How to Style a Skirt Two Ways

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Whenever I’m shopping, I like to make sure that my clothes fall into the happy middle ground of being wearable for work, but with a few tweaks, could go a completely different way. It can be a hard thing to pull off though. It sometimes leaves you wondering if your top is a bit too casual or if maybe you should have cooled it on the heels. The line can be treacherous. But, I’ve discovered the best clothing piece that can go both ways: the skirt!

Why is a skirt the easiest piece to style two ways?

Sometimes skirts feel like the most versatile pieces out there. They can vary in length and shape, color and pattern. Yet, so many of them can be work appropriate! On top of that, you can pair skirts with everything. Case in point: in college, there would be days when we would have to wear our sorority shirts around campus. Yes, I could have paired the boxy large shirt with a pair of jeans, but instead, I tucked that shirt into the cutest skater skirt I had. Instant upgrade and I was still super comfortable. Plus, I could have done that with any skirt I had laying around.

Also, can you choose to make your skirt the focus or the ground piece. For example, in this post, my skirt was the focal point because of my white shirt. But in this post, my skirt helped my body suit stand out a little more.

J.Crew Factory Skirt
Everlane Tank c/o
Everlane The Day Heel c/o
Kendra Scott Necklace

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J.Crew Factory Skirt
Everlane Tank c/o
Everlane The Day Heel c/o
Kendra Scott Necklace

How to style a skirt two ways

First, pick your occasions

Figure out where you’re going to wear your skirt to. This can be for multiple places if you want to see how versatile your skirt is. Or you can just focus on styling your skirt for one event for now. Are you wearing it to one dinner? Are you wearing the skirt to work? Maybe you have a party you want to wear it to. Either way, know your event and dress for it. If you’re going to work, save the crop top for your party.

Decide on if it’s going to be the focal point.

Do you want everyone to focus in on your skirt? Then pair it with neutrals and basics. Neutral colored tops with simple designs and shoes that aren’t attention grabbing. A simple heel or a basic flat. If you want your skirt to be the background piece, then make sure whatever you’re going to pair it with stands out. Aim for contrasting colors, that still compliment each other. The easiest way to do this is to look at a color wheel and see what colors are on opposite sides of each other. Those are complimenting but contrasting colors. Make sure that whatever other pieces are part of your look are simple and not attention grabbing.

Accessorize

Jewelry, bags, and jackets, it’s your chance to go crazy….or not. Your call. Remember, this all goes back to your focal point. Where do you want the attention to be? If you’re keeping things simple, dainty jewelry is the best way to go. When you want to go all out, I love statement pieces, but I try to stick to one really good statement piece. If when you’re done you look in the mirror and you feel like you have too much on, just take off the last piece you put on, then leave your house. No regrets here people.

Important things to keep in mind when you style a skirt two ways

Shoes

Shoes can really make or break an outfit here. again, you have to know where you’re going and what would be appropriate. Are you going to wear your highest stilettos to the office? Probably not. Would you want to wear them to a nicer dinner? Maybe. If you’re not exactly sure how to judge the height of your heels, I say that heels go on a sliding scale: the longer your skirt, the higher your heels can be. The shorter your skirt, the flatter your shoes. Please note the CAN BE part of that statement though. You don’t NEED to wear heels just because you’re wearing a maxi skirt. You do you my friend.

Pair with Like or Contrasting Pieces

When I’m at work, I prefer to pair like pieces with like pieces. For example, this basic tank (and probably a cardigan) with my midi skirt. But when I’m dressing for fun, I like pairing more contrasting pieces. I’ll pair a crop top with a midi skirt or a pair of high waist jeans with an open back sweater. It’s all about balance and making sure you know where to draw the line.

As long as you know where the line is, then deciding how to style a skirt two ways can be incredibly fun. Plus, it can double the size of your wardrobe.  What do you think? Do you like to keep your work wardrobe separate from your weekend wear?

Photos by Kimberly Graydon