Our early winter always tends to be rainy and while most of us are dreaming of a white Christmas, us Southerners will be gearing up for a soggy one instead. It's a little bit less magical, but that's why we always watch White Christmas.

Most of the time rainy days, with the fireplace crackling and the hot cocoa simmering, are delightful, but the moment you step out into the soggy outdoors hair becomes bedraggled, socks turn soppy, and fingers freeze just a bit.

So, to combat the inevitable chilly winter rain, I've put together a rainy day capsule wardrobe for both men and women. If you're missing a piece or two from the list, add it to your Christmas list!

Sperry Rain Shoot 2
Sperry Rain Shoot 4

8 Rainy Day Capsule Wardrobe Essentials

Let's start at the top and work our way down. I believe the same general pieces and principles of a rainy day capsule collection work for both men and women.

  • Hat - my personal preference is a baseball cap but a beanie is a bit more useful when it's chilly.
  • Base layer – think thermal, waffle knit, henley or even t-shirt. Just something fairly form fitting to keep your body heat in.
  • Sweater or Hoodie – a hoodie is supremely practical if you don't have a hood on your jacket or a hat handy. But a sweater might be less bulky under a rain jacket.
  • Rain Jacket – this must be a true water-repellant jacket. None of this trench coat nonsense. We'll take brands in a moment, but the bottom line is it must be able to successfully keep the water off.
  • Black jeans – I naturally always reach for my black Sezane jeans on rainy days. There's something about dark denim that is comforting in the rain.
  • Cozy cabin socks – there is nothing more luxurious than cozy, thick socks on a rainy day.
  • Waterproof boots – much like your jacket, these boots are supremely important to a successful rainy day capsule and must actually keep the rain and puddle water out.
  • Umbrella – truth be told I can't remember the last I carried an umbrella, but truly it is an important item in a rainy day capsule.
Sperry Rain Shoot 1

Reviewing the Sperry Rain Boot Collection for Men and Women

Dry feet = happy body during a chilly, rainy day. I've found that even if my jacket isn't 100% waterproof and I forget a hat or gloves, if my feet stay dry I'm so much more comfortable and much less likely to catch a cold.

Sperry has long been known for their Duck Boot for both men and women - a rubber bottomed, leather upper boot that's very classy and very preppy. And after having worn mine for years it was time for a little upgrade (or update, rather) to their chelsea boot style rain boot the Torrent Chelsea Boot.

Lee has worn chelsea boot style rain boots for years now as well and since his were officially cracked on the bottom we turned in his older pair for the men's Cold Bay Rubber Boots.

Women's Torrent Chelsea Rain Boot

Shop the Boot

Quick Facts:

Sizing: women's size 6 // runs a little big, maybe like a 1/2 size but with cozy wool socks they're a good size

Colorway: I have the light green color but they also come in a full black and then black with a pop of either purple, orange or yellow neon soles.

Materials: 100% rubber outer shell with a micro-fleece lining that makes them cozy but not hot. Fully waterproof not just water resistant.

Price: $79.95

Apart from the boots being a little large without thick socks, these were love at first step. They're comfortable for walking in with a thicker sole but they're not quite as clunky as other rain boots I've worn in the past.

I will say you do want to wear socks with these. I did slip them on to check the mail without socks and they rubbed painfully on my heels the whole time.

I also have worn them out in the rain and can confirm my feet stayed very dry! The slip-on feature of the boots is genius too. They're almost too easy to pull on or kick off.

Sperry Rain Shoot 21
Sperry Rain Shoot 6
Sperry Rain Shoot 18
Sperry Rain Shoot 7

Men's Cold Bay Rubber Chelsea Boot

Shop the Boots

Quick Facts

Sizing: Lee wears a standard size 12 in every boot and these were maybe a full size too small. Definitely order up a size if you want to wear them with thicker socks.

Colorway: these boots are the Dark Brown but they have 5 colors in total include a classic black, all green, and a fun colorful option.

Materials: waterproof rubber shell with a micro fleece interior

Price: $94.95

The biggest drawback to these were the sizing. I'm not sure if they were mis-marked in production but they were difficult for Lee to make comfortable - due to the sizing only.

The interior is just as cozy as the women's version with a thin fleece for extra padding and the fully rubber exterior is fully waterproof which is great for anything from getting to work in the rain or doing yard work in the spring.

Sperry Rain Shoot 12
Sperry Rain Shoot 9
Sperry Rain Shoot 8
Sperry Rain Shoot 14

And to give you an idea of how to style these boots when you're starting out the day to grey and gloomy weather, here are some specific outfits to keep you warm and dry.