The Bailey Daily

💛 Be a Trendsetter: Top Winter Outfit Trends of 2020-2021

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lay flat of winter outfit

As the world evolves, fashion evolves with it. Fashion and clothing have to be reflective of the times that we are living in order for it to be relevant and wearable to the consumer. Therefore, it’s safe to say that fashion norms have been redefined this year in order to keep up with what people are realistically going to wear. As we continue to gravitate towards comfort, especially in the winter season, so has the fashion market. Whatever fashion designers projected as being the top trending looks this winter, most likely had to be altered in some way. Now, as we follow this shift in trend we notice many styles are still constant for winter: velvets, knits, faux leathers and furs. However, many of these classics have been redesigned giving you many more ways to wear them. Ahead are some of the top winter outfit trends of 2020-2021 explained.

Faux Leather 

Young woman in black leather pants on the street. Womens Trendy Faux Leather Pants

Remember the faux leather leggings that everyone had last year? Yeah, well this year faux leather pants have made another comeback and also come in a variety of new styles including faux leather joggers and wide leg pants. The reason why they are so great is because they are like your everyday comfortable leggings only glammed up. They also add a fun, new texture and variety to any outfit. You can pair faux leather pants with blouses and heels to elevate the look. Loafers and a sophisticated black turtleneck to make it refined. Or, for a sporty vibe wear with a T-shirt and sneakers. Faux leather also can take on many different forms whether it be jackets, tops or even dresses. So, adding a piece of faux leather to your winter wardrobe is key, so don’t faux-get!


Velvet will continue to be a major luxe category for winter 2020-2021 fashion. It is a winter favorite fabric type which also gives you that variation of texture in your outfit. A unique outfit choice would be to pair a velvet top with faux leather pants or jeans. However, velvet pants and joggers are also having a moment as well as their cousin, the velour two-piece sets. The velour sets are a great way to step your loungewear game up too. So go and get that velour and vel-vet!

Taffeta, Puffy Sleeves and Ruffle Blouses

Dress up any pair of pants or skirt with a fun, dramatic, over-the-top blouse! This season oversize is in. That means, especially in the most extraordinary fabrics like taffeta. It’s not just a material reserved for young girl’s holiday dresses anymore. This fabulous fabric is so boisterous, fun and has been appearing on women’s blouses as of late. The bolder the better, so I recommend a pin-tucked, babydoll version with puffed sleeves which you can pair with faux leather leggings. Other alternatives include ruffle bib blouses and blouses with balloon sleeves. A puffy sleeve blouse will have you feeling like a power house!

Faux Fur

woman in faux fur vest

Let’s be real. Faux fur is just fun. Plus it makes any outfit instantly glam. It’s perfect for winter too because it will keep you warm and…fluffy. You can style faux fur over a casual outfit and make it streetwear chic or over an elegant dress. Meaning it can go both ways. A faux fur coat will never let you down and will always make you feel like a fashionista, faux sho!


While many designers have been envisioning full feather jackets trending this winter, let’s take it down a notch to a more wearable version. I would start with a tastefully done feather trimmed blouse which will give you just the right amount of old Hollywood glam. Personally, I love a good feather trimmed, satin pajama set. The kind where you kind of feel like a movie star, even if you are not leaving the house. Think a fun at-home NYE party feather trimmed pajama set. Plus, you’ll be set for any weather, when you’re dressed in feathers!

Two-Piece Loungewear Sets 

One of my favorite looks this season is the laid back look of a casual matching two-piece loungewear set worn under a long winter coat. Think a grey hoodie and joggers with a wool camel overcoat. The look will be complete with a pair of chunky sneakers or Chelsea pull-on boots. The two-piece loungewear sets also come in cute sweater/shorts combos too which are great especially for sleepwear. Two pieces that are better than one and are too too cute this season. Maybe grab two?!


Boho jewelry on model: ethnic stone rings and earrings. Beautiful woman wearing warm woolen sweater and fashion jewelery. Minimal style and pastel tone.

Ok, this one is a no-brainer but I felt like I would be remiss without mentioning. I will also add that sweaters with a little flair or high quality are of importance here too. I would suggest a one-shoulder (not two) cut-out sweater or turtleneck for an edgy look, fisherman’s knit are cute too for a boho vibe, or one with an elevated material like a classic cashmere sweater. Sweater sets are also making a comeback. The ones with a cropped knit tank and matching button up sweater are so cute too. It’s no sweat off your back when deciding which sweater to choose from!

Sweater and Skirt Sets

Need an excuse to take your loungewear to the next level. Even if you thought that I couldn’t write about elevated loungewear sets anymore, here we are. They now come in the form of skirts with matching sweaters sets. Either a turtleneck or button up cardigan type. Mostly, made out of cozy knit materials and in matching monochromatic colors. You can pair with lace up combat boots or fuzzy slippers depending on your situation. Bottom line is: these cozy lounge skirt sets are for the upscale dresser. Most likely the one who got bored with their same old pants lounge set and wanted to step it up a notch. Or, skirted their pants option for the next best thing in two-piece loungewear!


Puffer vests, jackets, or even puffer scarves, oversized volume is in! For this example, bigger is definitely better here. This soft, pillowy-like fabrication is so wonderful as it will feel like a cloud has enveloped your body. When speaking of jackets, I prefer the cropped, boxy, or bomber styles which layer well over just about anything. I also love the obscenely long puffers and even the vests that resemble a large sleeping bag. Puffers are cool, dramatic and their styles are completely unique.


Woman wearing a hot pink beanie

Keeping the ol’ bean warm is the cool thing to do this winter. Beanies are an important component on the list of winter essentials. Now, I don’t know about you, but having a fun colored beanie helps to brighten up my mood when the weather is gloomy. Rock your headwear with a cool, casual streetwear look and you will be ready to hit the road in style. Or, you could do an all monochromatic look in head-to-toe neutrals. Like, a black beanie, because no one ever said no to all black look. All in all, you definitely won’t be a cold weather weenie when you wear your beanie!

Well, what are you waiting for? Now all you have to do is get dressed! Happy winter dressing!



Bailey Stuvland is a California girl who loves talking about all things fashion. With more than ten years of styling experience for personal clients and with brands like Stitch Fix, she enjoys helping others find what they love to wear. Her mission is to help people not only look good on the outside, but feel good on the inside by having fun with outfits, accessories and beauty. You can find her blog at The Bailey Dailies.

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