Trying to stay cool yet manifest autumn at the same time. Styling six vintage skirts including five maxi skirts.

As I’ve spent the pandemic decluttering the house including my closet, I’ve re-discovered some forgotten friends in the way of skirts. Styling skirts is a little bit daunting for me as opposed to say jeans. It requires a little more critical thought.

Styling these six outfits around vintage skirts was a useful exercise for me. It is beneficial to re-examine my clothing with fresh eyes once in a while and make decisions about what to keep and what to pass on. My tastes change. My body changes. Playing dress up in my closet always inspires new outfits; giving forgotten clothes a new day out, and conversely, passing things on that no longer work for me.

MONDAY

Mondays. Not my favorite. At the desk most of the day. The day was warm so I wore one of my favorite thrift shop finds. I found this vintage maxi skirt at Red, White, and Blue Thrift for $4 a couple of years ago. I love the ruffles! Wearing it here with a breezy vintage blouse and Puma sneakers.

TUESDAY

On Tuesday, I went to vote in the Connecticut Primary wearing this vintage maxi skirt, t-shirt, and Converse platforms. I bought this skirt on Etsy last year for $14. After spending several months looking at vintage peasant skirts, I settled on this one. I love the colors. There is enough black in the print, I can pretty much wear it with any black t-shirt.

WEDNESDAY

Out to run errands in a handmade skirt, one of my most cherished vintage pieces. It’s a thick cotton fabric with gorgeous metallic silver and green trim. Wearing it with Vans hi-tops and BCBG Max Azria green silk shirt.

THURSDAY

Fall is right around the corner. I can sense it as I gravitate toward autumnal clothing. I cannot remember where I picked up this pleated maxi skirt but it’s perfectly dressed down with All Saints boots. I’m not sure about the black necklace that I paired with this top from Zara. It’s somewhat unresolved.

A NOTE ABOUT SHAPEWEAR

Under all of these skirts, I wore shapewear and cannot sing its praises enough. They are comfortable! They hold you in and smooth away any bumps or ripples. I want seven.

My preferred choice is the Body Shaper from Uniqlo. I like the ribbed waistband for support and thinness of the fabric. $12.90 at Uniqlo.

These no longer have tags but I believe they are Uniqlo. They are comfortable enough to wear all day. $12.90 at Uniqlo.

Of the shapewear that I own, Spanx is the least comfortable because they’re also the tightest. It’s possible I have the wrong size. They do, however, really hold you in and carry some superb styles. Shop Spanx.

FRIDAY

Cooler weather and time to bring out another of my favorite finds. This 1970’s black and white maxi skirt was a score at a vintage clothing shop that I used to frequent in Las Vegas six or seven years ago. Sadly, it’s no longer in business. I love the construction and flow of this skirt. It is cut on the bias so it hugs the body yet it has some stretch to it. It shows every ripple so I was happy to have my shapewear on hand.

Wearing it here with a thin Neiman Marcus cashmere sweater and Topshop boots.

SATURDAY

Throwing it all the way back to the ’90s with this velvet Liz Claiborne maxi skirt, vintage tee, and vintage 1960’s Levi’s jean jacket. I didn’t buy this skirt second-hand. It’s one of a handful of clothing items that I have kept since the ’90s and is now cruising into vintage territory. I love its full length and richness of the black velvet. It’s a little hard to walk in as I’m a fast walker.

How often do you wear skirts? Let me know in the comments below.

More vintage styling on Mad Chipmunk