Lately, I feel like the trends coming down the pike are more like a speeding train that has gone off the rails and can’t be stopped.  I’m still refusing to embrace bootcut jeans because I’m still suffering from early 2000s draggy hem flashbacks, we’ve been dangerously teetering just a little too closely to the return of the shoulder for far too long, and dresses.  Would it kill someone to put a waist in one from time to time?  The recycling of fashion is hardly new, but living through the return of them can definitely be triggering.

Also being dug out of the yesteryear trunk are maxi skirts.  What’s my beef with them, you may be wondering?  Well, nothing really.  I’m actually pretty agnostic about their return.  Perhaps it’s because I’m at an age where I’ve taken multiple turns around the great big carousel of fashion and have way too much baggage about the return of any trend, especially when this time around I’m markedly older.  Objectively, there are plenty of great reasons that maxi skirts can be amazing.  They offer more range of movement, can hide a multitude of sins, and can even make shaving optional on the days you just can’t with the razor.  Maxi skirts are feminine, comfortable, and easy.

On the flip side, however, maxi skirts can look frumpy, can make a woman look squat, and camouflage body issues in a way that somehow makes them look worse.  In addition, skirts are, well, sort of a pain in the butt.  Instead of a dress, maxi, or any skirt, for that matter, requires additional thought.  Instead of throwing a dress on and being done, you need to find the right top that not just works with the skirt but works with your body.  Do we really want to cut our bodies in half with a waistband?  Do we really want the additional bandwidth it takes to figure out what top goes with your skirt?  This is why dresses are often heavily favored over skirts.

That said, there seems to be a seasonality to dresses and skirts and times that are skirt seasons and others that are dress seasons.  There have been times past when all everyone wore were skirts and dresses took a backseat, and vice versa.  Most recently, skirts barely registered because we were in a dress time.  Could it be that we’re entering into a skirt season, where dresses will take more of a backseat?  Time will tell.


Maxi skirts are most commonly worn for casual things because the swish and ease of them work perfectly for the things we do in our downtime.  For work, styling maxi skirts can be a little trickier.  In today’s post, I am putting five maxi skirts for work looks together using some styles that go beyond the swish and ease silhouette.


maxi skirts

Last year, I wrote this post about faking a dress by putting two matching pieces, a top and a skirt, to create the appearance of what looks like a dress but isn’t. This strategy is helpful for those who can’t wear dresses for a variety of reasons like having a short torso or very different top half to bottom half sizes. Despite being easy, dresses aren’t easy for everyone. So while this is a maxi-skirt look, it’s not exactly a maxi-skirt-looking outfit.

I styled this skirt from Max Mara Leisure with a matching top from the same brand. If you look at some maxi skirt looks for work out there, it’s hard to believe, but apparently, we’re dusting off the 80’s blazer with a maxi skirt look. You could do an easy blazer with a maxi skirt but, I warn you, this could go all sorts of wrong if you are petite, curvy, or both. I chose this shaped Veronica Beard blazer to create a little waist shape and bring the look into an easier proportion. I added this belt from Banana Republic to further create the illusion of this top and skirt being a dress, and finished the outfit with cognac flats from Margaux and a simple pendant from MM. Lafleur.


maxi skirts

In terms of maxi skirts, a tailored style is probably my personal favorite likely because it’s, not to be redundant, tailored. For some people, myself included in this group, swishy, easy is just not favorable over pieces that are more structured or tailored. This type of skirt meets that happy compromise of being a skirt but wearing like pants. Perfect for a change-up or a warm spring day.

I styled this black skirt from Vince with a black and white striped button-up shirt. I finished the look with red loafers from M.Gemi (I own these loafers in two colors and they are seriously divine), a white belt from Rag & Bone, and knocker earrings from Jenny Bird.


maxi skirts

So apparently we’re doing this, we’re doing denim maxi skirts. It’s not that I’m entirely against this trend, I’m just working on getting passed the Duggar 19 Kids and Counting vibe these skirts can invariably give off. But it can be done. The way I like to think of denim maxi skirts for work is to consider them jeans alternatives. Obviously, this won’t fly in a conservative work environment but in those where jeans are allowed, this style could be considered.

I styled this denim maxi skirt from Boden with a striped Breton tee from J.Crew and a red cardigan from Alex Mill that a client of mine loves so much that she also bought it in cobalt. For the casual work environment, I finished the look with Veja sneakers, huggie hoop earrings from Tuckernuck, and a white smartwatch band from Machete.


maxi skirts

This outfit should come with a warning label because easy over easy can be tough. The types of bodies a look like this works on are the types that typically don’t have a lot of lumps, bumps, or curves. They also tend to have enough height to mitigate how squat an outfit like this can make someone look. By bypassing the waist and natural hip curve, women with curves can often look boxy. This is why on models an outfit can be so alluring.

If I haven’t turned you off completely to a look like this, I styled this pleated maxi skirt from J.Crew with a Jenni Kayne cotton fisherman sweater. To add a little funk, I finished the look with these Office of Angela Scott brogues and simple small link drop earrings from ALLSAINTS.


maxi skirts

I like to call skirts like these standalone skirts because they’re skirts that have features that make them more than a basic. It makes styling them easier because they do a lot of the heavy lifting when creating a finished look. With this maxi skirt from Staud, I added this basic short-sleeved cashmere sweater from J.Crew and finished the outfit with black pumps, a chunky tortoise necklace, and a layered bracelet.