How To Style: Dress Over Pants

Move over crop tops! As you may have noticed, this trend has been on the rise for the past couple of years following the resurgence of 90’s fashion. Though the notion of wearing a dress over pants seems a little tacky to some, it can actually look quite modern and elegant. Thanks to some futuristic heroines like Rey from Star Wars: The Force Awakens and Trinity from The Matrix, this look can really make me feel like a bonafide badass! This trend challenges you to rethink the way you wear the clothes that you already have! Let me help you get started!

Stylish Badassery a la Rey from Star Wars: The Force Awakens (left) and Trinity from The Matrix (right)

Proportions

As with most outfits, think of proportions. You want to balance your frame so you don’t look overwhelmed. To help you out, think of your silhouette. You don’t want both pieces to be overly billowy or skin tight. Your initial instincts will draw you towards wearing some leggings under a flowy dress. But perhaps consider wearing a tailored pant with a structured dress for a sleek look.

Here, I decided to pair a short frilly dress with some leather culottes. You could definitely rock this with a tailored pant. I just wanted to show that you don’t necessarily have to stick to a full-length pant. The frilly dress already has a lot of flowing volume, which is why I decided to go with a more structured bottom. Though culottes are wider than a typical pant, the rigid shape contrasts against the dress leaving you with an interesting silhouette.

Monochromatic

If you are a little confused where to even begin, I find that going monochomatic is a great starting point. It’s very easy to do black on black. You can also go with matchy matchy prints, which can be tricky to come by but look surprisingly put together rather than a hot mess! For beginners, try sticking to neutral colors first to make things easier. This creates a very clean, modern look.

I went with all black everything! This takes a lot of thought out of creating this type of look. I decided to go with pants with an interesting structure, with flared out pockets and a ruched, tapered leg (thinking of my silhouette again) and a long “dress” with really high side slits. You can also see how you can change this look by just adding a simple belt. I have worn this dress with leggings in the past, but I wanted to experiment and try something new out.

Layer

This trend is only going to get better as we transition into fall. Get your layering game strong as you pop on a jacket or cardigan that could either be longer or shorter than your dress. Either will work! If you have a sheer dress in your closet, this is the time to get the most wear out of it!

Here, I combined some girly pieces with more tomboyish ones. The bomber jacket adds another dimension to the flowy shirt dress cutting off ⅔ of the way down. And the relaxed ripped boyfriend jeans is juxtaposed with a dress which is more reserved preppy. Don't be afraid to throw some intensely contrasting pieces in the mix.

I took a sheer sleeveless shirt dress I had and wore it over some baggy high-waisted military pants and a fun army print bra. The baggy pants taper down the leg to keep it from looking too sloppy. Although the dress has a flowy A-line cut, the sheerness of it prevents it from looking shapeless and provides a fun peek-a-boo illusion with the printed bra. This sheer dress was difficult to wear on it's own so I am taking this opportunity to get more wear out of them!

Hemline

When a mini isn’t appropriate, it is an opportunity for you to try out this trend, even at the office. But playing with the hemline doesn’t mean you can only go short and long. Daringly high slits and asymmetrical hems are all fair game and add dimension to your look.  Remember those button-up shirt dresses that were in a couple seasons ago...unbutton the bottom half and you’ve got yourself an instant high slit.

I decided to go with a asymmetrical slit and wide leg pants. The dress is somewhat fitted on top so this creates a gradual a-line slope. The key to create a put-together look like this is to keep your pieces simple with subtle details. In this case, the subtle detail is the asymmetrical stitching on the waist drops to the hip and draws your eye to that slit.

Alternatives

So if you still don’t feel comfortable with jumping into the trend, you can definitely transition into it. Duster sweaters were big last fall and winter. You can start with that OR with a longer kimono. That will ease you into longer layers without seeming too “out there.” Longline t-shirts over jeans is another great starting point.

I took an extra long basic men’s shirt over a fun printed legging. This combo can ease you into this trend if you are a little uncomfortable going full out. Baggy tops over leggings were all the rage in the 90's.

Everything I am wearing here are items I have had for over a year. So whether you are on a budget or not, you can save some cash by just working with what you already have. Remember, despite what the industry says, fashion has NO rules the same way art doesn’t. It is only limited by your creativity and courage. Dress what makes YOU feel the best about yourself. The key here, as with everything else, is to experiment by giving new things a try.

Play fearlessly!