Skip to main content
how to style a midi skirt

Ask a Stylist Series: Style a Midi Skirt 3 Ways

It’s the day after Labor Day, which means we should stop referring to the weather as “summery” and start realizing that we are now having “unseasonably warm days.” Labor Day has always had a strange influence on our clothing choices (think: no white after Labor Day) and this time of year, people always seem to be confuses with “the rules” of fashion (NOTE: there are NOT rules, only guidelines!) So, starting today, we’re kicking off a new “Ask a Stylist” series to show off our favorites of fall fashion! We will help you dig through the trends you need to know about, and how to transition them into your current wardrobe. So, let’s get started!!

Ask a Stylist about Midi Skirts

Since I am at the boutique styling customers every day, I thought it would be only fitting to kick off the series myself! And of course, I’m talking about my favorite trend that many women are apprehensive to try; the midi skirt. Marie Claire says the midi is the only skirt worth wearing right now, and I wholeheartedly agree. It is as flattering as the skater skirt, but not as overwhelming as a maxi skirt; the midi skirt is the best piece to seamlessly transition your wardrobe from summer to fall, and from day to night.

Here are 3 Different Ways to Style a Midi Skirt:

To Work:

wear a black and white midi skirt black and white midi skirt to work

Midi skirts are conservative by nature due to their length usually hitting at or below the knee. This means it’s incredibly easy to keep it classy by throwing on a structured blazer and statement necklace. This is probably the most obvious way to style a midi skirt– you probably could have some up with this on your own! Actually, if you’ve been following along, we just wrote about styling a midi as part of your summer office attire.

To Dinner:

black and white pleated midi skirt black and white midi skirt


Your next girls night is right around the corner! Chicago is full of chic and trendy restaurants, and your outfit should match the environment. Pair a high waisted midi skirt with a crop top and balance chicness with sophistication. You may be familiar with a similar pairing: the skater skirt with a crop top. While the skater skirt is still a very popular style, the length in the midi skirt is definitely more on-trend than the mini, making the whole outfit look more refined and thoughtful.

Casual Weekend:

how to style a midi skirt how to style a midi skirt

This is probably the most unexpected, but definitely my favorite style of the three! Pair a midi skirt with a cool graphic tee, and you just completely transformed this look! Midi skirts can easily be styled for a casual weekend of shopping, running errands, or going to a lazy Sunday morning brunch with friends. There is nothing more exciting than finding a great piece that can be used from work, to play, to weekend, but the midi skirt has definitely proved itself to be just that piece.

Need more convincing that the midi skirt is the perfect summer-to-fall, day-to-night transition piece? Fellow Chicago blogger Jessica from Bows & Sequins had the exact same idea in her post today:

how to wear a midi skirt from summer to fall

How would you style your midi skirt for fall?

xo, Kristi

New to Welcome!!! I’m so happy you found us!  You may want to get to know us a little better here.
We update our blog weekly with style tips and lifestyle advice, so if you want more of what you just read, you should sign up here:



Related News

how to wear a blanket scarf

How To Wear A Blanket Scarf: Winter Edition!

How To Wear A Blanket Scarf: Winter Edition! January in Chicago means only one thing:...

3 Ways to Wear Jumpers this Fall

Ask a Stylist Series: 3 Ways to Wear a Jumpsuit for Fall

  3 Ways to Wear A Jumpsuit for Fall With fall in full swing, finding...

business casual work attire for fall

Hot Day, Cold Office: What to Wear at Work When It’s Hot as @$*k! Outside

Ok, this week was hot as $*&#! With all the weather we Chicagoans have been...

Leave a reply

Your email address will not be published. Required fields are marked *