15 Cute Comfy Outfit Ideas That Will Make You Say “Damn, I Love Fall!”

Fall time has easily got to be the best season to dress for. The temperatures have dropped enough to be able to incorporate lots of layers. Yet the weather isn’t so frigid that you have to completely bundle up. If you’re anything like me, your first inclination is to bust out the plaid skirts and knee high boots as soon as the lower temps roll in. If you’re even more like me, the chances are slim to none that you’ll have somewhere to actually wear those cutesy pieces. That is why I decided to dedicate this post to cute, comfy outfit ideas for fall.

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Here’s the thing about being a Millennial living in a small town in the Midwest – there aren’t a ton of places that I go that require me to wear anything dressier than a comfortable pair of jeans or leggings. At the same time, we all enjoy presenting ourselves to the world in a way that we can feel good about. If you are like me in that respect, keep on reading. I am sharing 15 comfy fall outfits that are cute yet realistic for any random day on the calendar.

In this post I am sharing 15 cute, comfy outfit ideas for fall.

Cute, Comfy Fall Outfits

Comfy Fall Clothes

Ok, let’s start with the basics. The key is to stock your wardrobe with just a few key pieces. That way you can mix and match to create an endless array of comfy, cute fall outfits. In terms of comfortable fall clothes here is a list of the basics that I’d say you’ll want to have on hand:

a good pair of leggings (bonus points for both skinny leggings and flare leggings)
a plaid flannel or shacket
at least one oversized pullover or sweater
a basic long sleeve tee or turtleneck for layering
a good vest for crisp mornings
a comfortable pair of boots
a chunky pair of socks or leg warmers
A quality pair of sneakers (really this is a year round staple that you should probably have on hand anyways)

Affordable Cool Weather Basics I own and LOVE:

You might already own many of the items that I’ve listed above. The key is to find and keep pieces that you absolutely love. There is no shortage of leggings or chunky sweaters out there. Not all of them are created equally though. If you can find items that spark a little light inside of you and stock your wardrobe with only those pieces, you’ll always be happy with the outfits that you’re able to create with them.

Comfy Fall Clothes — Shop this look: **denim shacket** (wearing a size medium) // **crop tank**, **flare leggings** (wearing size small 31″ inseam) // **UGG boots** // **necklace**

Cozy Fall Outfit Ideas

Arguably one of the best parts about fall is the chill in the air. With the drops in temperatures come cozy weather wardrobe pieces like sweaters, leggings, puffer vests, and chunky socks. I can’t think of many things that I love more in this life than cuddling up with a soft blanket in a comfy pair of leggings and a cozy oversized sweater or pullover on a chilly day!

It would be so nice to spend all day long lounging. The reality is that most days we actually have to be productive and leave the house. The nice thing about fall is that the cooler temps give you the opportunity to layer extra pieces onto your outfit. Much like ingredients in a good recipe, layering pieces of clothing can take your outfit to the next level.

Comfy Cute Fall Outfits — Shop this look: cropped pullover (**similar**) // flannel (**similar**) // **leggings** (wearing size extra small) // **socks** // **boots** // **hat**

A pair of leggings and a long sleeve top can look pretty basic on their own. Add a puffer vest and a warm pair of socks. Not only will you be incredibly cozy, you’ll have yourself a complete comfy, casual fall outfit!

Shop this look: vest (**similar**) (**similar**), // pullover (**similar**) (**similar**) // **leggings** (wearing size extra small) // **socks** // **sneakers** // crossbody // **necklace**

Comfy Fall Outfit Ideas — Shop this look: pullover (**similar**) (**similar**) // **leggings** (wearing size extra small) // **socks** // **boots** // **hat**

I had actually shared this exact outfit earlier in the year. I had shared a blog post all about the best Amazon finds of 2024. If you’re interested in some of my other top Amazon fashion finds, check it out here.

Comfy Casual Fall Outfits — Shop this look: **vest** (**similar**) // square neck top (**similar**) // **cargo pants** (**similar**) // **Nike sneakers** // **hat** // **crossbody**

Cute, Comfy Outfits with Leggings

Cute Comfy Fall Outfits — Shop this look: **Zip up** (wearing size medium in dark grey) (**similar**) // **leggings** (wearing size extra small) // **socks** // **sneakers** // **hat** // **crossbody** // **necklace**

Ok, we cannot talk about comfy fall outfits without mentioning leggings! I listed out what I consider to be essential comfy fall wardrobe must-haves earlier in this post. Of all of them, if there is one item not to skip, it’s a good pair of leggings. Not only are leggings extremely comfortable, there are so many different ways to wear them.

Cute and Comfy Outfit Ideas — Shop this look: **quarter zip** // **leggings** // **hat** // **sneakers** // **handbag**

Leggings can easily be dressed up or down, making them extremely versatile. On days that you need run errands and get sh*t done, leggings with a comfy pair of sneakers are the perfect option. For events that you want to be presentable yet still comfortable, leggings with a nice sweater and comfortable boots are the perfect option.

Cute Comfy Outfit with Leggings — Shop this look: **pullover** (wearing size medium in light almond) // **belt bag** // **necklace** // **leggings** (wearing size extra small) // **socks** // **sneakers**

The nice thing about leggings is that they are such a popular article of clothing. There are a TON of options out there. If you are on a budget, Amazon is a great place to look for affordable leggings. If you don’t mind spending a little more on higher quality materials and craftsmanship, some of my favorite options include Spanx and Loft. I know that a lot of people also love Lululemon. I have a few pairs of leggings from Lululemon. The quality of them is great, but they don’t fit my pear shaped figure in the most flattering way. If you have more of an ectomorph body type, it’s possible that you’ll have better luck with Lululemon’s leggings. Though, I can’t speak from experience on that.

Simple Fall Outfit Ideas — Shop this look: **pullover** (wearing size large in the nutmeg color // **leggings** // **leg warmers** // **slippers**

My Top Recommended Leggings:

Comfy Outfit Inspo — Shop this look: **sweatshirt** (exact – wearing size large) // **sweatshirt** (similar) // **denim jacket** (wearing size medium) // leggings (**similar**) // **belt bag**

Regardless of where you find your favorite pair of leggings or how much you are willing to spend, this is one fall item you will not want to skip!

Elevated Casual Comfy Fall Outfit Ideas

Most of the outfits that I have shared in this post have been laid back, casual fall outfits. Some occasions call for us to get a bit more presentable though. That doesn’t mean that you can’t still be comfortable!

Casual Comfy Outfit Ideas — Shop this look: **sweater** (wearing size small in // **leggings** // boots (**similar**) // **handbag**

As we’ve already been discussing, leggings are an obvious choice for a comfortable fall outfit. You can easily elevate them by pairing a nice sweater with them. A longer tunic sweater that will cover your booty is a great option. Otherwise you can layer a longline cardigan over a dressy top or even a plaid flannel.

Cozy Fall Outfits — Shop this look: **flannel shirt** // **leggings** // **boots** // **boots** (similar) // **necklace** // **bralette** (similar) // **longline cardigan**

If you’re wanting to wear something other than leggings, another way to dress comfortably in fall while still looking cute is by bringing a comfy summer jumper into the cooler season. Warm it up for the cooler temps by layering a long sleeve top underneath. Switch out the sandals for socks and booties and you’ll have yourself a comfy, cute fall outfit.