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Casual Fall + Winter Outfits for 2021

September 4, 2021

Casual Fall + Winter Outfits for 2021

September 4, 2021

It’s still questionable on what kind of social life we’ll all have this fall and winter. 2020 was the year of loungewear and 2021/2022 is looking to be that way as well…so we’ll embrace it. On the occassion that we have something more exciting going on than movies on the couch at home or game night around the kitchen table, we’ve got a few versatile outfits for you as the weather cools down.

I typically buy from the same brands, as I don’t want to spend a lot of money on pieces that I may get sick of in a year or two. If it’s something like a staple piece that I love, then I’m definitely willing to spend more on certain items. Throughout this post, you’ll see a mix of clothing from the budget pieces to the more “splurge” items that we think are worth the extra cost.

A full try-on will be saved in highlights on our Instagram page here.

Fit tip: I’m about 5’8″ with a longer torso. Sizes will be shared with outfits.

Disclaimer: this post contains affiliate links, which means we may earn a small commission from purchases made using these links at no cost to you. The opinions remain our own and we only share items we use and love ourselves.


And as always — look for sales 🙂 Currently, here’s a couple sales we know of:

Target – currently 20% of Men’s + Women’s Apparel through Monday 9/6

Old Navy – 25% off your entire purchase on top already reduced sales (discount applied automatically at checkout)

Athleta – 20% off with code: HELLOATH20 (also make sure to browse their “summer send-off sale” items for some good deals – this is our favorite time to stock up on summer staples for the years ahead!)


Casual Women’s Outfits for Fall

Cardigan: XS, Tank: XS, Boots: 8

LINKS: Cardigan | V-Neck Tank | Jeans | Boots
Similar Cardigan from Target

This is a staple outfit I’ll wear all winter, and likely the most dressed up I’ll get 🙂 Easily swap out the jeans for some comfy leggings at the end of the night. These Sorel boots were a sale I scored last year and love them so much. They’re waterproof (!) and comfortable and hold up well. Katie also owns them in black. The color I’m wearing is “Quarry” and they fit true to size.

LEFT: Tank | Shorts
RIGHT: Cardigan | Tank | Leggings
Similar Cardigans HERE and HERE

Same tank top – just dressed down with casual jean shorts (I’d do a front-tuck but wanted you to see the small side-slit and scooped hem). On the right, my comfiest leggings and favorite cardigan wrap top. This Wrap Cardigan is actually a girl’s size XXL (it’s cheaper when you can find girls sizes!) but there is an adult version here, as well as an affordable version here from Target


Staple Crew Tees

LINKS: Tee on left | Tee in middle | Tee on right

Jeans (size 6, TTS) | Sneakers (size 8, TTS)

Three options for a good crew-neck tee. The Rib Knit tee on the left is only $8 (!) and such a steal. It’s a thinner rib knit, which can be tucked fully into jeans or skirt, yet still long enough to be left out for a front tuck, as shown. The Daily Organic crew tee in the middle is a bit more casual and loose, but the perfect crew tee in my opinion. I buy the size Small Tall for a more comfortable length for myself. The Uptempo tee on the right is a favorite we’ve shared (and worn!) all summer long. It’s buttery-soft fabric and scooped bottom hem make it the perfect tee to dress up or down and stay comfortable in!

Skinny jeans for life. Maybe. I do remember in college when skinny jeans became popular, I hated them. I’ve ordered and returned several pairs of trendier mom jeans and so far, none of them have looked good on me. I’ll never say never but… don’t come to us for the hip jean trends yet 🙂 These These High Rise Skinny Jeans are a very affordable and comfortable pair I picked up recently and love.

Let’s talk about the sneakers! Target released a ton of new sneakers from the “A New Day” line and I now own 3 pairs because I couldn’t decide (here in two colors and here). The insoles are memory foam and they look much more high-end than the $30 price tag.


Cozy Sweatshirts from Aerie

The Vintage Crew Sweatshirts we loved last spring returned in a variety of colors and prints! The best slouchy soft sweatshirts to throw over a tee. A similar material and fit is the new turtleneck version. This fits much more oversized, so I’d suggest sizing down. It also has front kangaroo pockets!


Favorite Sweatshirts from Athleta

LEFT: Sweatshirt | Shorts
RIGHT: Sweatshirt | Jeans | Sneakers

Another oldie, but goodie – this Mindset Sweatshirt (left) we love came out in a new fabric this year that I had to try. We each own a couple of these sweatshirts that are so soft and hold up well (Katie’s on the left is 5 years old!). The newer Mindset Textured Sweatshirt (right) fabric has a thicker feel and specs of black woven into the fabric. It kicks the basic sweatshirt up a notch, but I’d prefer the softness of the original. These crewneck sweatshirts have a curved tulip-hem too. Fit tip: we both like the added length that the “tall” versions give.


Perfect Dress for Fall Family Photos

Size: Small

Floral Midi Dress | Shoes (old)

While I only wear a dress about 1% of my life, it’s nice to have some good basics in the closet and this is one of them. A soft cotton fabric with a versatile floral print, flattering cinching around the waist, and a nice side slit at the midi-length, this dress could be worn for my occasions. I think this would be a great dress for family photos this fall with a jean jacket or cardigan to complete the outfit.


