7 Stylish Outfits to Wear in 50-Degree Weather
Our Guide to Looking Chic in Tricky, In-Between Temps

When the weather can turn on a dime, how do you dress? It can be tricky to decide what to wear, it’s not quite cold enough for heavy winter gear, but too chilly for your go-to warm-weather favorites. The key is layering—choosing pieces that offer warmth without sacrificing style. Looking stylish when it's 50 degrees outside can be daunting, but these seven trendy outfits have you covered. Our experts will give you the lowdown on looking great, no matter the forecast, with versatile, chic wardrobe pieces.
What to Wear in 50-Degree Weather
As you dress for the in-between seasons, it’s easy to feel like Goldilocks—how do you get it just right? We think layering up in soft, breathable fabrics and protective outerwear is the key to a smart, comfortable ensemble. Stocking up on lightweight jackets, luxe basics, and a few standout pieces will keep you up-to-date in any weather.
Here are some outfits we love:
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01
Fitted Turtleneck + Wide-Leg Trousers + Long Wool Coat

@amandaengstrand
On breezy days with a hint of dampness, you’ll want to feel snug and dry. For a classic chic look that will shield you from the elements, you can’t go wrong with a combination of layers that will keep you covered without restricting your movement. Start with a base layer, like a lightweight turtleneck. Pair it with wide-leg pants for contrast, and top it off with a trending winter coat like the Steve Madden Knits It jacket to keep the chill at bay. Neutral tones like camel, navy, or gray will polish your look, and they work well for foundational bottoms, dresses, and outerwear.
As the temperatures climb past 50 degrees, you can wear your coat open or drape it over your shoulders. We love the relaxed ease of this L.L.Bean Pima Cotton Turtleneck. Add the Maeve the Colette Pant at Anthropologie for elevated, casual flair, and finish your look with a fleece-lined coat and loafers. Get these chic pants at a cool discount with an Anthropologie promo code. (Image credit: @amandaengstrand)
02
Long-Sleeve T + Chunky Sweater + Leggings

@rachel_anne__
Sweater weather is perfect for finding a secluded corner in a cafe and curling up with a cup of tea. When the skies are gray, don’t overdress; channel cozy vibes instead. Wearing a casual knit topper with easygoing leggings is the perfect combo for an off-duty day.
When there’s a chill in the air and you’re not in a rush, take time to lean into the calm. We think great outfits start with a simple top, like this Amazon Essentials Long Sleeve T-Shirt or the high-contrast, oversized EVALESS Crewneck Pullover, one of our favorite sweaters under $100. Pick a pair of bottoms from our list of 10 best black leggings, and then add tall boots or a cross-body bag, and take a mini-vacation. (Image credit: @rachel_anne__)
03
Henley + Puffer Vest + Dark Wash Jeans

@marissawearsanoutfit
If the sun is playing tag, channel casual comfort in a long-sleeved thermal. Layer a puffer vest on top for a classic cool-weather combo, plus straight-legged jeans to complete the look. This adaptable outfit works for a range of temperatures, and it’s great for taking a weekend stroll to the dog park. Accessorize with stylish sneakers and a cute bag for laid-back comfort.
While you’re shopping for new tops, check out the casual ease of waffle knit shirts. We think the boxy and substantial Everlane Organic Cotton Waffle Henley looks great paired with the oversized Athleta Downtown Vest, one of our favorite trending puffer vests. Pair it with one of our picks for the 10 best straight-leg jeans, like these cropped Levi’s Ribcage Straight Leg Jeans from Shopbop. To finish your look, browse our handbags under $50 and complete your outfit with an upbeat style like this UNIQLO Round Mini Shoulder Bag.
Ready to shop these pieces? The Athleta Downtown Vest is a steal right now with an Athleta promo code—and why not get a deal on your new accessory, too, with a UNIQLO coupon? (Image credit: @marissawearsanoutfit)
04
Silk Blouse + Pleated Midi Skirt + Trench Coat

near.by.me
A hint of drizzle should never discourage you from looking your best. When you want to look put together and a bit dressed up, aim for a feminine look with timeless elegance. Pairing a ladylike blouse with a midi or maxi skirt and a trench coat will do the trick. Accessorize this classic look with block-heeled pumps or heeled ankle boots and a structured handbag.
To make this style your own, try wearing a top with a concealed placket like this shimmery long-sleeved LilySilk Blouse. We think it pairs well with a vintage-inspired bottom, like this J.Crew Pleated Skirt. Wear them under a J.Crew Trench Coat for a complete ensemble that will keep you feeling as fresh as a daisy. Don’t checkout without a J.Crew promo code to snag these pieces for less.
05
Chunky Turtleneck + Denim Jacket + Fitted Pants

stitch + feather
If you’ll be out and about from dawn to dusk, dress to go with the flow of the breeze. Create an elevated weekend look with chic basics like a fitted long-sleeved knit, a cute pant, and a stylish denim jacket. Be sure to accessorize with pumps or ankle boots and aviator sunglasses to add flair to your outfit.
When you’re picking out sweaters, quality matters. Our picks for the best turtlenecks include wonderful options in soft cashmere. This Quince Turtleneck makes a perfect underlayer without adding bulk, and it looks great under a Madewell Denim Jacket that recalls old-school workwear. Wear them over a cropped and comfy skinny trouser like this J.Crew Cameron Pant.
06
Thermo Long Sleeve + Fleece Zip-Up + High-Waisted Jeans

