What constitutes a fashion “rule”? Never wear white after labor day? Don’t wear double denim? Certainly don’t pair blue and black together! Excuse me, but please. Who is making these rules and why are we so scared to break them? Come to think of it, why are there rules? Do your thing, especially when it comes to what you put on in the morning.

I love this sentiment but, admittedly, I’m pretty conservative when it comes to what I wear. I try to be focused on style over trend; only adding a few key pieces that can be sustained over time, although I think it has more to do with not wanting to over think getting dressed. All that said, I also want to be true to myself and have a little fun. It’s fashion. Why not take a risk? What’s the worst thing that could happen aside from someone saying you look a bit like Steve Urkel? And if you’re really going against the grain, maybe you like portraying a little Urkel in your sock selection.

It’s fall, and I’ve seen plaid everywhere and I was inspired to experiment with the Adam Lippes for Target collection and satisfy both my conservative “a few key pieces to add to the wardrobe” side and my fun “what the hell, wear them all at the same time {mic drop}” side.

I have been on an ongoing quest to determine the quintessential “Kate Arends” style. In this style journey, I’m challenging myself to branch out from my simple, classic basics, maybe break a few rules.

With both sides satisfied, I determined I do have one hard and fast fashion rule: be true to yourself.

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Thanks to Target Style for the inspiration.

Break the Rules: Women’s Classic Ankle Pant Black/White – Merona // Women’s Revel Asher Flats // Women’s Crew Socks – Merona  // Kate Spade Saturday pullover (N/A) // Buffalo Plaid Jacket (similar)

Follow the Rules: Adam Lippes for Target Shirt Dress – Painterly Plaid Black // Alexander Wang booties (similar) // Szeki 7115 Wool Coat // Madewell Sweater Vest (similar)

This post is brought to you by Target Style. Shop the new Apparel & Accessories collection in stores and online.

Kate Arends

Kate is the founder of Wit & Delight. She is currently learning how to play tennis and is forever testing the boundaries of her creative muscle. Follow her on Instagram at @witanddelight_.