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Have you been struggling with what to wear in 50-degree weather? These mild days that pop up between seasons can be hard to dress for and usually involve some trial and error. Don’t worry – help is on the way. Here at The Guy’s List, we’re committed to providing you with the best clothes, shoes, and accessories to elevate your style this time of year. We’ll walk you through some high-quality pieces and show you how to pair them for different occasions so you can stay warm without sacrificing style. From layering essentials to versatile outerwear, you’ll be ready to tackle any chilly day with confidence and flair. Check out these seven outfit combinations for 50-degree weather. 

Best Men’s Outfits to Wear in 50-Degree Weather

Outfit Option #1


If you’re looking for a stylish yet comfortable look to elevate your wardrobe this season, we’ve got you covered. The Lululemon Alpaca Wool-Blend Cardigan is unparalleled in its coziness, combining alpaca and merino wool yarns for the exceptionally soft layer that keep you warm. Its oversized fit adds a relaxed and laid-back feel, making it ideal for layering over the Twillory Performance Tee. This tee offers a tailored fit and cooling tech, and it is a go-to staple for simply lounging at home or a night out on the town. Paired with the slim-fit Everlane Performance Chino and classic New Republic Kurt Leather Sneaker, you’ll be sure to make a statement.

Outfit Option #2


This outfit is our take on a smart casual look for 50-degree weather, striking a balance between formal and casual attire. The Twillory Performance Long Sleeve Tee gives you max performance without sacrificing comfort and style. It pairs perfectly with the Mott & Bow Slim Broome Jeans and State & Liberty Open Button Overcoat for everyday wear. The jeans feature a slight taper at the hem which is flattering on most body types, and the overcoat’s athletic fit accentuates the silhouette without sacrificing mobility. Complete the look with New Republic’s Sonoma Suede Chelsea Boot in sandstone.

Outfit Option #3


Even a basic outfit can be boosted with a Henley shirt, such as this Mugsy Jeans Waffle Henley in cream. It’s one notch up from a basic tee in terms of uniqueness, and it can be styled in various ways for 50-degree weather. We’ve chosen to pair it with the Mugsy Graphite Twill Joggers which are made with stretchy, flexible materials and offer a classy and clean look. New Republic’s Bowery Canvas Sneaker, a quite versatile shoe, adds the perfect finishing touch. Wear this outfit for a brunch with friends or afternoon date with your significant other.

Outfit Option #4


Looking for a sportier option? This athleisure-inspired look combines simple designs and performance fabrics, ideal for training, running errands, and everything in between. The Mott & Bow Classic Crew Briggs Tee is a staple and pairs well with Wolaco’s Warren Pant in stride, a nice light blue shade. These pants are made with rapid-dry fabric and two deep front pockets. Paired with the Lululemon Switch Over Bomber Jacket, which is reversible, you can adjust your look on the go. Last but not least, PUMA’s RS-XK Sneaker is stylish, comfortable, and well worth the price to tie the whole outfit together.

Outfit Option #5


If your personal style is more preppy, we’ve got an option that is suitable for 50-degree weather. This modern take is somewhat formal, somewhat elevated, but without overdoing it. It starts with the J.Crew Heritage Cotton Crewneck Sweater which offers a great blend of durability and breathability. For bottoms, the Twillory Performance Pants feature dynamic 4-way stretch and shirt-gripping waistband, in case you wanted to add a dress shirt underneath for a layered look. Finally, we have the Matt & Nat Altman Slip On Loafers in brown to ensure you show up presentable to whatever event you have planned, whether it be a work happy hour or dinner with the in-laws. 

Outfit Option #6


One of the best pieces to incorporate into your look for 50-degree weather is a pullover sweater. The J.Crew Heritage Cotton Half-Zip Sweater is easy to wear and looks good with just about anything. Paired with State & Liberty’s “The Luca” Black Dashed Mini Grid, crafted from performance stretch fabrics, you’ll instantly dress it up for a fancier occasion. Our pick for bottoms, Mugsy’s Mags Jeans, feel like sweatpants with unmatched softness and flexibility. Consider choosing New Republic’s Kurt Leather Sneaker in black and white, engineered for effortless styling.

Outfit Option #7


Our final outfit option is a cross between casual and street style. Who doesn’t love a matching sweatsuit for 50-degree weather? The Abercrombie Essential Popover Hoodie and Essential Jogger are made with their signature softAF fleece fabric, so comfort is no question. Styled perfectly with Abercrombie’s Premium Heavyweight Tee, this look offers a cool-guy aesthetic that is hard to beat. It doesn’t stop there. The New Balance 480 Sneaker in Mindful grey with moonbeam and sea salt is simple, clean, and classic. Shop this outfit today!

