in a range of colors, so see what hue speaks to you. You can follow in Jeff Spicoli’s footsteps without walking in his exact shoes.

stylish man wearing black and white checkerboard vans sneakers with frayed hem jeans and a patterned camp shirt
@jms_hrvy_fits

Pair slip-on sneakers with frayed jeans

This outfit is so fun, stylish, and easy-breezy cool.

You know we love a camp shirt here at SG HQ, and paired with a pair of light-wash frayed jeans? You’ve got a go-to off-duty look that you can turn to again and again when the weather gets warm.

stylish man wearing a black hoodie with white jeans and black and white checkerboard lace-up vans sneakers
@triplepape_

Wear lace-up checkerboard sneakers

A cheat code for you: the checkerboard Vans outfit aesthetic doesn’t rely on the sneaker being a slip-on!

If you’re more comfortable in a lace-up, you’ve got that option, too.

stylish man walking down the street wearing olive-colored pants, a denim jacket and checkerboard vans sneakers
@lorenzo_don

Pair Vans checkered slip-ons with pants that aren’t jeans

Denim isn’t your only option here. Reach for alternative styles like workwear pants, cargo pants, or drawstring pants to create a different vibe with your casual sneakers outfit.

Looking to go even farther with your accessories? Add a leather belt.

stylish older man wearing a green short-sleeve sweatshirt over a white t-shirt with blue jeans and checkerboard vans slip-on sneakers with white socks
images: @alessandrosquarzi
close-up of a man wearing jeans, white socks, and black and white checkered vans slip-on sneakers

Wear your checkerboard Vans with socks

You don’t have to sacrifice comfort to the style gods. Socks and Vans go together like peanut butter and jelly!

You can avoid chafing (and stinky feet) by wearing a pair of tall white socks with your checkerboard Vans outfits. Make sure the sock isn’t too bulky to ensure the effect is intentional and stylish, not dorky.

Shop checkerboard Vans sneakers for men:

black and white checkerboard slip-on vans sneakers

Vans

Slip On Re-Issue 98, $85

Black & White Check

Shop Now
coffee and white checkerboard slip-on vans sneakers

Vans

Slip On Re-Issue 98, $85

Coffee & White Check

Shop Now

Vans

Classic checkerboard sneaker, $80

Checkerboard Grape Leaf

Shop Now
golden glow yellow checkerboard slip-on vans sneakers

Vans

Classic checkerboard sneaker, $60

Golden Glow Checkerboard

Shop Now
vans lx era reissue 95 bmx douglas fir lace-up sneakers

Vans

LX Era Reissue 95, $59 (sale)

In Bmx Douglas Fir

Shop Now

Vans

Classic slip-on, $60

In Pop Check Raspberry Rose

Shop Now

Vans

Classic checkerboard sneaker, $60

Color Theory Checkerboard Pure Grey

Shop Now

Vans

Authentic Reissue 44, $54 (sale)

Lx Checkerboard Black & Off White

Shop Now

Check out more men’s sneaker style from SG HQ:

What to Wear with New Balance Sneakers

This 200’s-Era Shoe Is Back

4 Sandals Women Want to See You In This Summer

Yes, Adidas Samba Sneakers Are Still A Thing

Megan Collins

I started Style Girlfriend to help guys look, feel, and act their best.

More articles by Megan Collins

Twitter Instagram

Primary Sidebar

The Latest

couple holding hands and walking

10 Fun and Affordable Summer Date Ideas to Try This Weekend

stylish man wearing a butter yellow knit polo shirt walking away from a white jeep

This Summer Color Looks Smooth Like Butter

men's summer vacation packing roundup

Men’s Summer Vacation Outfits: The Ultimate Packing List

5 Cool Men’s Brands to Know Right Now

Trending Now

  • summer business casual outfit ideas for menGo Sweat-Free in these Men’s Summer Business Casual Outfits
  • close-up of a man wearing white nike tennis shortsThe ’90s Nike Tennis Logo is Back
  • 5 Cool Men’s Brands to Know Right Now
  • stylish man wearing a butter yellow knit polo shirt walking away from a white jeepThis Summer Color Looks Smooth Like Butter
  • side by side images of men dressed in classically elegant "Italian summer" styleThe Guy’s Guide to Effortless Italian Summer Vacation Style
  • cool baby gearIYKYK: The Best Baby Registry Items Dads Need to Know (That Moms Already Do)
Style Girlfriend
  • Instagram
  • TikTok
  • Twitter / X
  • Pinterest
  • RSS Feed

Connect

  • newsletter
  • careers
  • contact
  • advertise

More From SG

  • Friends With Benefits
  • shop our picks
  • read the blog
  • about us

Style Girlfriend may earn commission from products that are purchased through our site.

© 2025 · Style Girlfriend · Terms · Privacy · Accessibility