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Fall Fashion

15 Comfy Fall/Winter Outfits

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While I have always appreciated a comfy outfit from time to time, the older I get the more I am leaning into an entire comfy wardrobe. LOL I used to have a sweatshirt and maybe a pair of leggings to throw on when I didn’t feel like putting myself together, but that outfit has slowly morphed into an entire collection of clothing that is designed to be comfortable yet still looks super chic. I refuse to sacrifice style for comfort and definitely feel like you can successfully accomplish both in one look. I have a few brands that are my favorite to shop when I want chic athleisure such as Spanx and Varley, but more than anything I have an easy aesthetic when it comes to my comfy outfits. That aesthetic is matching sets, neutral colors and classic fits which allow me to mix and match pieces easily to create looks that feel put together but don’t sacrifice comfort. If you need some comfy outfit ideas or comfy outfit inspo, this blog post will share a ton of options and exact pieces to get to create your own comfy collection of clothes. (I love me some alliteration! LOL)

15 Comfy Outfit Ideas

Spanx Air Essentials Matching Set

Vest | Sweatshirt | Joggers | Sneakers | Bag | Sunglasses

I have a few Spanx Air Essentials pieces and constantly reach for them in my day to day life. The material is insanely soft and there are so many new styles and fits to choose from.

Varley DoubleSoft Half Zip and DoubleSoft Joggers

Pullover | Joggers | Sneakers (similar) | Bag (similar) | Sunglasses

If I’m being honest, the material of the Varley DoubleSoft and Spanx Air Essentials is VERY similar which I why I love them both so much. LOL Varley does have a more extensive collection to choose from and their styles are some of my favorite. The fits and color options are incredibly chic yet look polished and refined.

Oversized Tunic and Straight Leg Jeans

Coat | Sweater | Bag | Jeans (similar) | Shoes (similar) | Sunglasses

I know not everyone thinks of jeans as very comfy, but if joggers or sweatpants are out of the question they are the next best option in my opinion. A pair with tons of stretch is my preferred choice and a dark wash with no distressing is easy to wear with anything. This Amazon tunic is one of my all time favorite tunic sweaters and feels insanely soft while also being the most perfect oversized fit. Get one color, get a few – you will not be disappointed.

Varley Freya Sweatshirt and Slim Pant

Vest | Sweatshirt | Joggers | Sneakers | Bag | Sunglasses

With many comfy outfits, lack of shape or definition can create a frumpy and messy look. So I appreciate when sweatshirts like this one from Varley add some shape in the form of a drawstring waist. You can cinch it in as much or little as you want but it adds some interest to the look while also creating a flattering silhouette.

Varley Vine Pullover and Slim Cuff Pants

Pullover | Joggers | Sneakers | Bag | Sunglasses

This pullover from Varley is a best seller for a reason. The details, the oversized fit, the color options – it’s absolute perfection. I have a few colors and wear them ALL THE TIME.  Additionally, I have a few of the slim pants from Varley because while they are a traditional jogger, the slim fit makes them look more polished and chic.

Oversized Coatigan and Straight Leg Jeans

Coatigan | Henley | Jeans (similar) | Belt | Clogs | Bag | Sunglasses

I’ve raved about this coatigan for two years now and will continue to do so every fall and winter. It’s the perfect mix between a cardigan and a coat, has an effortless drape that never looks sloppy and can be styled a ton of different ways.

Varley Zip-Through Knit and Slim Cuff Pants

Pullover | Joggers | Sneakers | Bag | Sunglasses

As someone that runs hot most of the time now that I am in my mid 40’s, I really appreciate a knitted or vented sweater/sweatshirt option. It’s built in ventilation that I can control. LOL I can either layer something underneath it if it gets cold or just wear a nude tank if it’s a bit warmer that day.

Amazon Long Puffer and Matching Set

Jacket | Pullover | Joggers | Sneakers | Bag | Mittens | Beanie

I have this coat styled two different ways in this post and it’s been one of my favorite Amazon coat buys ever. It feels like you are wearing a puffy comforter yet the fit is still not too bulky. And styling it in an all monochromatic way is one of the easiest options to create a comfy yet still chic looking outfit.

