Checkmate: How to Style the Checkerboard Midi Two Ways

Checkmate: How to Style the Checkerboard Midi Two Ways

Welcome back to The Ultimate Style Guide! Today we’re obsessed with a piece that brings maximum impact with minimum effort: the Checkerboard Side-Slit Midi.

Patterned skirts can sometimes feel intimidating, but the structured grid of a checkerboard print actually acts as a fantastic anchor for your outfit. This skirt features a flattering bodycon fit, a modest midi length, and a daring side slit that adds just the right amount of movement.

Whether you're feeling the "Cool Classic" or the "Dopamine Brights," here is how to style both colorways.

 

Colorway The Vibe Best For...
Shadow & Bone (Black/White) Edgy, Streetwear, Versatile Concerts, city strolls, and edgy office days.
Electric Orchid (Pink/Green) Bold, Retro, Playful Summer festivals, brunch, and making a statement.

 

1. The Shadow & Bone: The Urban Edge

The black and white checkerboard is a total nod to '90s skate culture but elevated for a modern wardrobe.

  • The Streetwear Standard: Take a cue from the look above and pair it with a faded graphic tee tucked in at the waist. Add a pop of color with bright pink sneakers to keep the look from feeling too monochromatic.

  • The Night Out: Swap the sneakers for black combat boots and add a cropped leather jacket. A slicked-back bun and silver hoop earrings complete this "off-duty model" aesthetic.

  • Pro Tip: Since the pattern is busy, keep your accessories geometric and chunky.

2. The Electric Orchid: The Dopamine Hit

This pink and green combo is for the girl who isn't afraid to be the center of attention. It’s vibrant, unexpected, and high-energy.

  • Clean & Crisp: Balance the intensity of the pink and green by pairing it with a simple white baby tee and clean white sneakers. This lets the skirt do all the talking while keeping the overall look fresh and summery.

  • Maximum Color: If you're a maximalist, lean into the green! Pair it with a forest green knit tank top and some platform sandals.

  • Pro Tip: Use the "sandwich method"—match your shoes to one of the colors in your top or the skirt to create a cohesive flow.


Three Rules for Styling Checkerboard

  1. Mind the Scale: If you wear a patterned top with this, make sure the print is much smaller or much larger than the checks on the skirt to avoid a visual clash.

  2. Highlight the Slit: Since this skirt has a side slit, opt for footwear that flatters the ankle. Low-top sneakers or strappy heels work best to elongate the leg.

  3. Tuck it In: To maintain the sleek silhouette of this midi, always tuck in your shirt or opt for a cropped length to highlight your waistline.


Are you Team Classic Black or Team Electric Pink?

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