Nemosmom, I bet those brown boots are sublime with your hair!

Like Jenna, I think "dated" is becoming a dated concept (I've mentioned that in many a blog post) - and especially with shoes and accessories. Clothing is a little more complex. YES - there are trends. But DYOT rules supreme, and trends are less and less relevant.

#1 - Fryes make an apocalyptic statement. Iconic.

#2 - Stick those under a midi or maxi skirt and you're in business! Very clean tailored fit - if the heels are manageable - which you mentioned you don't mind.

#3 - these I like the least because of the way they fit up top. Too tall and wide. Again, stick them under a midi and you hide the ill-fitting part

I know you don't wear skirts and dresses THAT part you will need to ponder.....

Thank you everyone for your responses! I definitely find myself more and more in the DYOT camp these days. You all have given me great suggestions. SaraD8 - yes, I should look at my non-holding zone boots- they are all ankle-height, but might be worth a look. I think a re-eval in Fall is in order. These tall boots seemed like a good place to start - they are large and take up valuable space in my drawers!

Nemosmom you have inspired me maybe I’ll take a baby step and at least look through my summer dresses... I’m sure there’s some I could cull out of the lot...

I agree with the majority here...I like all but I do think #2 feel a bit dated to me... but as Angie says, maybe my concept of dated is dated!

I think the same as Angie.

I think the Frye boots are pretty classic, and are worth keeping. The suede ones are such a rich autumn feeling boot that they are different enough from the winter feel of the Guess boots. I'm hopeful that the whole WFH coronapocalypse thing is temporary and that we all get to actually go out and about eventually, so I'm not getting rid of anything that doesn't work for my lockdown style unless it's something that I know doesn't fit or that I truly won't wear even after lockdown.

That's a great approach, Cindy! I need to be careful not to toss everything in favor of pjs

I would 100% keep the first and third pair. The second pair, I wasn't sure about only because I had a similar pair and the slight upturned toe started bothering me style-wise at a point - BUT reading your comments as well as Angie's I'd say, keep if you have room for them ... because the style may feel fresh again with the next change in trends, and I agree that DYOT is the best way to go!