2017 Update: We still stand by this advice on when is it time to stop wearing tights to work — links have also been updated below. You may also want to check out our most recent roundup of Sleek Strappy Pumps for the Office if you are searching for the perfect shoes to wear with tights.

When is it time to stop wearing tights to work? What about ankle boots or knee-high boots? Is it determined by date (e.g., Memorial Day), weather, both, or something else? What do you do in the interim? Reader A wonders:

Will I begin to look ridiculous/weather inappropriate for wearing ankle boots to work? Same questions for tights/stockings with dresses and skirts?

I noted a similar conundrum on last weekend’s Open Thread: it’s almost May! It’s 60-70 degrees outside! So: it feels too warm for boots and tights — but it’s too cold for bare legs and peep toes. We’ve talked about summer tweed just recently, as well as bare legs in winter, but that was a while ago.

(Pictured: DKNY has these Light Opaque Control Top Tights in a number of different shades — I’ve pictured the chocolate, but I also like the flannel gray and the light beige “caramel.”) 

Tights: For my $.02 regarding tights, I would say that the key for me is whether the tights are dark and/or opaque — and I would probably put a red light around May 15, with a yellow light starting a few weeks after spring officially begins (this year it started March 20).  There are so many options beyond dark tights, such as pantyhose, semi-sheer tights, and tights with a wide knit, and skin-colored tights — as well as, you know, pants.  I would avoid character/cutesy/costumey tights for work (such as this, this, or this), but otherwise there are a ton of options.  The yellow light would turn to red (for me at least) if it were a warm day, a sunny day, or a humid day — as well as if it was a “big” day at the office.

Ankle boots: Ankle boots are an interesting question because right now ankle boots and skirts (and ankle boots and ankle pants) are so much more popular than they were a few years ago.  Assuming ankle boots are ok to wear with dresses for your office (a big assumption!), I suspect the ideal answer is to transition to “spring boots” in nude-for-you tones (here, here, here), perforations ( here, or for example), and more, but know your office!  I do think any boot would strike a traditionalist as odd in the middle of summer, even if it seems like everyone (at least everyone in the Forever 21 set) is wearing boots all summer long with shorts and sundresses. So — for “spring boots” only — I would put the yellow light on boots at May 15, and a red light on the first official day of summer (this year it’s June 21).  For winter boots I would probably put the red light on May 15, and a yellow light a few weeks after spring began, much like opaque tights.

Knee High Boots: Finally, Reader A didn’t ask about knee-high boots, but I threw them in because I’m curious to hear what readers say — I’ve been keeping mine out to wear in the evenings with bare legs and dresses, and I still see a ton of people wearing them on the street with skinny jeans and leggings.  I’d say knee high boots are closer to opaque tights for me in terms of red/yellow lights — even for nude-for-you boots, I’d put the yellow light around the first few weeks of spring (this year the season began March 20), and the red light at May 15.

Ladies, I’m really curious when do you stop wearing tights to work?  How about ankle boots and knee high boots? Do you agree or disagree with my rough red/yellow light estimates? 

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Picture below via Stencil.