Monday Musings on Outfit Failures
Happy Monday, ladies. This week, I’m reflecting on some recent outfit failures. I know I’m not the only one who regrets clothing combinations, and I thought you might get a kick out of seeing a few of mine.
Color
Our weekend was chock full of holiday activities that required festive attire. For my first luncheon, I chose to wear the one-and-only red sweater I own. Eileen Fisher called it Azalea, but it’s red on me.

I bought this on sale last year thinking…”it’s in my color palette, so I should be able to wear it confidently”. Not a chance! I was uncomfortable and hated every second I had it on my body. It didn’t look bad on me, but I hated how I felt in it. We did not take a photo of what I was wearing because I was in a rush to get home and change. Personal color palettes are intended to help us wear colors that flatter our complexions, but if you don’t feel great in a specific color…skip it!
It’s now folded and ready to be added to my donation bag. I considered hanging it back up and waiting until next Christmas to see if I felt differently, but I don’t think that makes sense. I’ve worn it twice in 12 months and felt uncomfortable both times, so the chances of me changing my feelings are slim. I’m grateful I got it on sale.
Color with Fabric
My next failure was when we went out to dinner and saw The Nutcracker.

I’ve been wanting a tulle skirt for years and thought wearing one to the ballet would be fun. I really, really wanted a black one, but I talked myself into this gray. It’s in my palette, and I’ve been trying to avoid wearing so much black.
I ordered three pairs of gray tights, but neither was the correct shade. Since the skirt was long, I went bare-legged with my gray ballet flats (no longer in gray). I loved the way I felt wearing this skirt, but I hated how it looked. Tulle, by its very nature, is a feminine fabric that’s a bit outside of my comfort zone. I would have preferred the seriousness that the color black would have given the tulle and I could have worn it with my black suede booties.
Accessories Overload

Mercifully, this outfit never saw the light of day other than to capture this photo. I was experimenting with how to wear my new wine red cardigan and added way too many details. I can happily wear this red, but not with all the other distractions.
A plain black sweater would have suited me better with my faux leather pants. The shine of these booties is also too much with the pants, and the color is distracting. Black suede booties would have been preferable because they lack shine and would have visually receded. I’d likey skip the black poof brooch as well.
I like to walk the line between minimalistic and accessorized so too many details feel heavy and overdone on me.
Care to share any of your latest outfit fails?

