Letterman Sweater: Vintage, similar here and here | Green Corduroy Pants: Massimo DuttiEarrings: Madewell | Shoes: Fila Disruptor 2 | Bag: Italy purchase, similar herechunky sneakers trend

Okay, now I’m excited about fall. I’ve hit that end of summer wall where I am tired of sandals and linen. I never thought those words would come out of my mouth, but there ya go, I said it. I’ve been enjoying this last bit of sunshine we’re getting and in the meantime slowly building up my fall wardrobe. I’ve even considered taking a break from pedicures – too soon? Maybe, too soon.

Obviously, I’m working a few pieces of my summer wardrobe into fall (or at least planning on it!). But – this shouldn’t come as a shocker – I’m starting to add items as well! One of the first items I’ve added? The ultimate pair of chunky sneakers – the Fila Disruptor. YUP…I’ve jumped on the chunky sneakers trend. It took a while but I’m officially here for it. I’m a 90’s kid, so I was pumped when I saw FILA was bringing back this iconic sneaker.

Now, I know this trend is controversial, and part of me feels like a 90’s grandma (a chic one, of course), but it’s just such a fun trend to experiment with this season. There are so many ways to rock the chunky sneakers, keep on reading for inspiration on what to pair them with (& ultimately how to style Fila Disruptors)!chunky sneakers

biker shorts.

Sure, we’ll only be able to wear biker shorts for so much longer, BUT chunky sneakers & biker shorts are really the perfect match. I could have easily swapped my white sneakers here for my FILA Disruptors, and it would have instantly made my outfit more cool. I love biker shorts with long button down blouses, blazers and chunky sweaters (which is how I’ll be wearing them going into fall!).

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cropped pants.

Any cropped pants would work, really. Jeans, cords, khakis, trousers…all can be paired with the chunky sneaker, as long as they’re cropped at the ankle! Here, I paired it with a pair of cords I got on my Italy trip. I prefer the sneakers with wide leg pants vs. skinny or straight leg.

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pleated midi skirts.

I can’t WAIT to wear my pleated skirt again (in fact, it did make an appearance just last weekend). I think midi skirts with chunky sneakers is so edgy & fun. It’s feminine meets masculine, in the best way possible. If you’re feeling extra adventurous, you can wear the sneakers with a pair of glittery socks.

How will you be wearing your chunky sneakers this season? Tell me in the comments!

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This post is sponsored by FILA and Her Campus Media. All opinions are my own. Thank you for supporting the brands that make Cuddlepill possible!


  1. I haven’t hopped on the chunky sneakers train yet but SO many of my friends have and they are obsessed with theirs! Love the way you styled yours here!

    xoxo, Cecilia // sunnysidececilia.com

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