Comfy Holiday Checkerboard Glam

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Story by Ashley White of Le Stylo Rouge     |     Photos by Sabrina Osborn

Welcome to the holiday season, Kansas City! Juicy turkey, Plaza lights, Christmas cocktails – they’re all in our very near future and I can’t wait. With so many events packing the holiday calendar, what’s a girl to wear?

I love pairing different trends and textures and there’s definitely a lot of that going on in this look. Let’s start with the mix of casual and glam: a comfy oversized cardigan paired with a fancy, feathered stiletto.

This over-the-top cardigan is the focus of this outfit, with its checkerboard print (a big trend right now!) in a festive green-on-green palette. Merry, merry indeed! I threw it on over a simple black turtleneck, invoking some serious coziness via light layering.

The stiletto, on the other hand, is all about fun, almost-impractical glam. Perfect! I wanted the shoe to be one thing: gorgeous. It didn’t need to be particularly functional; it just needed to make a beautiful statement. The tall heel and flouncy feathers dress up the rest of the look nicely – just don’t wear them to Christmas dinner if it’s sleeting or snowing!

Tip: if you’re celebrating at a friend or family member’s house, stow a pair of chunky socks in your bag and slip into ‘em as the festivities wind down. This allows you to shift into full comfort mode without going barefoot. Bonus points if the socks have an on-brand theme, like peppermint stripes, tiny trees, or just a bright hue in a holiday color.

More comfy glam contrast here with my trouser choice: a pair of satin joggers. Lots of room to move (and eat!) in these joggers, but the black satin weaves a luxurious element into the mix. They work to tie in the cardigan and stilettos seamlessly!

Glam jewelry amps up the formal factor, with sparkly studs, a tennis necklace, and a long, knotted chain lariat. I really like the way trendy (checkerboard print) and timeless (classic jewelry) come together here. A holiday must – the red lip – and a gold clutch help elevate the outfit.

I love the way this look comes together for a festive feel that doesn’t totally sacrifice comfort. Why, yes, you can have it all – at least when it comes to holiday fashion!

Wishing you a lovely holiday season, KC!

You can find Ashley at or on Instagram at @ashrockchalk

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