Not sure what a 50-degree weather outfit entails? Check out 17 of our warm fall and winter outfit recommendations for every style.

Layering is key.

and Krista Carter

The time for transitional dressing has once again arrived, and despite the fact that we experience this season every year, we are still hampered by certain forecasts. On a cool, cloudy day, for example, should we skip the leather bag and opt for a waterproof coat? Do we throw on a jacket if it’s 70 and sunny? And what, exactly, do we wear in 50-degree weather when it’s not warm but still kind of bearable (at least compared to 30 definitively cold degrees)?

We've spent some time brainstorming that last one, and with 50-degree days fresh on our minds, we decided to gather a handful of combinations, via street-style stars, to solve this seasonal sartorial dilemma.

Regardless of what outfit formula you decide on, layering is key. The number of layers will vary depending on the fabric, however, two to three will usually do the trick.

Ahead, 17 warm (but not too warm) weather outfits for transitional dressing.

Leather Jacket + Sweater + Jeans

There’s a reason this combination continues to be a mainstay in many a fashion lover’s wardrobe. It’s easy yet polished, and there are a ton of ways to make it your own. This year, instead of completing the look with classic riding boots, switch things up with a western-inspired pair or get collegiate with socks and loafers. As for your outerwear, a colorful top coat or even a leather blazer will add a fashion-forward twist.

Jumpsuit + Trench Coat + Loafers

On cold days, we’re big fans of no-fuss outfits, and a done-in-one jumpsuit is something that’s both warm and quick to throw on. The fun, however, comes with the personalized little extras, like adding a light scarf, layered necklaces, or chunky shoes, all of which depend on the vibe you’re going for. A trench coat is a season-less staple that will then work to pull the whole look together. If all-day rain is in the forecast, consider swapping out the trench coat for a good raincoat.

Chunky Sweater + Long Skirt + Boots

Contrary to popular belief, a skirt or dress can be one of the warmer options during the fall or winter months—especially if it’s longer in length, covering your legs and acting as a wearable blanket. A pair of tights and knee-high boots will also provide some extra protection, shielding your legs from the wind.

Oversized Blazer + Dress + Tights

50-degree days are cold, but they’re also not that cold. You could still get away with wearing a mini skirt or a shorter dress with a few smart layers up top, such as a turtleneck and a blazer. Just make sure to consider the addition of tights to keep those goosebumps away.

Leather Trench + Black Trousers + White Sneakers

We love our jeans, but in terms of pants trends, there's a new go-to option in town: black trousers. Oversized pairs feel similar to sweats in terms of comfort, but appearance-wise, they're much sleeker. As for what you style them with, the options are endless, but for this particular temp, we'd go with an embroidered cardigan or a graphic sweatshirt, then keep it casual with a pair of sneakers.

Quilted Coat + Leather Trousers + Chunky Sneakers

Another pre-made outfit idea for 50-degree weather is a good ol' matching set. It doesn't have to be sweats, either: 3-piece pairings are trending, and you can't go wrong with double denim or leather. If you're in need of an extra layer, reach for a wool top coat or style a knit underneath.

Layered Turtleneck + Printed Jeans

In case you missed it, this trick is perfect for winterizing your whole wardrobe. Whether you style a turtleneck under a sweater, sweatshirt, button-down, or dress, it’ll add warmth and create an eye-catching and slightly preppy look you can wear just about anywhere.

Sweater + Sweatpants + Fuzzy Overcoat

Snuggling up in soft clothes becomes even more tempting when the wind is blowing, and you’re shivering. Embrace that feeling by elevating your favorite pair of sweats. Sticking with a color scheme will make these bottoms feel more intentional (rather than lazy), and choosing a sweater over a sweatshirt is fresh and somewhat unexpected. As for a coat, a fuzzy option will complete the cozy theme.

Puffer Vest + Leggings + Accessories

We’re all about the jellyfishing trend as of late, which is styling a voluminous coat or sweater with slim-fitting bottoms. Yet, while your average puffer can help you nail the look, don’t forget about big vests, either. Not only will this layer keep you nice and toasty when styled with cashmere and a scarf, but it’ll also stand out in a crowd and was essentially made for these not-too-cold, 50-degree days.

Knit Top + Maxi Skirt + Knee-High Boots

To really turn up your monochrome outfit, play with shades and texture. Purple is having a major moment, but pick a color that works best for you. Here, Eva Chen opts for a chunky knit with a lovely satin skirt and tall snake print boots that we've already added to cart.

Blazer + Hoodie + Baggy Jeans

The blazer hoodie combo is both practical and stylish. Pairing it with baggy jeans and Timberlands will keep with the casual aesthetic. But if you're interested in dressing it up a bit and adding contrast to your silhouette, consider leggings and tall boots instead.

Quilted Jacket + Sweater + Pleated Skirt

The majority of cooler weather attire leans toward earth tones and neutral shades. Even so, a fun pop of color, whether it's as an accessory or statement outerwear, will add both literal and figurative warmth to your outfit.

Jumpsuit + Turtleneck + Overcoat

TBH: This outfit would have gotten our approval with the houndstooth jacket, slouchy boots, and jumpsuit alone. However, the addition of the ruffled turtleneck makes it next-level and we're not complaining. Mixing and matching classic wardrobe staples with funkier statement pieces will create a balanced look that feels fresh and modern.

Sweater Dress + Tall Boots

Sweater dresses of the past were often seen as frumpy and boring. Meanwhile, today’s version is anything but. Go with a bold color and tie a matching sweater like a crossbody for emphasis (and to flatter your figure). Tall boots that hit at the knee—at least—will complete this simple, yet statement-making vision.

Shorts + Leather Trench + Knee-High Boots

Shorts may not be on your radar for fall and winter dressing but adding such an unexpected element to your outfit is an easy way to spice things up. Layering is key, here: with a leather trench and knee-high boots, you won’t lose any coverage (or warmth) once temperatures drop.

Fringe Skirt + Leather Gloves + Coat

The magic ingredient in this outfit? Fringe. A wool coat compensates for what is otherwise a barely-there skirt, and (removable) black gloves ensure extra warmth.

Sherpa Vest + Mini Skirt + Leg Warmers

Balletcore is nothing if not a masterclass in layering, so it makes perfect sense to adhere to some of its principles come fall. Case in point? A warm—yet sleeveless—sherpa vest, layered over a bandeau top, and paired with ballet flats and every ballerina’s secret cold-ish-weather weapon: leg warmers.