
This look includes three pieces in my closet that work exceptionally well:
- Madewell’s Perfect Vintage Jean (super soft and comfortable, no tummy pinching, gorgeous wash, not quite skinny jeans but still flattering and beautiful)
- Everlane’s Alpaca Crew Sweater (a staple in my closet since 2018)
- Vagabond kitten heel boots (that low heel and elegant toe!)
I’m so glad these items are in my closet.
However, I don’t really feel like myself in this outfit. I think it’s a perfectly great outfit. On the outside, it definitely works. But from the inside — that is, from my experience inside the outfit — it’s missing something that makes it feel like me.
That’s okay — good, actually — because it presents an opportunity to get curious. I can sit with this question for a little while: What is this outfit telling me?
I always learn the most about my style from the outfits that feel a little off.
Think of a recent outfit you’ve worn that didn’t quite work out — what might it be telling you?
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OUTFIT DETAILS
(If you see something you like, you can shop it and support my blog at the same time by using the affiliate links below)
Everlane Alpaca Crew Sweater (wearing L, heathered black)
Little Liffner Tall Tulip Tote
Madewell Mid Rise Perfect Vintage Jeans | Similar: Madewell Perfect Vintage Jeans
Vagabond Boots (old) | Similar: Anthropologie Kitten Heel Booties
James Avery Foxtail Chain Necklace (wearing 18in)
Jenny Bird Tome Medium Earrings
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Take good care of yourself today. Thanks for being here!






I too am wearing an outfit that doesn’t quite work despite liking all the pieces separately. I agree, it’s like a puzzle to figure out!
it’s the bag. swap it for a smaller, sleek crossbody! ❤️
I think Chantel is right. The overall size and large opening of the bag compete with the blouson sleeves and tunic length of the top.
It’s possible the kitten heel doesn’t quite work here either, though the pointed toe does. But definitely try it with another bag.
Thanks for sharing something you’re wanting to tweak. Helps me to think what does/doesn’t work despite the individual pieces being fine.
Maybe you do need to include something that is not chic and sleek and minimal to break it up a little, e.g. messy hair / a different hair style, a sporty bag (or a slouchy bag).
Otherwise it’s to expected, generic pinterest chic.
love it thoug!
Maybe its the proportions? Pant leg/ boots and big bag/ big shirt. Thanks for sharing this inquisitive moment.
I completely understand what you mean. It is so interesting how that can happen – the outfit looks perfect, but feels off. I agree with the above comments here – try swapping out the bag. How about a canvas tote? To make it feel more casual. I think the outfit looks a bit too structured/styled for what I am seeing as your style these days. Combination bag and shoes may be too much, even if I personally like the combination. Would love to see your updated version if you figure it out!
The boots seem to be the issue here, making the outfit feel dated. The look reminds me of how jeans and boots were paired in the mid-90s. Interesting to think about why this look doesn’t work for right now!
I think it’s the proportions as well. To me the jeans look too skinny with the sleek narrow boots, baggier jeans with the kitten heels would give it a more updated look. Also your style is really sporty so I think maybe you’re missing that sporty/casual element. I agree about wanting to see an updated version of the look!