I’ve been documenting my outfits on here for seven years. I thought it would be fun to round up my favorite outfits and the ones I regret.
As I was looking through past posts, there were plenty of outfits that I didn’t love but I’d wear a version of them now.
There were a few that I regret as they are so far from my style that I cringed when I came across them. It should come as no surprise that 3 of the outfits have more color that I typically wear. I guess I had a real love of the color mint at some point in the past?? Let’s jump right into my worst outfit choices of the past 7 years.
Worst Outfit Choices
Original Post // White Out
While I like the dress and still have the mug and hat, this outfit together is one big mess of trying way too hard.
Original Post // Cotton Candy
What in the world was I thinking??! There are way too many colors going on here. Leopard shoes, hot pink bag, and blue sweater? I can’t even tell what color the jeans were. Probably mint. I do recall that scarf was very cozy.
Original Post // Chambray & Mint
The single reason this outfit makes me cringe is the sandals. I don’t know when it happened, but I cannot wear such dainty, barely there shoes on my feet. I think it makes them look fat.
Original Post // Farmer’s Market
Jim said I actually wore these pants a lot. Fortunately I have no memory of it.
Original Post // My Favorite Statement Jacket
My love for this jacket from One/Third is well documented. I only wish I had an excuse to wear it more often.
Original Post // Travel Style
This outfit is my true every day style. Sometimes I switch out the loafers for sneakers. I wear this once a week, at a minimum, in the fall and winter.
Original Post // Eyelet Top
I bought this jacket five years ago from Banana Republic on a whim. I definitely feel a bit “extra” when I wear it. This winter I am vowing to wear it with my everyday outfits. No need to save it for special occasions!
Original Post // Take Me to the Disco
I cannot quite put my finger on the reason I like this outfit so much. It’s pretty plain – a white tee, jeans and grey handbag. I don’t even know if I’ve ever worn the shoes out of the house, but they’ve made it through 3 moves and numerous purges.
Original Post // Navy Blazer
One theme from this list is my love of jeans and a good blazer. Five years later, J. Crew still sells this blazer so you know it’s a good one.
Original Post // Black Midi Dress
One of two maternity outfits on this list. I still own and wear this non-maternity dress.
Original Post // Plaid on Plaid
By now you know I don’t wear a lot of patterns. Somehow I managed to wear two different plaid patterns on top of each other in a way that I like to think actually worked. I wish Asos would bring back this plaid blanket scarf. It’s perfect for traveling (you know, when we can safely start traveling again).
Original Post // Shades of Grey
I wore this outfit for Christmas Eve when I was pregnant with Lawson. I remember feeling very confident in how I looked and felt at the time. I believe that was the first Christmas Jim and I spent together.
Original Post // Playing in the Rain
Okay, I don’t even know if it was actually raining that day. After I had kids, I didn’t feel comfortable in these types of shirts anymore. I miss this one though.
Original Post // Black and Grey
I LOVE this outfit. I recently gave away that shirt and looking at this photo kind of wish I had kept it. I definitely wish I still had the jacket. Pretty sure I gave it away when we moved to California. Had I known we’d then move to Colorado, I probably would have kept it. Now I want to search Zara for something similar. :)