What to Wear on Rainy Date

In rainy weather, it’s easy to feel like you’re stuck indoors. But if you want to go out and have a good time, that doesn’t have to be the case! I know how hard it can be to get dressed for a date when the weather is bad. You want your outfit to reflect your personality and mood, but you also don’t want to ruin someone else’s shoes by slipping on the sidewalk. That’s why I’ve put together this list of rainy-day date outfits that are cute and functional without being too boring or too casual.

What to Wear on Rainy Date

The rain is coming down, and your date is waiting for you. What should you wear?

It’s a question that has plagued many a fashion-forward person in their time, and we’re here to help you answer it.

Rainy days in the fall and I well…we don’t get along. Particularly on a special night, when I’m trying to look my absolute best. A fall first date outfit is clutch, since fall rain was practically made to destroy any sense of style (for me, at least). Where spring and summer are so ideal for first dates (hello, having a drink or meal in the beautiful weather outside and being able to ditch a heavy coat), the fall rain and wind isn’t exactly ideal.

Few things are more exciting than a first date. You’re getting ready, probably feeling yourself, checking your cute self out in the mirror. You’ve planned out an outfit for days, have picked out the perfect first date spot, and have effectively done your Instagram and Facebook stalking. But when you open that weather app and see those three little blue lines coming from an angry cloud, you basically have to rethink your whole look.

Enter the rainy day essentials that are here to save the day. Your first date doesn’t have to be ruined just because of the rain! Living in New York City, I’ve learned to keep some wardrobe essentials around for when the weather changes. And my rainy day starter pack is pretty fool proof, if I may say so myself.

So, if you find yourself on first date night with anything from a drizzle to a downpour, these essentials should be able to help you out.

  1. A Stylish, Yet Functional Raincoat
  1. A Practical Trench Coat

With a pair of your favorite denim, this is a killer look.

  1. A Heeled Rain Boot

To a put a little pep in their step.

  1. A Little Extra Shine

A little pointed toe is just the touch you need.

  1. A Good Umbrella

This polka dot is so cute!

  1. A Pop Of Color

When it’s dreary outside, it’s nice to have a little bright accessory.

  1. A Cute Baseball Cap

With a sassy little message.

  1. A Classic Cap

A classic hat beats out anything.

  1. A Handbag Slicker

How amazing is this handbag raincoat?! This way, you can wear your cutest bags out.

  1. Or Better Yet, A Clear Handbag

Better yet, a plastic bag altogether!

  1. An Anorak Coat

I’m obsessed with this color.
If you’re the kind of person where a storm just ruins your whole day, don’t worry: It’ll all be okay. You can still wear some super cute outfits—complete with rain boots, an umbrella, and jacket—that might make you actually look forward to wet weather. But if you’re like me and love those gray, rainy days (I mean, I’m from Florida where it downpours at, like, 3 p.m. every day during summer), then I’m sure you don’t need any convincing that you can still make the most of your outfit.

There are so many routes you can go with your outfits, whether you want to keep things sophisticated in a classic black raincoat or go for a more eclectic or sporty look. Obviously, your clothing choices also depend on how hard it’s actually coming down or if the forecast will clear up later, but if you’re stuck thinking of cute rainy day outfits, we rounded up 18 here for you so you can stay dry—and look super stylish at the same time. (Also, since we’re on the subject, click here for some lightweight summer jackets and rainy day activities to do while you’re at it.)

What To Wear On Rainy Days

Lately, the skies have been dark and the days gray but that is nothing to worry about if you are trying to look cute and stylish.

Instead of letting a rainy day get you down, you can dress it up cheerfully. From soaked clothes to squishy shoes, your perfect ensemble could be in havoc just because of a light shower from above.

Here are some quick tips to keep in mind when dressing for rainy weather or dealing with unpredictable weather in general.

Invest In Rain Boots
No matter the outfit you are wearing, throwing on knee-high boots is not only stylish but will keep you dry. It especially goes well with skinny jeans.

Consider A Scarf
Protect your hair with a scarf during the rainy days. A thin scarf to tie around your hair can keep flyaways at bay and protect against frizz.

Style influencer Saufeeya Goodson in boots and beanie _ Photo- Savoir Flair

Layer Your Outfit
The weather can be tricky and unpredictable so to avoid being caught unawares, it is advised that you layer your outfit in case of a sudden change of weather. If rain is on the radar then layer your outfit so that you can ditch outer layers if it suddenly gets warm and dry or to keep yourself warm in case the weather takes a turn for the worst.


A Pop Of Colours
Just because the skies are grey does not mean that you have to wear dull colours. Brighten up your day by adding a pop of colour to your outfits. It won’t be a bad idea to add a pop of colour like red, yellow or blue. If you don’t like bold colours, you can lighten things up with muted colours.