“because my life is so casual and my preferred esthetic is not.”
You just stated my struggles with fashion beautifully! Thanks for being real with your readers. You’re a treasure, Jennifer.
Happy holidays!
Linda
Thanks for being here Linda! I want to explore that further in 2025.
I actually love the azalea color on you. I just think it’s a lot of color so close to your face because of the high neck and boxy shape of that particular sweater.
My favorite art teacher used to say, “ if you aren’t making mistakes, you aren’t learning “ .
The most famous artists are often only known for a few works , not their whole body of work.
Smart thought, to keep in mind..
Thank you for taking the time to discuss outfits that miss the mark. I like the gray tulle skirt, but gray is one of my favorites and looks good on me. It’s all about what looks good on you in your own eyes. I can see that outfit #3 was just a little too shiny. I think it was the plaid blouse. Leather/pleather pants are always tricky, I think. My fails are usually in items I sew for myself. Even when I have taken the time to tailor blazers, they sometimes don’t work. However, after spending the time and the money to make an item, if I don’t love it, I usually put it away for a while. It turns out that sometimes I am just a little too close to it to see that it is probably OK. One thing I have learned, bargain fabrics don’t make great clothes no matter how well they fit. I guess we all already know that, but cheap fabric can be tempting.
I made that mistake often when making my own clothes, too. It’s doubly painful when you’ve spent the time making it!
Hi Jennifer,
Have you considered dying the grey skirt black? If you like the material, why not make it the color you like? YouTube probably can give you some suggestions on how to do it.
Enjoy the rest of your day!
Thanks Carolyn!
Red looks good on both of us with the same coloring and palette. But I have never ever liked red. I feel the same about orange and could never wear that Broncos sweatshirt even with a blue shirt underneath. We have to personally feel comfortable in our clothes, both the color and the size and style. I love tulle but would not look good in it as I am 5’1” and a little curvier than you. Skirts haven’t looked good on me since high school when I was a skinny 106 lbs. Now at 137-138 I need a larger waistband and all the sizing now is ten inch less than hips. Ugh! I’m five inches so things are baggy in the hips when they fit my waist. Like you Jennifer, I must feel comfortable in color and fit. I refuse to suffer for fashion.
Kudos to you for sharing outfit bloopers! Very amusing, humanizing, and informative!
I’m glad you liked this 🙂
Hi Jennifer! Where do you donate your clothes? Do you ever use consignment stores? Thanks! Jackie
I don’t donate to consignment stores and like to donate to the battered women’s shelter when I can.
Oh I can see the difference between the red and the berry sweaters on you. Shame about the red sweater not working. The style is so beautiful on you. I have a tulle mother-of-the-groom dress in royal blue that I love. I normally would not wear tulle but for some reason I love it. Maybe it is because I love the color so much.
Love, love, love the skirt. What size did you order? Reviews are all over the place on sizing
I’m wearing a small but could have easily worn a M
I think you look energetic and bold in red. Too bad you don’t feel comfortable in it, you look great in red.
I’m a busty petite apple (size 12 usually) and talk myself into buying things because they’re readily available, even though deep down I know they aren’t right for me. Examples: crewneck sweaters, dropped shoulders, patterns other than stripes, colors outside my palette that are “close enough,” and tops that are a size too big. I wore a chambray/denim shirt the other day that is too casual for my classic aesthetic, and I just didn’t feel good in it also because the color is wrong for my winter coloring. Yet I keep trying to wear it to make a column of color with my jeans. One would think that at age 68, I’d have this fashion thing figured out, but I’m still making occasional mistakes!
I struggle with the formality of clothes all the time because my life is so casual and my preferred esthetic is not.
That describes me perfectly!
I knew I was in great company Vyonne! Xo
Thank you for sharing something we all experience at one time or another. I have found a great line on QVC, it’s Susan Graver. She makes pants that have stretch, so if I put on an inch or two or lose an inch or two in my waistline, I’m still comfortable. I agree, that I have put together An outfit that I thought was perfect, only to look in the mirror and say O M G!😂
It’s better to catch in the mirror 🙂
I would really love the red sweater but I understand how you feel about clothes not feeling right. If it fits I think I should keep it but if you know you are not going to wear it then just donate it. I love the idea of tulle but don’t think it’s me. I agree the black with boots would look really nice. 🎄
I’m going to order a black one and try it.
No matter how many pairs of shoes and boots I have, I always seem to have failures in the footwear department. So frustrating!
That is very frustrating
Thank you for this post! The most educational for me was the faux leather pants. I knew it was wrong, but could not have sorted out what bothered me. I did not like the red sweater; I think it made you look top heavy. Maybe it has too much going on to be cropped, but you look Great with your shirts tied or tucked in.
I’m glad it was helpful. Taking selfies is so educational.
Loved this post!. It had as much value as others that present what works. I know how many times I try something on then add it remove until I’m satisfied. I’d love to see more of these.
Well, I hope I don’t have too many more in real life but I could recreate them for illustration purposes. Great idea!
I often find when I plan an outfit down to the last detail, it can look like I am in costume. Or like I am trying to look like the catalog model! It just feels too contrived. I guess that’s how to end up in a fashion rut! But what if you just think of it as your ‘signature style’! If it’s what you feel comfortable and confident in, and if it looks like you’ve made some effort, why not!
I agree!
I love that sweater and would gladly pay you full price🤣
I’m petite small and brunette
lol!
Great post! I can’t think of a specific outfit. But, I recently bought a pair of UGGS boots. My first pair. I bought them because everyone has them, so I should too. Well…..I hate them. I’ve done this before, bought something because I think I should like it or have it! Not my smartest move!
LOL, funny you should say this…I just bought some Uggs and am wondering if I made a mistake:)
Red is not my jam. I don’t wear it, even the orange-red that suits me. It’s hard to stay away from black completely, even though it’s not my color, so I try to keep it away from my face. Trust your color instincts.
Our instincts are really important and usually pretty smart.