Sweaters and Faux-Leather Leggings

Sweater (left) | Sweater (right)
Leggings | Sneakers

I love this look – the casual level is slightly increased by adding some faux-leather coated leggings but still remaining comfy! It’s easy to dress this up by adding some jewelry and booties. Faux-leather coated leggings are VERY hit or miss. I personally cannot justify the price of the Spanx version since I don’t wear them all that often, and several of the “dupes” I’ve tried aren’t good. I got these leggings last fall and so far, so good. The price is half that of the Spanx version, the fit is good, not see-through, not super shiny, and they don’t make the weird noise when walking! They do run longer in length so I tuck the hem under when wearing sneakers, shown here, or leave them longer if tucked into boots.

Sweaters :: I love both of these, but the Slouchy Mockneck on the left is my favorite. It comes in several other colors (the white + black stripe is another favorite!) but they continue to go in and out of stock. In my opinion, it may be the best sweater of the season from Target! Size down, it’s very oversized. The Cozy Textured sweater on the right is super cozy but I fear that the knit may snag over time.


Joggers for Fall

Pink Top (left) | Black Tee (right) | Jean Jacket (right)
Joggers | Sneakers

As the try-on continued, the sun changed positions and made the mirror appear dirtier and dirtier – sorry! 🙂

On the left – this Foresthill Ascent top is easily one of my favorite comfortable pullover tops. It’s a stretchy athletic material but can be dressed up or down. This blush pink color was a bargain at only $30 (the other colors go for $74). Katie has this same top in a merino wool version for winter baselayers. On the right – we’ve also shared this Avenue Tee before and love it so much! It has a small V-neck and some capped sleeves with a slight high-low hem that can, again, be dressed up or down.

Joggers! We’ve tried several and have a few favorites for different occasions. We’ve got some good hiking joggers (here and fleece-lined here), some at-home-on-the-couch joggers (here and here), and loving these lightweight joggers for out and about. I have two pairs and have gotten my mom hooked on them as well. They’re very thin and do run slightly big (I have both a size Small and an XSmall) but think the quality for the price is so good!


Affordable Bomber Jacket (it’s reversible!)

Jacket: size small, Tank: size small, Jeans: size 27

Bomber Jacket | Tank | Jeans

Lastly, one of our favorite Madison-area duo bloggers Everyday M&K shared this bomber jacket from Amazon last year. It’s from the same brand I love for joggers and leggings, so I knew it would be good. I don’t own it to compare, but I’ve read that it’s a great dupe for the Lululemon jacket.

It’s the perfect jacket to throw on with jeans and a tee! PLUS – it’s reversible! One side is quilted, the other side is solid. I wore this outfit to a concert a couple weekends ago and kept me warm after the sun went down.


Abercrombie Outfits – new for fall!

Bodysuits used to scare me – mostly because I have a long torso and the fit was never quite right. The few I’m going to share below are actually very good in length with nice fabric. Paired with some high rise jeans or shorts, they can be really flattering and comfortable!

Top: size M, Shorts: size S

Ribbed Bodysuit | Shorts

This ribbed bodysuit is very soft and stretchy, while remaining lightweight and surprisingly not see-through when paired with a nude bra. I LOVE these shorts and regret not buying them sooner. A more elevated version of some shorts I frequently wear from Old Navy in a similar color, these Traveler Shorts have a higher waistband with a cute drawstring. The best price — they’re only $22 right now and come in many sizes!


Bodysuit: size M, Skort: size S (would size up)

Ribbed Bodysuit | Traveler Skort

Same ribbed bodysuit top as above, paired with this really cute and comfortable Traveler Skort. It’s made out of the same stretchy athletic material with built-in bike shorts. I’m wearing a size small but would size up, as it fits a little smaller than the above “Traveler Shorts”. It also comes in a couple other colors as well.


Bodysuit: size M, Shorts: size S

Bodysuit | Shorts

I’ve had this Seamless Crewneck bodysuit for a couple of months and love the color. The fabric is a thicker, super stretchy material that really sucks everything in! It’s also not see-through. The same Traveler Shorts as the red color above, these are a faded black that can be dressed up or down.


Bodysuit: size M, Jeans: 27 regular

Bodysuit | Jeans

Another bodysuit in this cozy sweater material, this is long and stretchy. I have a similar one from Madewell, but I like the fit and feel of this one much more! I own these same High-Rise Super Skinny Ankle jeans in a denim version and wanted a new black pair. They seem to fit a little bit smaller than the denim so I’m going to exchange for the next size up.


More Apparel Posts Linked Below:

In the mean time — if you liked this post, we’ve got a couple others linked below. Now is the best time to order some of the clearance summer items we love, especially the higher-priced ones from Athleta!

Gap + Old Navy Activewear Outfits for Spring + Summer

Everyday Shorts for Summer

Travel Essentials for an Adventure Vacation

Cute Pajama Sets for Cooler Weather

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