My Worst Outfits of 2018

Each morning I’ve gotten into the habit of taking a quick outfit photo and posting it to Instagram.

I like doing this for a few reasons.

#1: It helps me see what I’m wearing and NOT wearing. This helps me when it’s time to purge my closet, AND when I’m considering purchasing something new (or new-to-me).

#2: I frequently give presentations and have work events where I see the same group of students throughout the year. I like to mix it up a bit and not accidentally wear the same exact dress every single time.

#3: When I’m lazy, I’ll just look through my Instagram and recreate an outfit I wore and liked.

#4: I like to look every so often to see what worked and what didn’t work.

Often, this helps me fine-tune my style and lean toward the outfits that make me feel confident and happy. After wearing something and NOT loving it, it’s much easier to list the item for sale or donate it. I don’t need that negativity in my life!

I just did a little review of my 2018 OOTD folder and thought it would be interesting to share my WORST outfits, why they suck, and how they can be fixed.

Worst Outfit #1: January 11, 2018

Okay, this outfit isn’t totally TERRIBLE but it’s not great either. I went with a black top, black sweater, black pants and silver shoes. I’m not against wearing all (or mostly) black, but this just doesn’t look great on me. It’s boring. The flowy top melds into the sweater, so my whole middle looks kind of like a blob.

Room for Improvement: So, how could I have made this better? Well, a brighter statement shoe could have helped. Also, I could have switched out the black cardigan with one that was more interesting. And of course, I could add in some color.

Here are some similar outfits I wore in 2018 that worked much better:

Each of these outfits has the same formula of slim pants + flowy blouse + cardigan. However, they also include a bit of fun… whether it be the colorful tank top, or the patterned cardigans with colorful shoes.

Worst Outfit #2: April 17, 2018

The oversized cardigan has its time and place, but for this office look… it is just too much. The proportions are totally off and I look frumpy. When it’s cold outside, who DOESN’T want to wear their pajamas to work? In hindsight, I could have done much better.

Room for Improvement: As you can see, this is the same basic outfit formula as my first example outfits. In fact, it’s using the exact same shirt and pants as one of the ‘better’ outfits. It’s the cardigan that needs to be replaced with one that is much more flattering, but still comfortable.

 Here are some similar outfits I wore in 2018 that worked much better:

For the first two options, we still have the same three pieces: cardigan + top + pants. However, the cardigan is less HUGE, so the whole look works much better. The second cardigan is actually a bit oversized,but it’s length is less sloppy. For the third look, I embraced an oversized sweater but kept the look flattering by doing a little tuck in the front to give it some shape.

 Worst Outfit #3: January 18, 2018

I went with a light grey, dark gray and black look… and it is frankly kind of awful. I think the shoes take it from just ‘ick’ to full-on ‘NOPE’. In this case, a statement shoe is not working for me.

Room for Improvement: If I would have switched to black booties, this outfit would have still been boring, but not as terrible. The sweater doesn’t look that great on me either(which is why it has since been donated back to the thrift store).

Here are some similar outfits I wore in 2018 that worked much better:

As you can see, I’ve revisited the skirt + tucked-in shirt formula many times this year. By keeping the shoes consistent with the color on the lower half, it helps the whole look feel a lot more professional. Where I did use a ‘pop of color’ in the shoe, it was a pointed flat rather than a somewhat country-feeling bootie. The color blocking of gray’s in the first look wasn’t doing it for me… but by adding in patterns you can see that not only is the look a lot more flattering, but I’m much happier too!

I’m sure I will continue to have plenty of ‘worst’ outfits in the future, but by taking a look back at what makes me feel/look good and what doesn’t, I can continue to fine-tune my closet and my style.

Did you find this exercise helpful?