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The average high for father's day is 23-24C which is just about perfect. Very long days too which I also like.
Easter is usually cool-mild, like 5-15C. On the high end of that average is nice, on the low end, not so much, especially since I'm usually looking forward to warm temperatures by then.
Halloween is basically the same, maybe a touch warmer, but the days are shorter and often more cloudy. Halloween still has leaves on the trees usually, and some late fall flowers, while Easter usually has spring bulbs and maybe Forsythias blooming. They both have their appeal, but I'll give Easter the slight edge.
Valentines day is basically the coldest part of winter. Winter can have mild 5C weather at any time, but in mid-February, there's still just as much likelihood of -20C Arctic air blasts as in January. On average, a high of 0C and low of -8C. February is usually more sunny than January but also more rainy (as counter-intuitive as that might seem) and less snowy than January. I like fresh snow but when it's just been sitting around for weeks and turning to ice, as it often is in mid-February, it's not so fun, so I prefer milder parts of winter like December.
Since I am in the Southern Hemisphere, my seasons are reversed compared to winter.
Valentine's Day [February 14], is usually warm and humid, with an average maximum of 26.5ºC [79.7ºF], and an average minimum of 19.5ºC [67.1ºF]. Rainfall has around a 30% of occurring, but comes in the form of a refreshing downpour. Dew Points are around 17ºC [62.6ºF] at this time of the year, which allows my skin to feel somewhat moisturised.
Easter [April 17 this year], is usually comfortable and semi-rainy, with an average maximum of 23.5ºC [74.3ºF] and an average minimum of 15ºC [59ºF]. Rainfall has around a 25% of occurring, but comes in heavy showers. Dew Points are lower, around 13ºC [55.4ºF]. This is about the time when my skin starts to get worse, as my skin is super sensitive to dryness.
Father's Day [For some reason, it is on the first Sunday [4th] of September], is cool and semi-dry, with an average maximum of 20.5ºC [68.9ºF], and an average minimum of 11ºC [51.8ºF]. Rainfall only has a 20% chance of occurring, as this part of the year is mostly dominated by foehn winds from the west. Dew Points are only 6.5ºC [43.7ºF], so my skin sucks.
Halloween [October 31], is comfortable and semi-dry, with an average maximum of 23.5ºC [74.3ºF] and an average minimum of 15.5ºC [59.9ºF]. Rainfall has a 25% chance of occurring, but it's usually light, and is the driest time of the year. Dew Points are still less than ideal, averaging 11ºC [51.8ºF], and my skin starts to slowly improve after this time.
Considering my chronic eczema, Valentine's Day is by far the best for my skin, as the warm and humid weather will allow my skin to breathe, wearing shorts. When the eczema doesn't flare up, Easter is the best precipitation and temperature-wise. Personally however, Halloween is the best, as it's approaching the summer holidays [mid-December to the end of January in Australia]. Currently, the cool and dry conditions of Father's Day isn't inviting, and I rank it last.
With Eczema: Valentine's Day >>>> Easter >> Halloween >>>> Father's Day
Without Eczema: Easter ~ Halloween > Father's Day >>> Valentine's Day
Personally: Halloween > Father's Day >>>>> Easter >> Valentine's Day.
Location: East of Seattle since 1992, 615' Elevation, Zone 8b - originally from SF Bay Area
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All of those would be a good chance of rain, probably close to 100%, but only Father's Day would be warm enough to avoid a heavy, waterproof jacket or coat. Halloween, Valentine's Day and even Easter there could be a chance of a freeze and/or snow.
Halloween is my favourite holiday and fall is my favourite season so its an easy pick for me. Around here I have seen Halloweens get as warm as the high 50s and as cold as low 20s.
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