How to Style Checkered Slip-On Vans and Colorful Sneakers Like a Pro

How to Style Checkered Slip-On Vans and Colorful Sneakers Like a Pro

How to Style Checkered Slip-On Vans and Colorful Sneakers Like a Pro

Hey, sneaker babes! 👟✨
If you’re like me, PiPPY, you know that the right sneakers aren’t just for comfort — they’re a whole vibe. Whether you’re running errands, hitting brunch, or pulling together a casual-cool outfit for that Instagram moment, the shoes can totally make (or break) the look.

Today we’re breaking down how to style two of our forever favorites: classic Checkered Slip-On Vans and eye-catching Colorful Sneakers. Scroll for outfit inspo, styling tips, and links to shop our faves (yep — you’ll wanna add to cart 💸).

🖤 The Iconic Checkered Slip-On Vans

Let’s be real — checkered Vans are a whole lifestyle. They’re edgy, a little punk, a little skater, and a whole lotta cool. But they’re also surprisingly versatile.

✔️ Look 1: Cali Casual

Pair With:

  • Light-wash mom jeans with a raw hem

  • White cropped tank or fitted tee

  • Oversized button-down or flannel (bonus points if it’s vintage or thrifted!)

  • Minimal jewelry (think: tiny hoops, layered chains)

  • Tote bag or canvas backpack

🖤 Why it works: The neutral black-and-white pattern grounds the look while adding a bold pop. It’s effortless cool girl energy.

💬 Style tip: Cuff your jeans to show a little ankle. It keeps things light and lets the shoes shine.

👉 Shop Checkered Slip-On Vans Here

✔️ Look 2: PiPPY Girlie Grunge

Pair With:

  • A baby tee or graphic cropped top

  • Black pleated mini skirt

  • Chunky crew socks (white or a pop color!)

  • Mini shoulder bag

  • A denim jacket or oversized blazer

💗 Why it works: The checkered print adds contrast and pattern to an otherwise clean outfit. It gives Y2K-meets-skater vibes in the best way.

🧷 Try this: Add a hair claw and a stack of charm bracelets to balance the edge with a little sweetness.

👉 Shop Our Favorite Mini Skirts Here

✔️ Look 3: Athleisure but Make it Chic

Pair With:

  • Black biker shorts

  • Oversized vintage sweatshirt or hoodie

  • White crew socks scrunched down

  • Tiny gold hoops and slicked-back bun

☕ Why it works: Vans keep this sporty look grounded while still saying, “I didn’t try too hard.”

👉 Shop Oversized Sweatshirts Here
👉 Shop Favorite Biker Shorts Here

🎨 Styling Colorful Sneakers Without Looking Like a Crayon

Bright, bold sneakers are having a MOMENT. Whether you're rocking hot pink, neon green, or multi-color retro runners, they make a statement — and styling them is all about balance.

🌈 Look 1: Monochrome Pop

Pair With:

  • All-white or all-black outfit (jumpsuit, romper, or matching set)

  • Bright sneakers in your favorite color

  • Slick hairstyle (think braid or high pony)

  • Minimal jewelry and bold lip

🔥 Why it works: A solid base lets your kicks do all the talking.

👉 Shop Colorful Sneakers We Love

🌈 Look 2: Matchy-Matchy Moment

Pair With:

  • Pick one main color from your sneakers and echo it in your outfit (top, bag, or accessory)

  • Think color-blocked sweater or printed mini dress with coordinated tones

  • Chunky socks or leg warmers

💥 Why it works: Repeating a color from your sneakers in the rest of your outfit pulls the whole look together without being too “matchy.”

👉 Shop Bold Sweaters & Mini Dresses

🌈 Look 3: Weekend Cool Girl

Pair With:

  • Slouchy vintage jeans or cargo pants

  • Ribbed tank or sporty crop top

  • Bright sneakers (we love an orange or cobalt!)

  • Crossbody bag

  • Retro sunglasses

😎 Why it works: The loose, laid-back pieces are offset by the unexpected pop of color on your feet. Effortlessly fresh.

👉 Shop Vintage-Inspired Denim Here

PiPPY Pro Tips for Sneaker Styling:

  • Add texture – Mix leather bags with canvas shoes or denim jackets with ribbed knits for dimension.

  • Play with socks – Try scrunchy socks, mesh, or even printed ankle socks for extra style points.

  • Don't forget the accessories – Your sneakers are the start, but rings, sunnies, bags, and hair accessories finish the vibe.

  • Confidence is key – Loud sneakers? Classic checks? You’ve got this. Walk like you OWN it.

Whether you’re slipping on your checkered Vans for that coffee run or lacing up colorful kicks for your next day out, the goal is the same: feel amazing while looking effortlessly YOU. 💕

So which style are you trying first? Tell us in the comments or tag us in your #pippybabe outfits — we’re dying to see how you wear your sneakers!

XOXO,
Pippy

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