Personally, I don’t mind rainy days…as long as I have to go anywhere. Rainy days when you have places to go, however, can be a special kind of suck, especially if you aren’t prepared with the right rainwear. There isn’t much worse than soggy feet or the feeling of being cold and damp.

How to Look Stylish on Rainy Days

With the rainy spring season around the corner for many, I have put three rainy day looks together to ensure that your feet will stay dry and you’ll be free from that dreaded dampness.

Outfit #1


I own a pair of rain boots. Being a New Yorker, they can be sort of important because we walk a lot. However, for many people, their time spent outdoors is much more limited. This does not mean feet don’t get soggy, especially when walking through a downpour. Rain can also ruin nice shoes. No bueno.

Many people don’t realize that all of Aquatalia’s shoes are weatherproof, even their sandals, making them an ideal brand to look at if you need work shoes and loathe the idea of dragging a pair of rain boots back and forth.

I styled these block heel Aquatalia pumps with a cute sweater dress from L.K. Bennett. Over it, I layered a stylish red trench from Something Navy. While it is cute, it is cotton so don’t expect it to be the perfect trench for a super rainy day. I finished the outfit with a navy bucket style rain hat, nylon Longchamp bag and navy earrings.

Outfit #2


Before getting my olive Tinsley chelsea style rain boots from Sam Edelman, I wore Hunter boots. They really are superb boots and live up to their reputation. I styled this burgundy pair stylishly with grey jeans from AG, a grey v-neck sweater from Equipment and a Canada Goose rain jacket in a blue meltwater shade. I finished the look with a lightweight plaid scarf from Treasure & Bond and casual navy bag from Baggallini.

Outfit #3


In this last look I styled a casual outfit for rainy days that doesn’t require rain boots. I used these casual weatherproof slip-ons from Blondo that I styled with a pair of boyfriend jeans from Kut from the Kloth and added this relaxed breton from Eileen Fisher and water repellant hooded utility jacket in a denim pattern. I finished the look with a floral LeSportsac bag that adds a punch to the look without a lot of fuss.

The key to rainy day style is to be prepared. Depending on where you live, you may need pieces like this a little or a lot, but having these things ahead of time will ensure you will be able to pull together for even the most inclement of days.