For a couple of years now it has been one of my style goals to wear dresses more frequently. I’ve had some success after finding the right dresses and the right footwear to complement them. I get more versatility out of dresses by sometimes wearing them over cropped flares or straights to create a tunic look. 

Initially I struggled to find the right dresses, and you’ve probably heard my complaints about lengths that are too short, lack of sleeves and flimsy fabric. But recently that’s turned around and I have doubled the size of my frock capsule in a short space of time.

I like to keep my wardrobe to a moderate size, so as I added new dresses I also needed to do some editing. In this post I’d like to take you through my thought process.

Dresses I Passed On

I am done with sack dresses because I don’t want to wear oversized looks anymore. I therefore passed on a voluminous navy flag dress, which creased a little more than I could handle. I continue to enjoy fluid shirt dresses without waist definition, but passed on the denim and striped linen ones here because they were worn out, torn under the arms, and lost their luster. I passed on the Ann Taylor printed sweater dress because the neckline stretched out, which made it lack structure where I need it most — adding width to my narrow shoulder line.

Dresses in the Holding Zone

I am moving away from classic sheath dresses. They create conventionally flattering proportions, but it’s not the silhouette I want and I’m not comfortable wearing them. Both of these older dresses fit well, but I’m putting them in the holding zone. The turquoise sleeveless sheath is sentimental because I wore it for my 40th eight years ago. The sleeved sheath has a matching tweed jacket which is a fun timeless suited look I might want to revisit.

Dresses I Recently Added

I added eleven dresses to my wardrobe over the last ten months. It’s a lot, since I only edited out six. But I have very few skirts (one casual, two dressy, and one in the holding zone) and the space to store five extra dresses so it’s worked out.

All lengths are knee and midi, and in silhouettes that I am comfortable wearing on this leg of my style journey. I want to wear structured dresses with romantic movement, but not too structured and not too much movement. This leaves me with shirt dresses, A-line shifts, fit-and-flare styles, and some sweater dresses. For the most part, this is what I have added.

I LOVE my new dresses. The asymmetrical olive shirt dress from COS is voluminous but is very structured on the shoulders and sleeves, making all the difference. The patterned red poppy dress is a sheath, but it isn’t tight and the balloon sleeves blew me away.

Current Dress Capsule

I now have seventeen dresses across an assortment of colours, seasons, patterns and dress codes. I have a dress for every occasion, except a fancy formal ball. Some of the dresses are very dressy, and reserved for formal functions. But the rest I wear daily to work with clients, out and about, or out to dinner. I’ll pop a denim jacket or gilet over the top to dress them down. I wear some as tunics over cropped straights or flares. I pair them with flats, sneakers, low-heeled booties or tall dressy boots. I reserve the low-heeled pumps for formal occasions. In Winter I combine the heavier weight frocks with hose, tall boots, a thermal tee, coat and scarf.

I have waited a long time to have a closet full of dresses in the silhouettes and colours that tickle my fancy, and I am absolutely delighted. The only thing left to do is wear the heck out of them.