3 Skirt Lengths 3 Different Styles

Does it even feel real that fall is here? If you were to have asked me that question before this post’s thrift haul, I would have answered no, but there really was something therapeutic about picking out wools and plaids that got me excited for the most wonderful time of year (Halloween and Thanksgiving)!

If you’ve read my other blog posts you should know by now that I always go into Goodwill with a plan. Sometimes that plan deviates but for the most part, it keeps me focused on what to look for. My plan for this trip was fairly loose, but it revolved around the only good thing this quarantine has provided me. Not having to wear real pants! I love spending the fall in dresses and skirts paired with cute boots, socks, and light jackets. It’s the perfect temperature to show a little skin while also getting to accessorize to a T. So for this post I wanted to show you how I styled a short, midi, and long skirt all found at Goodwill! Follow along with me as I style these 3 skirts lengths, 3 different ways.

Short Skirt Length

Short Skirt Length
Black boots and long socks

The first skirt I found was actually part of a suit set! Always try and hit every section of the Goodwill racks, I have found so many gems this way and this trip was no different. I did a little bit of editing to these clothes that took me all of a few minutes. For one, I cut the shoulder pads out of the sweater. I know shoulder pads are trying to make a comeback but for me, I’m just not ready. I also pinned the skirt at the seams to make it into a mini skirt length (originally it fell just below the knee). I could have taken my sewing machine to it, but I love the skirt at both lengths, so I like having that option in the future. I wanted to pair this skirt with a bright solid color, so when I found this green shirt with the scalloped neckline for ONE DOLLAR, I knew it was meant to be. For all you Halloween costume searchers, I also get big Heathers (1988) vibes from this outfit. Grab a croquet mallet and you are set.

This outfit was finished off with a pair of knee-high socks, handmade earrings, and…. THESE SHOES! These booties made my heart sing. This past spring I finally had to retire my most favorite booties of all time. They were the classic 1990s chunky buckle shoes that made you feel like a total baddie wearing them. I searched high and low to find those exact shoes again, even took them to a cobbler to see if they could be saved, but a resounding no was all I was given. But then, yesterday, cue flying angels and harp playing these boots were just sitting there in my size just waiting to be worn by my feet. Dramatic? Maybe a little, but I seriously could not contain my joy.

Midi Skirt Length

Midi Skirt Length
Brown booties

My second outfit features a retro-inspired midi skirt from the LOFT, which was also only one dollar! Another tip I have for goodwill searching is check areas in the racks that are not your size. I found this skirt in the larges and it was 4. Sometimes when shoppers second guess their picks, they just put back their treasures anywhere on the rack. I loved this skirt because I am so obsessed with that 1970’s brown, burnt orange, and yellow look. I paired this outfit with another pair of boots that I found on this trip (how lucky am I?) and ruffled boot socks. Last but not least this J. Crew blouse. This color and style are so on trend right now that I was shocked this gem wasn’t already picked up!

Long Skirt Length

My last outfit features a vintage long wool skirt. I love this skirt for fall because it cuts right at the perfect length to showcase my cute booties and with the longer length allows me to wear a more risqué top (well risqué for me at least). This skirt length and material could also transition beautifully into the winter seasons as well, just pair with a higher boot! The shirt from this look was thrifted at Goodwill about two years ago and it is still a go-to for me.

Styled Long Skirt Length

So there you have it! Three skirt lengths, three different styles. I know it can be hard to go against your comfort zone with skirt lengths, but challenge yourself this fall! I needed this fun exploration of my style in a time when sweatpants is the #1 most worn item in my closet right now. Even if I only wear these outfits to the grocery store, it felt like I had a little bit of my identity back. I’d love to see how you style your thrifted skirts, so please send some pictures to @goodwillgoodskills -Happy thrifting!