Best & Worst Outfit Choices

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

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. 

Favorite Outfits

One Third Jacket 01

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.

Cuyana Scarf

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.

Madewell Eyelet Top

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!

m gemi sandals, chloe bag, summer style

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. 

Navy J Crew Regent Blazer, Grey Stuart Weitzman Highland Boots

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. 

Black Midi Dress, Pregnancy Style, Maternity Outfit, Summer Style

Original Post // Black Midi Dress

One of two maternity outfits on this list. I still own and wear this non-maternity dress. 

Plaid J Crew Shirt, Plaid Asos Scarf, Sam Edelman Petty Boots

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).

Grey dress and ivory coat at 26 weeks pregnant

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. :)

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