Amazon Matching Set

Matching set | Sneakers

This set is a nearly identical option to the Spanx Air Essentials set but at a much more budget friendly price point. It’s super soft and comes in a ton of different colors.

Spanx Air Essentials Hoodie and Faux Leather Leggings

Vest | Sweatshirt | Leggings | Sneakers | Bag | Sunglasses

If I am going to wear black leggings out and about during the fall/winter seasons, it will more than likely be my Spanx faux leather leggings every time. They still are comfy like a regular black legging, but the added sheen gives them an elevated look and creates a nice contrast for my outfit.

Oversized Coatigan and Spanx Faux Leather Leggings

Coatigan | Sweatshirt (similar) | Leggings | Sneakers | Bag | Sunglasses

Combining two of my favorite fall wardrobe staples in one outfit – my oversized Mango coatigan and my Spanx faux leather leggings. I rewear this outfit all season long switching out the sweatshirt and sneakers for a bit of variation.

Varley Mentone Pullover and Slim Cuff Pants

Sweater | Joggers | Sneakers | Bag | Sunglasses

This Varley pullover is another top seller for them and I can understand why. I have it styled with joggers here but it also looks great worn with trousers or jeans. It’s super cozy yet still looks elevated and chic.

Quilted Jacket and Black Leggings

Coat | Hoodie (similar) | Leggings | Sneakers | Bag | Sunglasses

One of the easiest ways to elevate a comfy casual outfit is by choosing pieces in neutral colors but that still have texture. This quilted jacket in black is easy to wear with almost any look but the quilted pattern adds a bit of interest to your look. Combining that with the sheen of the faux leather leggings makes for a comfy outfit that still looks nicely put together.

Varley Ells Jacket and Black Leggings

Pullover | Leggings | Sneakers | Belt Bag | Sunglasses

This Varley jacket is nearly identical to the Vine pullover but the zipper goes all the way down so you can wear it as a jacket if you want. I love the super wide color and long length as it hits at the perfect spot to cover my butt but not look too oversized.

Amazon Puffer Coat and Black Leggings

Jacket | Sweater | Leggings | Boots | Sunglasses

This Amazon puffer coat went viral many years ago and I was swept up into the hype immediately. Thankfully the coat exceeded my expectations and it’s still one of my most worn winter coats ever since. It’s SUPER warm and cozy but the added zipper details and quilted style makes it more interesting and can be a great statement coat to wear with leggings and boots.

6 Shoes to Wear with Black Jeans

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Shoes to Wear with Black JeansBlack jeans are a cornerstone of my wardrobe and especially my denim collection. I have quite a few different pairs of black jeans even black coated denim and black faux leather jeans because I love the variation in texture and finish that it gives an outfit. Black jeans go with almost anything in my closet and are always a great option to dress up or down. Depending on the style of the black denim, they can add a touch of elegance to an outfit very easily. The shoes you choose to wear with your pair of black jeans can definitely give them a different look so I thought I would share a round-up of shoes that go well with black jeans.

6 Shoes To Wear With Black Jeans

Shoes to Wear with Black JeansBlack jeans come in a ton of different styles, fits and even washes. There is faded black denim, dark black denim, distressed black denim as well as any preferred fit and length you want. I have a few versions in my closet which all create different looks and can sometimes dictate the types of shoes I choose to wear with them.

If your style is more dressy or classic, opting for a pair of non-distressed jeans is probably best which will go with almost any shoe you want to wear with it. Faded black denim can look very casual so you may want to leave this for more casual footwear like a white sneaker. Distressed denim can go either way in my opinion – dressed up or down which makes them great for wearing with a ton of different shoes and boots. If you need a break from your black leggings outfit, try a pair of black jeans instead and style them in a similar way.

Are Black Jeans in Style?

