Looking Posh for a Night Out in 2025 Means Wearing This '90s Shirt Trend and Heel Trend With a Miniskirt

Now that it's mid-September, chances are your fall social calendar is filling up, and you're going to need after-dark outfits. While jeans and a nice top is a pretty foolproof combination, there are going-out outfits that are more posh, and Chase Sui Wonders just put one on display. For a Chanel dinner in NYC this week, Wonders opted for an all-black outfit that would've looked as chic in the '90s as it does in 2025.

As someone who loves a miniskirt outfit this time of year and is as invested in '90s style as every other fashion person, I was really intrigued by Wonders's outfit. With her leather miniskirt, she wore a shirt trend that was everywhere during the decade, along with a shoe trend that Chanel made famous. I'm referring to a silk button-down shirt and slingback block-heel shoes (yes, the cap-toe ones). The beauty of this posh going-out outfit is that it's quite simple to put together, and you might even have similar pieces in your closet already.

For an even more night out–friendly look, do as Wonders did and button just a few buttons in the center of the shirt. Keep scrolling to see what I mean and shop similar pieces to re-create her '90s-inspired outfit.

On Chase Sui Wonders: Chanel bag and shoes

Shop Silk Button-Downs

Shop Miniskirts

Shop Block-Heel Slingbacks