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I Just Decided I Hate My Entire Wardrobe, Now What?

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Where to start when you’re starting from scratch.

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Pictured is a cluttered walk-in closet. Photo: The Coveteur/Trunk Archive

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About a year ago, I found myself saying “I have literally nothing to wear” far too often for someone with a full closet. I wasn’t happy with anything I owned. (Whether it was because my style had changed, or my body, or if I was just being difficult, I’m still not sure.) So, I did what any reasonable person would do and got rid of it all.

My initial reaction was relief. I had made upwards of $100 at my local Buffalo Exchange (you can attest to this being a big deal if you’ve ever felt slighted while consigning), and was able to donate whatever they didn’t take to a local clothing drive. But with a clear head and closet aside, I started to settle into the reality of the situation. Now I actually literally had nothing to wear — once an exaggeration, now a fact.

For a week or so, I wore the same two outfits with subtle variations (thank you, layering), and thought long and hard about how to start all over.

Rebuilding your wardrobe — especially as an adult — can be a tedious and relatively expensive process, but when you go into it with a solid game plan, it doesn’t have to be a hard one. To take the guesswork out of how and where to start, you’ll find a handful of key pieces and suggestions below, straight from someone who's been there.

Your Live-In Denim: We’re always talking about denim here at Racked, and how could we not? Jeans are the truest wardrobe staple, regardless of how often that term gets tossed around. Invest in a pair that you feel totally comfortable in — for me, that’s one with a higher waist and straight leg — but regardless of silhouette and style, this is where I say splurge.

The Black Trouser: The black trouser has been my “business casual” shortcut for years. The style is typically made with materials that allow for a good amount of stretch and extra room that reads chic, not sloppy. The real sell here, though, is its versatility. Whether you complement with sneakers and a T-shirt or pumps and a silk blouse, you’re guaranteed comfort and a look just as good.

Versatile One-Piece: A one-piece outfit is an easy way to look like you tried a lot harder than you did. Jumpsuits are a great option, but if the whole bathroom struggle is too much of a turnoff, opt for the same idea in dress form. Either style will be a noticeable switch-up from the expected pants-and-shirt combo, with plenty of room to experiment with what you layer underneath.

Statement Shirting: Stocking up on a handful of your typical work-approved button-downs and blouses is a no-brainer, but adding in a few special pieces is a great and easy way to have some fun with your wardrobe (and keep your co-workers on their toes). This season offers plenty of choices, from added frills, pleats, off-the-shoulder styles, and more.

Cozy Sweater: A sweater that softens the blow of getting out of bed in the morning is crucial — because when you need it, you need it. Look for an option with a mock or collared neck to keep things polished when you’re feeling anything but.

Default Going-Out Top: The night-out uniform can be a challenging thing to establish. As someone who is generally always running about five minutes late to everything, it’s in my best interest to keep it simple; keeping an arsenal of easy-to-wear standout pieces is the best way to do that. Balance it out with jeans to keep the things casual, or elevate the look with a pair of trousers. (I told you, you’d need them both.)

Everyday Boot: These also get the splurge green light, because when you find the perfect boot, you’ll most likely put them to work for several seasons. To get your money’s worth, be sure to pick a pair with a heel height that you’ll feel comfortable in for hours on end.

The Casual Crossbody: What’s better than a dependable bag to pull everything together? The crossbody is the classic convenient choice, so you’ll find a version of it from almost every retailer and at every price point.