I have this uber comfy gray jersey maxi skirt that I love to wear. It’s so comfortable that I could literally wear it every day. It’s also surprisingly flattering. But instead of wearing it out of the house for anything other than errands, I keep it locked up with a baggy sweatshirt or coffee stained t-shirt and big socks. I don’t think I’m giving that skirt the proper airtime!

So…for my first column where I take 1 piece and do it up 5 ways to create completely different looks, I’m going to get imaginative with one of my favorite items of casual wear. I’m even going to attempt to dress it up. Let’s do this.

Way One: Funky Casual

This skirt is dying for a pair of slouchy boots, off the shoulder sweater and some generally funky accessories. This is the way that I usually wear it (complete with the collar and long necklace). It feels slightly more dressed up than a sweatshirt.

Pieces shown:

Pop Colour Shirt Collar in Red: $25 Simons.ca 

Sparkle & Fade Crop Seamed Mesh Sweater: $54 UrbanOutfitters

Women’s Journee Collection Faux Suede Slouchy Ankle Boots: $43 Target

Opera Pearl Necklace: $30 JewelMint

Way Two: Flower Power

There is nothing like taking the most basic piece in the world and then adding a current trend to it to really liven it up. Floral and a flat grey actually go together quite nicely if you do it right. In this case, I used a peplum top, but you could also crop it up with floral like the below look.

Pieces shown:

Tra La La Bustier: $65 Modcloth

Vintage Western Denim Jacket: $68 ASOS

Vidoretta Jamie Neutral Espadrilles with Ankle Wrap: $89 Zappos

Belle Eco Clutch in Blue: $193 Lion’esque Style

Way Three: Boho Rocker

Who ever said jersey doesn’t equal rockstar? Bah. I think it does. I just think you need to accessorize it up to make it so. In this case, I was seriously inspired by a stock image on Shutterstock of a very hip looking woman who looked like she had just got off tour with the Rolling Stones.

Pieces shown:

Ivory Bohemian See Thru Flowy Hippie Tunic Blouse: $30 Market Publique

Impressive Black Wide Belt / Corset Look: $29 Uniqua Studio on Etsy

Rivingtn Leopard Ankle Booties by Steve Madden: $149 Piperlime

Luxe Rachel Zoe Wool Floppy Hat with Buckle: $28 QVC

Way Four: Crop it Up

This look is quite similar to the floral one. But the difference here is that you will be bearing belly! My skirt is high waisted, which makes me feel WAY more comfortable about this look. But if you have a 6 pack of abs, feel free to bare it all. I’m jealous! My favorite piece here is the necklace. I’m dying to find an occasion to buy this one for.

Pieces shown:

Lace Corset Style Crop Top: $22 TopShop

Rainbow Thread Necklace (man I love this. So unique): $480 Moda Operandi

Levi’s Trucker Vest: $68 Piperlime

Women’s Rory Cork Wedge Sandals: $30 Payless

Way Five: Going Glam

Alright. I showed you that with the right pieces, you can rock out a grey jersey skirt. Now I’m going to show you how to make it look like a formal long skirt. Ready?

First off, you need to add textures to the other pieces that bring up the overall glamour of the outfit. Satin. Bling. Another option than what I am showing is to pair a sparkly tank with the skirt and silver strappy heels. But I went with a warmer version as it is still a bit nippy at night.

Pieces shown:

Cropped Tuxedo Blazer: $19 Forever21

Lauren by Ralph Lauren Mandell Ruffle Broadcloth Blouse: $80 Dillards

Tony Sandal by Michael Kors: $175 Zappos

Diamond Cascades Earrings: $168 BaubleBar

Whew! That was fun. Now I can live in that skirt. That makes me happy.