Basic Black Field Boots – These classic riding boots go with everything. The Italian leather will keep you dry and form to your legs. I particularly like these because they have an extended calf option for those with wider calfs, mine included.
Bubble Umbrella – This umbrella is cheap and will go with everything, not to mention it’s super practical and classy (after all Blair Waldorf approves). It will keep the rain and wind out of your hair and the clear plastic makes it so you can see everything, even that cute dude checking out your even cuter umbrella. Sharing encouraged.