Best Rainy Day Outfits and Tips to Ensure Rain Never Ruins Your Travels

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Rain can be a nuisance when you travel if you’re not prepared. Don’t let rain ruin your trip. Here are some packing tips and outfit ideas to help you make the most of the weather – rain or shine!

I like to be prepared for all types of weather, but sometimes when you choose to travel somewhere during the country’s rainy season, you need to be even more prepared for the weather when planning your travel capsule wardrobe.

Rain can be a nuisance if you haven’t prepared for it. However, if you have the essential items, it will just be part of the trip, not a deal-breaker.

Here are a few tips on how to ensure rain will never ruin your trip:

Rain Jackets for Women
Waterproof Trench Coats for Women
Best Travel Umbrella Recommended by Readers
Cute Rain Boots for Women
Sturdy Duck Boots for Women
Womens Waterproof Leather Boots

The type of clothing you’ll need will depend on the day’s activities and how heavy the rain will be. Here are some top tips and outfit ideas some drizzle or a downpour will just be any other travel adventure!


Repel Windproof Double Vented Travel Umbrella

Should I pack an umbrella?

When we think of a rainy day outfit, we often envision an umbrella. However, if rain is not on the horizon, don’t bring one. However, if you’re traveling to a temperate climate in the spring, the probability of it raining is higher, so bringing a compact travel umbrella is suggested but not necessary as you can always buy one in your destination if needed. If you’re looking for suggestions, read this best travel umbrellas post!

Always, always check the weather forecast before your trip. Once you’ve researched the weather, you can focus on creating a capsule travel wardrobe, which should easily fit in a carryon suitcase with the help of packing cubes to compress your clothing.

Tip: I’ve never packed an umbrella when traveling to Europe because I know they’ll be cheaply sold at any tourist location by people on the street looking to make a buck.

UGG Chevonne Ankle Rain Boot

What type of shoes should I bring?

Whether or not to pack rain boots is always one of the biggest dilemmas when planning your rainy day outfit while traveling.

Generally speaking, don’t pack rain boots unless you can get multiple uses out of them. However, if you feel you need them, stick to ankle rubber rain boots as they’re easier to manage. Take a look at the best rain boots for 10 options that might work for you!

Sperry Saltwater Waterproof Duck Boot

There may be an odd trip where you might be outdoors a lot. For example, if you are staying at a farm, planning to visit the countryside, or hiking in a forest, women’s duck boots can protect against mud or manure. Check out this post for a full list of waterproof duck boots!

Blondo Women’s Villa Waterproof Ankle Bootie

However, if you’re traveling to a city and just want to be prepared for the possibility of rain, waterproof leather boots such as the ones shown above are a great all-weather shoe. They’ll go with all your outfits and can be worn in various settings. The Blondo Villa Waterproof Boot is so popular among readers and the TFG Editor-in-Chief, we did a video review on them and a post.

Watch this video review on the Blondo Villa Waterproof boot!

Packing a functional yet versatile style can help you avoid the need to pack an additional pair of boots just for rain (aka rain boots).

Check out more of the best waterproof boots for travel.


Eddie Bauer Girl On The Go Waterproof Trench | Sizes XS-3X

What type of coat should I bring?

Planning what to wear on rainy days doesn’t mean you need a utilitarian look. You just need to plan the right clothing based on your itinerary. There are a few outerwear options you could wear in the rain: a raincoat, a regular coat with a hood, or a poncho.


Columbia Arcadia II Jacket | Sizes XS-3XL Plus

If you’ll be doing a pastime such as hiking or have several outdoor activities planned, we suggest a lightweight foldable rain jacket that you can put over other layers.


Cole Haan Trench Coat With Hood | Sizes XS-XL

If you’re visiting a city and spending more time sightseeing indoors, aboard a coach, or using taxis to get to and from destinations, opt for a waterproof classic trench coat with a hood or another spring jacket—review this article for more timeless trenches!


SaphiRose Hooded Zip Up Poncho

If you aren’t expecting much rain, but want to be prepared, a cheap, packable poncho that you can throw into your bag is an option as well. It’s an often-forgotten must to add to your list for rainy day outfits.

Read this post for stylish travel raincoats for women!


Zella Live in Leggings | Sizes XS-XXL and Plus 1X-3X

What clothing should I wear?

When deciding what to wear on a rainy day, leggings, or dresses worn over tights are always a good option. Leggings, and especially tights, dry quickly because they tend to have porous material.


Karen Kane A-Line Jersey Dress | Size XS-XL

Make sure to avoid cotton leggings or trousers and stick to synthetic fabrics for dresses. Jeans aren’t the best option for rain either; their thick fabric holds moisture against your skin and takes longer to dry.

Take a look at the top leggings for travel!


