21 Chic Rainy Day Leggings Outfits for Women Who Want Comfort and Fit

Rainy days always make me reach for leggings because I want to feel cozy without giving up on looking cute.

I have spent way too many mornings trying to make leggings feel polished enough for errands, coffee runs, and those gray weather days that drag on.

If you are into outfits that stretch with you and still feel put together, this list is exactly the kind of inspiration I love saving.

My goal here was to show how simple leggings can still feel chic, flattering, and totally wearable even when the weather refuses to cooperate.

Classic Trench and Black Leggings Combo

This outfit pairs sleek black leggings with a beige trench coat that falls just below the knee.
A simple neutral sweater underneath keeps the look clean and polished, while white sneakers add a fresh casual touch.
The overall vibe feels timeless and city ready, perfect for walking through wet streets without feeling overdressed.

I love how this look feels effortless but still very put together.
The trench instantly elevates basic leggings, and the neutral palette makes everything look intentional.
It is one of those outfits that always makes me feel confident, even on gloomy rainy days.

Cozy Knit Sweater With Sleek Leggings

Here we see soft gray leggings styled with an oversized cream knit sweater that looks warm and inviting.
Ankle boots ground the outfit and add structure, making it ideal for chilly rainy weather.
The relaxed silhouette feels cozy while still looking stylish enough for everyday errands.

This is the kind of outfit I reach for when comfort is non negotiable.
The oversized sweater balances the fitted leggings beautifully and creates a flattering shape.
It feels easy, soft, and perfect for slow rainy walks.

Long Wool Coat With Coffee Run Leggings Look

This outfit features black leggings layered with a long charcoal coat and simple dark boots.
A neutral top underneath keeps the look understated while the long coat adds drama and warmth.
The vibe is minimal, modern, and perfect for a rainy morning coffee run.

I love how chic this feels without trying too hard.
The long coat instantly makes leggings look elevated and intentional.
It is one of those outfits that makes rainy days feel a little more stylish.

Utility Jacket and Earth Tone Leggings

Olive green leggings are paired with a cropped utility jacket for a sporty yet urban look.
White sneakers keep things practical and fresh, while the fitted jacket adds structure.
The color palette feels grounded and perfect for overcast weather.

This outfit feels so wearable and flattering at the same time.
The jacket defines the waist and balances the leggings nicely.
It is great for days when I want comfort but still want to look put together.

Sporty Hoodie With Relaxed Rainy Day Layers

This look combines dark leggings with a light gray hoodie and an oversized rain friendly jacket.
Chunky sneakers add a sporty edge and keep the outfit practical for wet sidewalks.
The overall feel is casual, cozy, and made for movement.

I love outfits like this for rainy days when comfort comes first.
The layers make it functional while still looking cute and intentional.
It feels relaxed without looking sloppy, which is always a win.

Casual Puffer Vest With Everyday Leggings

Black leggings are styled with a gray hoodie and a lightweight puffer vest for extra warmth.
Sneakers keep the outfit grounded and ready for walking around town.
The layered look feels practical, modern, and perfect for unpredictable rain.

This outfit feels like a reliable go to for busy days.
The vest adds shape and keeps the look from feeling too basic.
It is comfortable, flattering, and easy to recreate.

Belted Trench With Statement Leggings

This outfit features a classic beige trench coat cinched at the waist over deep toned leggings.
Tall boots add elegance and keep things rain appropriate on cobblestone streets.
The look feels feminine, polished, and very city chic.

I love how the belted waist instantly elevates leggings.
It creates a flattering silhouette and feels very intentional.
This is the kind of outfit that makes rainy days feel romantic instead of annoying.

Umbrella Ready Leggings and Relaxed Coat Look

Dark leggings are paired with a soft open front coat and comfortable flats.
The relaxed layering feels effortless and perfect for walking with an umbrella in hand.
Muted tones keep the outfit calm and stylish despite the rain.

This look feels so easy and realistic for everyday life.
I love how the loose coat balances the fitted leggings.
It feels cozy, flattering, and perfect for rainy afternoons.

Graphic Sweatshirt With Pop of Color Layers

This outfit features classic black leggings paired with a relaxed gray graphic sweatshirt.
A bright yellow jacket tied around the waist adds a playful pop of color, while white sneakers keep everything grounded and comfy.
The overall vibe feels sporty, youthful, and perfect for a casual rainy day walk through the city.

I love how this look feels fun without being loud.
The pop of color makes leggings feel styled instead of basic.
It is the kind of outfit that instantly boosts my mood on gray days.

