7 Outfit Formulas I'll Never Wear Again (and 7 I'm Wearing on Repeat)

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(Image credit: @elizagracehuber)

I've worn a lot of outfits in my lifetime and tried on even more. There are a few that I've worn some variation of hundreds of times and will probably continue to wear for decades to come. At the same time, there are many that, despite my trying to make them work countless times, just weren't worth a second go. That, or they were worn for years but simply no longer match my sense of style or the ways that fashion's evolved. The more outfits you wear, the more you learn about what you like—and in turn don't like. 

Since entering into the new year, I've really cracked down on those fashion combinations that just don't fit in with my style and/or current trends anymore, deciding to finally cut them off instead of holding out hope that they'll make their way back into my good graces. In total, I've narrowed down my eliminations to seven full outfits, from skirt and dress looks to denim ones. Scroll down to see which ones I'm on the outs with and which will remain in my rotation indefinitely. 

Out: Minidress + Blazer

In: Midi Dress + Blazer

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(Image credit: @elizagracehuber)

I used to enjoy the look of two hemlines matching up, but something about the idea that people could question whether or not I'm wearing pants with a blazer, especially if tights aren't involved, didn't age well in my head. The contrast of a midi dress or skirt with the same blazer, though, causes none of the same confusion. And if I want to make the combination even better, I'll pair black with navy, a duo that looks elegant every single time.

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Out: Short Denim Skirt + Knee-High Boots

In: Midi Denim Skirt + Knee-High Boots

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(Image credit: @elizagracehuber)

The resurgence of Y2K trends had me thinking there for a second that I wanted to wear denim miniskirts with tall boots à la Nicole Richie or Paris Hilton back in the day. And while I love an archival outfit photo from the aughts just as much as anyone else born in the '90s, I don't need my closet to reflect that. My preferred take on denim skirts and boots is far more anti-trend: a long, black denim skirt styled with knee-high stiletto boots. It's a bit more tame but still fun because of the high slit in most midi-length jean skirts. 

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Out: Oversize Top + Skinny Pants

In: Fitted Top + Baggy Pants

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(Image credit: @elizagracehuber)

Growing up, one of *the* most popular outfit formulas was skinny pants, usually jeans, with an oversize, billowy top. It was practically all I wore in high school and early on in college. Luckily, I've moved on from that time in my life and learned a thing or two, which is why I traded in that combo for the opposite one: oversize, baggy pants with a fitted top. 

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Out: Vintage Jeans Tucked Into Tall Boots

In: Vintage Jeans With Kitten Heels

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(Image credit: @elizagracehuber)

It's not that I've never seen someone make tucking jeans into tall boots look good. I have (the obvious one being Princess Diana). But it's simply never worked for me. I've tried and I've failed and as a result found that kitten heels are a far better companion for my vintage jeans than tall boots ever will be. Plus, with a tiny-heeled pump or mule, some of that Western kitch factor that isn't always the vibe disappears.

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Out: Statement Matching Sets

In: Minimalist Coat + Statement Skirt

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(Image credit: @elizagracehuber)

Maximalism had its time in the sun, with clashing prints and allover color reigning supreme on the streets and runways alike. But I, for one, far prefer the aesthetic's opponent in minimalism (with a touch of excitement, of course). That's why, rather than wearing a full statement matching set like I could have with this Lafayette 148 skirt (which does have a matching coat that I equally adore), I paired it with a simple white tank and black maxi coat. I'd do the same thing if I owned the silver coat—that is, pair it with jeans and a tee or a black midi skirt and tank top. 

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Out: Sweater + Maxi Slip Skirt

In: Sweater + Knee-Length A-Line Skirt

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(Image credit: @elizagracehuber)

There was a time when all I wanted to wear was a floor-length slip skirt and a sweater. It was all over my Pinterest feed and therefore felt like the epitome of chic. But I've found of late that a too-long slip skirt can tend to make an outfit feel overly formal, whereas a knee- or midi-length skirt like this A-line one keeps the elegance factor while maintaining a level of daytime casualness. It's the perfect compromise.

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Out: Allover Saturated Hues

In: All Black With One Colorful Accessory 

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(Image credit: @elizagracehuber)

Trust me, I've tried to pull off the allover-color look from the days when dopamine dressing was all the rage, but it just never clicked with my personal style. Instead, I've found that styling one brightly colored accessory, usually a handbag or pair of shoes, with an otherwise all-black outfit is my sweet spot. 

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Senior Fashion Editor

Eliza Huber is a New York City–based fashion editor who specializes in trend reporting, brand discovery, and celebrity style. She joined Who What Wear in 2021 after almost four years on the fashion editorial team at Refinery29, the job she took after graduating with a marketing degree from the University of Iowa. She has since launched two monthly columns, Let's Get a Room and Ways to Wear; profiled the likes of Dakota Fanning, Diane Kruger, Katie Holmes, and Sabrina Carpenter for WWW's monthly cover features; and reported on everything from the relationship between Formula One and fashion to the top trends from fashion month, season after season. Eliza now lives on the Upper West Side and spends her free time researching F1 fashion imagery for her side Instagram accounts @thepinnacleoffashion and @f1paddockfits, running in Central Park, and scouring eBay for '90s Prada and '80s Yves Saint Laurent.