While we thoroughly appreciate the joys of getting dressed, we understand the process is not always without conundrum. Fortunately, styling and getting dressed is our bread and butter so we come bearing solutions.

The Conundrum

Just how does one pull off wearing a dress over jeans?

Though the dress-over-jeans look had some questionable moments in early aughts, the trend resurfaced circa 2018 among the street style set in a sleek and edgy way that is here to stay. Dresses are an outfit on their own, but wearing them over jeans adds a fashion edge and another layer onto an otherwise simple outfit. Not to mention it’s an incredibly practical way to extend the wear of your dresses. 

Cool as the look may be, it can be an intimidating trend to try. Ease into it with our guidance below, plus a few looks to inspire you.

The Adios Dress paired with cut-off denim jeans, red boots, and a classic blazer

The Solution 

Start off with skinny or simple straight cut jeans, ideally with a raw edge. This provides a nice balance and juxtaposition to the more feminine dress that looks intentional with just enough edge. I find knee-length dresses and longer look best. Asymmetrical styles, and shirt dresses with the bottom half unbuttoned also work great. 

Photo by Nikkifreestyle.com

You can experiment with different shoe styles; we’re particularly fond of feminine flats and ankle boots. Lastly, stick with dresses in lightweight materials. 

The Adios Dress layered with a white turtleneck and paired with white ankle boots.

Photo by vogue.com