Frustrating, though, to save pieces for a big reveal and then to have it fall flat (in your eyes). I've been there.

NOT a bad outfit, Lisa, looks color coordinated and intentional, just not up to your/our highs!:-)
Now, this is a perfect example of the soul sucking effect of that beige in that sweatshirt---I learned to be cautious of big amounts of that pale beige on my body as am blonde, too. Instead I love dark patterns with only small amounts of this color for my top half, or if having a metallic shine and texture (say Runcarla's golden beige puffer-which I have a similar one) and I swear the tie-dye sweatshirt would look gorgeous on you if made of a bigger contrast color scheme like bl&w! Plus, the sweatshirt and the vest in the same colorway is just too much for you/us. Try the same outfit with a charcoal puffer vest and would work much more better. Or the tan vest with a charcoal long sleeve top -also great. To be frank, I have no problems with the jeans elasticated hems included. I love them with the cognac loafers (which don't feel that masculine to me here-but I avoid laces on my shoes for that same reason) just pair it with a crisp shirt/blouse on top!

Ok, I am sorry you felt blah in this outfit, but I love the sweatshirt on you -- you look really pretty in these tones! I also love the vest with the shoes (and like each item on its own). I think maybe it was too warm to wear this on the day you chose it (or later in the afternoon of that day) and that will make anyone feel gross.

Also, you are super hard on yourself! As Angie pointed out, you might feel a bit better with slightly more "hard" edge to your look -- it's your comfort zone, so to speak, and this may feel overall a bit soft. OTOH, you may be trying to evolve your style just slightly in that direction and it may take some time to find the balance that works.

Especially because you have to wear black at work, you end up in conflict about it. In your previous (before Refit) life, black was your basic and a foolproof. Now, you still like it, but get bored (understandably!) with wearing it all the time, plus you share some concerns about its flattery or lack thereof (although I think you still wear it well). In any case, it's a bit of a transition period in more ways than one -- weather, the place of hard edge or black, and, um Covid. UGH>

Again, all such terrific comments, ideas and insights. The beauty and value of the forum playing out right here.

I'm struggling a bit (I mean, it's all relative to other far more important issues in the world) with finding "my" wardrobe now that I don't have a fashion/retail/style focused job. I consider myself semi-retired even though I work almost full time - and now that I don't have the same kind of social life I used to, my justification/need for "nicer" clothes isn't the same. It's a balance I've yet to find - and this outfit is a perfect illustration of the attempt

I’m late to this and others have already suggested what I would have, so nothing more to say besides I think all the pieces work for you, perhaps just not all together! I find this true for me too. Sometimes I just need to crack the code that gives my outfit the right balance of ease and structure, color and contrast, edge and flattery, etc.

Lisa - I think Angie hit is that you might be happier with more contrast. The value of the sweatshirt is close to your skin tone. Adding a scarf (like you McQ) close to your face or a different higher contrast topper would help put the focus on you. I like the vest/sneaker combo but maybe with a dark floral blouse that picked up your colors. The pieces are nice, but I would pull them apart and try styling them individually. Push the contrast and see if that makes your happier. But honestly, you look great. Not my favorite outfit the blazer outfits I swoon over but very nice look probably just too warm for this time of year and agree you overheat you will hate what you have on. We all would!!

I am a person who definitely chooses pieces based on color more than anything. And cognac is definitely a good color for you. But that may have been the issue with this capsule -- that it was more based on color matching than anything else. As others have suggested, remixing with pieces that are more in line with your tailored, feminine preferences could work better.

(I have a really hard time wearing sweatshirts in a non-gear way, btw)

Cognac capsule: what a great idea! The last few months I have been leaning toward brown tones. After experimenting with dark brown I'm now trying medium shades such as camel and cognac.

I think you look great. I can see how a higher contrast is better for you, but I like your outfit today just fine. Many times I dress too warmly because it's cool in the mornings and then later I'm sweating and feeling foolish.

Now those shoes: I love them! I've been looking and looking this last week for a pair of camel or tan or brown shades of walking shoes. Unfortunately, orthopedic is my style these days, but your pair look quite sleek to me. I haven't been able to find anything in my size that I like--the shoe manufacturers don't seem to be keeping up with color trends. I'm not familiar with your brand, but I'm going to check on it.

I always look forward to your wiw postings Lisa. All great pieces as others have already mentioned, a higher contrast top would probably make you happier.
Love your comment about the sneakers looking ‘orthopaedic’ - totally get that as I face the challenge of finding comfortable shoes that look good too.