biglmbass

Yes. Good to have a back-up pair. Also good to have a 1/2 size larger pair for winter use to better accomodate thick socks.

lasauge 

As others have said, if you have multiple pedal systems or different clipless shoes for different purposes (road, MTB, commuting, cold weather, etc.) then those are obvious reasons to have multiple cycling shoes. But for pure road riding if you have only one pedal type then I think it's fine to have just one pair - just pick shoes in a neutral color (black, gray) and avoid shoes that are winter/summer specific and you're set. Road shoes dry quickly enough that unless you're remarkably sweaty, or riding in downpours without covers is something you're likely to need to deal with, having just one pair is fine. Personally I have two pairs of road shoes these days but found that I reach for my Sidi's 100% of the time when setting out for a ride from home, so the second pair now lives at the office for use on lunchtime rides.

black_box 

If you're trying to get by with summer shoes, replacing the insole with a cold weather/ foil reflective insole really helps. I also put black gaffer tape (not duct tape, it leaves residue) over the mesh in the toe box to close off some of the air.

jaxgtr

I have 2 pair that I use. One is an older pair that I use for the trainer primarily and if I plan to do any off road and there is the possibility of nasty and wet. I also use these if the weather on the road looks heavily like rain. I have another pair that I generally wear on the road only, in good weather. I got caught in the rain in these once and they did not drain as well as I would have liked.

jaxgtr

Miles2go

100% of my riding is in one pair of black Sidis. I have a slightly older pair of silver Sidis as a backup, in case a shoe breaks, etc. I've never needed a spare pair of shoes in the decades of riding that I've done, but the spare pair take little room in my cycling closet.

Miles, smiles & tailwinds!

dilbert2000

My wife has three pair - vanity.
I had a pair from about 10 years ago. The buckle broke. Could not find a replacement anywhere. This was early in the pandemic. Could not find new shoes anywhere. Got lucky and found a pair of S Works that fit. Cost me $400. I'm an average size, which may have made it harder. It was their last pair. I bought them.
If I had the money, I'd get a second pair to make sure I always had one available. Kinda like tires and tubes. There are always spares in the basement.

woodcraft

About the same as the need for more than one bike...

Shimagnolo

One pair for summer;
One pair for winter.

Voodoo76

If a shoe fits really well it's worth having another pair or two so you don't have to start all over again when they stop making them. Same goes for saddles.

ThermionicScott 

I used to try to make one pair work for everything. But I've come to prefer tighter retention on the fixed-gear, and SPD sandals with much looser fit and retention for the other bikes.

kstephens

I have several pairs for different reasons - I have a couple pair of SIDI for dedicated road or long rides (spd and spd sl - but are by far the most comfortable for longer days on the bike, some old lace up cannondales with heavy tread - those are my commuter/errand/grocery getting shoes - they are spd, but the sole is a tad more flexible and walkable, and a pair of Shimano sandles that I wear for quick summer rides with wife and kids.

rsbob 

One pair with minimal vents for cold weather and rain rides and another well vented pair for the summer heat since my feet swell when hot.

PeteHski

The simple answer is not really.

But if you ride often indoors on a trainer, then it's a good idea to have a pair dedicated to that as they get seriously sweaty.
Likewise you could have a pair that you use for bad weather and a "best" pair for dry summer use.

I happen to have 3 pairs of road shoes, 2 pairs are identical (but different colours) and 1 pair are a higher spec. I use 1 pair on the trainer, 1 pair for wet outdoor rides and my best pair for dry outdoor rides.