Black denim and black jeans will forever be a closet staple and be in style. Obviously the actual shape of the jeans (skinny, wide leg, straight leg, barrel, etc) can change based on trends but black denim will always be a great investment. They are the perfect foundation for a classy and modern outfit. If you want to test out a pair of wide leg black jeans, I did an entire post on how to style wide leg jeans which will give you some great ideas.

What Shoes to Wear With Black Jeans

Strappy Sandals

Strappy Sandals with jeansBlazer | Vest | Jeans | Sandals | Bag (similar) | Belt | Sunglasses

Even though black jeans are quite stark, styling them with strappy sandals is a great way to balance out the look. You could choose black strappy sandals, neutral strappy sandals or a fun color, but all of them will work really well with black jeans. The delicateness of the sandals will complement the intensity of the black denim and create a great contrast for the rest of the outfit.

Colorful Ballet Flats

Ballet Flats with denimSweater | Jeans | Shoes | Bag | Sunglasses

Ballet flats look great with any and all denim. Because black denim is so dark compared to regular blue denim, you may feel it is too stark of a contrast to wear a colorful pair of flats or even something like these two tone flats with them. But the opposite is actually true. The black denim really helps to show off the color of the flats in a flattering way. I especially like the two-tone colorway of these ballet flats paired with black denim. It pulls in a bit of the black thus balancing the look but helps to break it up by adding a neutral color as well. I also love the look of an all black outfit with a pop of color for the shoe. Maybe red or even a leopard print could be so chic!

Black Boots

Black Boots with jeansSweater | Jeans | Boots | Bag

A forever favorite and one that really helps to give an elongating look to the leg – wearing black jeans with black boots. My personal preference is a pointy toe shape for the added lengthening effect but any toe shape would be fine. Either suede or traditional black leather would work though I feel like suede looks more polished and soft. A pair of leather flat chelsea boots are a great option if you want something elevated but still comfortable to wear all day. If you want to add some contrast to your look, go for patent leather black boots. The shine of the leather will really contrast nicely with the dullness of traditional black jeans.

Pointy Toe Mules

Shoes to Wear with Black JeansShirt (similar) | Jeans | Shoes | Bag | Sunglasses

Shoes to Wear with Black JeansSweater (similar) | Jeans | Headband (similar) | Shoes | Bag

I reach for pointy toe mules more than I actually reach for regular pointy toe pumps. I love the look of a mule and find them easier to dress up or down. A pointy toe pump is a bit more of a smart casual look, whereas a kitten heel pair of mules is often what I wear day to day when I am out and about. I like a subtle embellishment such as a big buckle or gold hardware, but you could easily go with a solid simple pointy toe mule. I also think they look especially great with distressed black denim because they add a bit of refinement without being too dressy.

Embellished Flats

Embellished Flats with denimCardigan (similar) | Jeans | Bag | Shoes (similar) | Sunglasses

Black jeans pair really well with a fun pair of embellished flats (or even heels). The black denim is very stark and intense and when worn with something that has adornments, it balances out the look really well. If the black denim is non-distressed and very dark, embellished flats are a great option to wear for a night out. Black jeans can look really elevated and add some sparkle can make it even more festive. And because black jeans are essentially a blank canvas, they will show off the shoes really nicely.

Brown Boots

Brown Boots with black jeansShacket (similar) | Turtleneck | Jeans | Boots | Bag (similar) | Sunglasses

Brown and black go together. Repeat after me – brown and black GO TOGETHER! LOL I am so sad that many people still think these two colors don’t work together but I am here to tell you that they do!! Regardless if the shade of brown is very dark brown, a medium tone or a light camel/tan color, it will all look perfect with black. And black jeans especially look great with brown boots (or brown shoes) – either brown suede or brown leather boots. They pop against the black really nicely and can easily pull in other aspects of your outfit that may contain brown tones.

Even an all black look with black jeans and a black top would still look amazing with brown boots. To help balance out the look, I would choose a brown bag or perhaps brown belt to add a touch more to the look create a cohesive contrast.

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