Too Faced Better Than Sex Waterproof Mascara

What make-up should I wear?

Even with an umbrella and the right jacket, you can’t avoid the wind blowing some water into your face. So, deciding what to wear on a rainy day also includes makeup!

Obviously, waterproof mascara is a given if you do plan to wear makeup. Tinted moisturizer is also great option because it tends to soak into your skin more than foundation which rests on the surface. This will also help avoid brown streaks dripping your face. Additionally, an all-over color stick will work better than just powdered blushes or eyeshadows.

Our readers shared their favorites for the best waterproof mascara!


NARS The Multiple

Color sticks make great travel products in general! Along with working well in the rain, they are multi-functional and pass through security easily. Make sure to bring them along with you on your next adventure, rain or shine.

Search for more waterproof travel beauty products such as eyeliner, eyebrow pencil, mascara, and more that can help you look and feel good in the rain!


Cole Haan Double Breasted Packable Rain Jacket | Sizes XS-3X
(Model Demonstrating Packing Method)

Will the rain ruin my trip?

Of course not! Getting caught in the rain doesn’t have to put a damper on your trip. In fact, make the most of it. Purchase a brightly-colored umbrella that will stand out even in the drabbest weather or bring a lightweight raincoat is a more practical solution.

You can roll it up when you don’t need it, as demonstrated above, or store it in the bag you’re carrying. Some of those moments have been my most treasured travel photographs. Enjoy a hot bath at night, if the rain made you chilly.

Experiencing a traditional rainstorm in places such as England is all part of the cultural experience. Just make sure you carefully plan what to wear on a rainy day and bring the right gear.

Tip: Try to plan your itinerary according to the rain. For example, save museum visits and other indoor activities for rainy days and make the most of the sunshine when you can.

What to Wear on Rainy Days Outfit Ideas

Below are some examples of specific capsule wardrobe ideas for mild to heavy rain:


T-Shirt | Socks | Bag | Bra | Pants | Rain Jacket | Boots

Rainy Day Outfits: Hiking or Exploring

A quality rain jacket, good hiking boots and a waterproof bag will be good to have with you. A bra made with synthetic material is also good to help you dry faster. (Rain and sweat! Double bonus.)

If you’re going to be outside hiking or exploring, you’ll definitely want to wear moisture-wicking pants and socks. Having a good pair of socks that keep your feet dry, and not swampy is key. Your feet will already sweat while you hike, additional moisture can increase the likeliness of developing blisters. Make sure to purchase socks with a wool blend.

Trekking in torrential rain or snow? Pack waterproof pants and a plastic poncho as well. v

Rainy Day Outfits: Light Rain

If you’re walking to and from destinations in light rain, a good trench coat will help to keep your outfit and hair dry.

Tights and a dress are a good option, especially if you don’t want to wear hiking pants around a city. Tights are also made of synthetic material that dry fast.

For an outfit that will take you from rain to ritzy, wear leather boots that are waterproof and style-forward. Leather boots will keep your feet dry, and will be able to withstand mud as you encounter it. You can use a water resistant spray to help keep water out and protect your shoes.

Pair with black tights and a dress that can work for both day and night. Finish it off with a waterproof trench coat and a compact umbrella that can easily fit in your purse.

You can easily roll up your rain coat into a packing cube without any issues until you need it.


Jeans are OK for light rain although we don’t recommend wearing them for heavy rainy days or when you’re outside in the rain for extended periods of time. Opt for leggings instead. (Wearing wet clothes in cold temperatures can cause hypothermia.) Learn about how to choose the best fabrics for travel.

A compact travel umbrella will block a drizzle, and can be stowed in your day bag when not in use. Don’t be afraid to pick up a brightly-colored umbrella. Especially if the day is cloudy, it can really brighten up your photographs.

However, if you opt to skip the umbrella a light hooded jacket will usually work just fine. Wool blend socks are key to keeping your feet dry.

Rainy Day Outfits: Outdoor Sightseeing in All-day Rain

Choose one of these travel rain coats for women that fall below your hips. Alternatively, I recommend a durable poncho that keeps your whole body dry, but also gives you some breathability and flexibility.

Believe it or not, a dress and wool-blend tights, and a small leather bag (which is also waterproof) is any easy to wear outfit in the rain. Your clothing can dry easier, too.

Choose clothing you wear comfortably under your poncho or rain jacket. For heavy rain, we recommend a sturdy umbrella (a compact option from home or wait to purchase one abroad if needed).

While you don’t have to pack rain boots for most trips abroad, a pair of waterproof boots like one of these is definitely encouraged. You’ll see that there are many stylish options to choose from!

Now, would be a good time to use your water-proof camera, like a GoPro, to take photographs. Brightly colored lipstick and dangle earrings make a fun way to make you feel flirty, even in the pouring rain and cloudy weather!

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