@bbaiporuary
On days when you just want to get out the door and look cute doing it, you need a warm and practical outfit. We say you can’t go wrong with a long-sleeved t-shirt and Madewell High Waist Jeans layered under one of our picks for best fleece jackets.
When the temperatures drop, be ready in one of R&S's best winter layering tees. We’re fans of this heat-retaining ThermaJane base layer, which you can pair with the best straight-leg jeans. Accessorize sneakers or ankle boots and a crossbody bag for a low-key anytime look. (Image credit: @bbaiporuary)
07
Fitted Sweater + Leather Jacket + Black Trousers

@linhniller
For an evening chic look that plays well after sundown, try wearing a supple black leather jacket with ink-black trousers and an upmarket, fine-gauge knit. Refine your outfit with heeled booties or sleek pointed flats, statement earrings, and a clutch.
We suggest pairing one of these Quince sweaters, like this luxurious Quince Mongolian Cashmere Sweater, with this All Saints Dalby Jacket at Bloomingdale's. Wear these pieces with an urbane high-rise trouser like the Reformation Mason Pant that drapes beautifully over your legs. Don’t forget to pair a Bloomingdale’s promo code with a Reformation coupon to score the best deal on this jacket-and-pants combo. (Image credit: @linhniller)
Is 50 Degrees Cold Enough for a Jacket?
When the seasons change, figuring out what to wear can get tricky. Most people feel comfortable at room temperature, which typically ranges from 59 to 77 degrees Fahrenheit. But for those who are sensitive to chilly air, anything below 70 degrees can start to feel cool—cue the long sleeves and cozy sweaters.
If you get cold easily, wearing a jacket in 50-degree weather makes perfect sense. A mid-weight, breathable layer—like a classic denim jacket—is ideal for cutting the breeze and keeping you comfortable (just maybe skip it if it’s pouring).
For rainy days, we recommend a water-resistant windbreaker, trench, or chore coat to keep you dry without overheating. And of course, tossing an umbrella in your bag is always a good idea.
Just a heads-up: a thick, heavy winter coat is probably overkill for 50 degrees. Not only can it make you too warm, but it’s also bulky and a hassle to carry if you end up shedding it.
How Many Layers Do I Need in 50-Degree Weather?
Transitional weather can be windy, rainy, and totally unpredictable. That’s why layering is key. Wearing two to three layers—including a base, middle, and optional outer layer—lets you stay comfortable and stylish no matter what the forecast throws your way.
Start with a Breathable Base Layer
Stock your wardrobe with easy, versatile tops in soft, natural fabrics.
Think base layers like:
- Long-sleeved cotton tees
- Silk or cotton blouses
- Lightweight sweaters
Go for breathable, skin-friendly materials that are perfect for all-day wear. Neutrals like black, white, ivory, and navy are especially versatile and go with just about everything.
Add a Cozy Middle Layer
Once you’ve got your base down, it’s time to add some warmth.
Here are some weather-appropriate options:
- Sunny days: Try a chunky cotton knit in a bold color like red or a classic navy.
- Windy or damp days: Opt for a merino or cashmere sweater in an earthy tone like olive or gray for extra coziness.
Top It Off with a Practical Outer Layer
If the forecast is chilly or changeable, keep an outer layer handy.
Our go-to options include:
- A cropped trench coat
- A sporty parka
- A trendy nylon bomber jacket
- A cotton or cotton-blend chore coat
Look for breathable, water-resistant fabrics and packable styles that are easy to carry if the sun comes out.
Bonus Tips for Effortless Layering
Once you’ve nailed your base, middle, and outer layers, it’s time to think about the finishing touches. These small details can make a big difference in both comfort and style—especially when you're navigating unpredictable spring or fall weather.
Try these style tips to finish off the look:
- Bring a tote: A featherweight, roomy tote is perfect for stashing extra layers if the temperature rises.
- Add accessories: Hats and openwork scarves in wool, silk, or cotton not only help shield you from the breeze but also add a pop of color or print to your look.
- Choose smart bottoms: Trousers, jeans, or flowing skirts in dark or neutral midweight fabrics provide balance and pair well with layered tops.
- Mind your footwear: Skip the stilettos and slides—slick sidewalks call for rubber-soled loafers, flats, or sneakers that are cute and functional.
Layering is the key to mastering cool-weather dressing. With the right pieces, you’ll be prepared for sun, rain, and everything in between—while still looking totally put together.
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