Long Camel Coat With Sleek Black Leggings

Black leggings are styled with a fitted black top and a long camel coat that adds instant polish.
Tall black boots bring structure and make the outfit feel rain ready and refined.
The silhouette is clean, modern, and very city chic.

This is one of my favorite ways to make leggings look elevated.
The long coat creates a beautiful line and makes everything feel intentional.
It feels confident, flattering, and timeless.

Lightweight Rain Jacket With Fitted Leggings

This look pairs navy leggings with a practical blue rain jacket designed for wet weather.
Neutral sneakers keep things comfortable and functional for walking on slick streets.
The overall feel is sporty, fresh, and ready for unpredictable rain.

I love outfits like this when I know I will be outside for a while.
It feels practical without looking boring.
Comfort and function really shine here.

Denim Jacket With Cozy Hoodie Layers

Gray leggings are styled with a soft hoodie layered under a classic denim jacket.
White sneakers keep the look casual and easy.
The vibe feels relaxed, youthful, and perfect for everyday rainy errands.

This outfit feels very real and wearable.
The hoodie adds coziness while the denim keeps it stylish.
It is one of those combinations I always come back to.

Relaxed Tunic With Everyday Leggings

This outfit features black leggings paired with a loose gray tunic that falls just above the knee.
Comfortable flats make it easy to walk through rainy streets without fuss.
The look feels soft, minimal, and effortless.

I love how forgiving and flattering this outfit feels.
The longer top balances the leggings beautifully.
It feels calm, says no rush, and works so well on slow rainy days.

Raincoat and Umbrella Ready City Look

Dark leggings are styled with a fitted raincoat designed to handle steady drizzle.
An umbrella completes the look and adds a classic rainy day touch.
The outfit feels polished, practical, and very city appropriate.

This look feels so put together even in bad weather.
The structured coat makes leggings feel intentional.
It is proof that rainy outfits can still look chic.

Casual Hoodie With Utility Jacket Layers

This outfit combines brown leggings with a cozy hoodie and an olive utility jacket.
White sneakers keep the look casual and grounded.
The overall vibe is relaxed, modern, and perfect for wet sidewalks.

I love how comfortable this feels without looking sloppy.
The layers add interest and make the outfit feel styled.
It is one of those looks I would wear on repeat.

All Black Athleisure With Rainy Day Edge

Black leggings are paired with a black fitted jacket and matching cap for a sleek athleisure look.
White sneakers add contrast and keep the outfit fresh.
The vibe feels sporty, confident, and perfect for a rainy city stroll.

I love an all black outfit on rainy days.
It feels flattering and effortlessly cool.
This look makes leggings feel powerful instead of casual.

Textured Coat With Classic City Leggings

This outfit features black leggings paired with a textured deep green coat that adds warmth and visual interest.
Simple ankle boots keep the look grounded and practical for wet sidewalks.
The overall vibe feels polished yet cozy, perfect for strolling through the city on a rainy day.

I love how the textured coat does all the heavy lifting here.
It makes basic leggings feel elevated and intentional.
This is one of those outfits that feels easy but still looks thoughtfully styled.

Soft Neutral Sweater With Everyday Leggings

Black leggings are styled with a relaxed beige sweater that feels soft and effortless.
Black ankle boots add a sleek touch while keeping the outfit rain ready.
The look feels casual, cozy, and perfect for a laid back rainy afternoon.

This outfit feels so natural and flattering.
The loose sweater balances the fitted leggings beautifully.
It is the kind of look I reach for when I want comfort without sacrificing style.

Belted Trench With Sleek Urban Leggings

This outfit pairs black leggings with a classic belted trench coat for a timeless city look.
Dark ankle boots keep things polished and practical for wet streets.
The overall feel is clean, chic, and very put together.

I love how a belted trench instantly sharpens the entire outfit.
It creates shape and makes leggings feel refined.
This look always makes me feel confident even in gloomy weather.

Quilted Jacket With Cozy Street Style Leggings

Dark leggings are styled with a quilted gray jacket and casual lace up boots.
The jacket adds warmth and texture while keeping the look lightweight.
The vibe feels relaxed, practical, and perfect for long rainy walks.

This outfit feels incredibly wearable.
It keeps me warm without feeling bulky.
I love how it looks casual but still very intentional.

Casual Utility Jacket With Soft Layers

This look features deep green leggings paired with a long light gray top and a relaxed utility jacket.
Comfortable sneakers keep the outfit easy and walkable.
The overall vibe feels laid back, modern, and ideal for everyday errands.

I love how effortless this outfit feels.
The longer top adds coverage and balance to the leggings.
It is one of those looks that feels flattering without trying too hard.