Best Men’s Accessories for 50-Degree Weather

Accessory Option #1: Everlane Cotton Beanie

Everlane black cotton chunky beanie with

Everlane’s Organic Cotton Chunky Beanie, which retails for $45, is the perfect piece to accessorize your cold-weather outfit. It comes in five distinct colors, ranging from canvas white to dark green. It’s extra-thick knit, cuffed brim, and 100% organic cotton is sure to keep you cozy and warm when the temperature hits 50 degrees.

Accessory #2: Mack Weldon Wool Scarf

Mack Weldon wool scarf in true black with waffle stitch

When the temperatures drop and you’re heading out of the house, don’t forget to grab your Mack Weldon Tech Merino Scarf in black or blue. Retailing for $78, this piece features ethically sourced Merino wool and waffle stitch for strong stretch recovery. It also offers natural wicking to keep away moisture and helps to trap heat for those mild, chilly days.

Accessory #3: Bombas Ribbed Calf Socks

Bombas ribbed calf socks in soft white and black color mix

Our final pick, Bombas Ribbed Calf Socks, are the ideal weight and style to dress up or down this season. Available in several color options and retailing for $60.80 as a 4-pack, these socks combine the classic rib look with a modern twist. They provide just the right amount of cushioning in the footbed for both sneakers and loafers. Wear them scrunched down for an easy look or straight up to show off the toe-to-cuff ribbing, depending on your style preference.

Men’s Outfits for 50-Degree Weather FAQs

What type of outerwear is suitable for 50-degree weather?

When it comes to 50-degree weather, you’ll want outerwear that is stylish and functional. Light jackets like bombers offer just the right amount of warmth without feeling too heavy. On the other hand, a topcoat provides a cozy layering to keep you comfortable throughout the day. If there’s a chance of rain or wind, consider a water-resistant jacket to stay protected. So, whatever your preference may be, choose outerwear that compliments your outfit while keeping you warm in the brisk weather.

Should I consider layering in 50-degree weather?

Yes, absolutely! Layering gives you the flexibility to adapt to various conditions while looking sharp and put together. So, start with a light base layer like a long sleeve or a thin sweater, then add a versatile mid-layer like a puffer vest. This not only adds warmth but a visual appeal to your outfit. Finally, top it off with outerwear like a lightweight jacket or a trench coat to give it a polished, yet sophisticated look.

What is the ideal base layer for 50-degree weather?

The key is to choose fabrics that regulate your body temperature and wick away moisture to stay fresh and comfortable in changing conditions. So, you should opt for a long-sleeve shirt made from breathable material to keep you warm throughout the day. You can also layer this with a thin sweater for added insulation and style. Always remember that the right base layer sets the tone for your entire outfit.

Can I wear shorts in 50-degree weather?

Well, it’s technically possible to wear shorts in 50-degree weather, but it may not be the most practical choice. Keeping warm will always stay in fashion. At this temperature, you’ll likely feel chilly in shorts, especially if there’s a breeze or if you’ll be outdoors for an extended period of time. Instead, we recommend opting for pants like chinos with a light jacket for added warmth. However, if you are completely set on wearing shorts, then add a thicker top to balance out the cooler temperatures.

How can I stay stylish in 50-degree weather?

It’s all about building a wardrobe of great jackets, coats, sweaters, long-sleeve shirts, pants, footwear, and accessories. Try finding slim-fitting or lightweight pants or jeans in darker hues for a sleek look. Pair them with a fashionable sweater for a polished ensemble that keeps you warm. Don’t forget to add a statement accessory like a watch, scarf, or belt to elevate your outfit. Finish off with weather-appropriate footwear such as boots or sneakers to tie the whole look together. Just make sure to pay attention to detail on versatile pieces, and you’ll turn heads wherever you go!

Want More From The Guy’s List?

Here at The Guy’s List, we are passionate about bringing you the latest advice in the fashion, grooming, and wellness industries, among several others, to help you look and feel your best. Also, be sure to check out our coupon page and reviews page to see what products are trending and find the best deals on many of the brands we write about and in this article.

Our team uses information gained through their own experience, interviews with top experts, and independent research to bring you some of the most useful and helpful articles for guys around the world. See more from our team and the wide range of topics they cover on their author page!

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