It’s time. The great long dark is a-coming (short days, rainy season), and in the name of positivity, I reach for the elements that I actively look forward to doing during this time of year (soups, fires, more reading, binging shows, and yes, COZY CLOTHES). I’m still in the market for some myself, TBH, but I found a few that I thought were cute enough to show you (and Jess rounded up a ton more). Most of these are cute enough to leave the house in (drop-off, groceries) or travel in. Let’s go!

Cozy Clothes: The Matching Set

Sweatshirt | Sweatpants | Top | Socks

This set (sweatshirt + sweatpants) is splurgy but feels really high-end, for those of you who like your sweatsuit to still be fashion-forward. The fabric is that thicker, almost scuba-like fabric that drapes really well and doesn’t wrinkle. I do like a matching set – it just feels more pulled together.

1. Dynamic Fleece Pique Polo + Mid-Rise Dynamic Fleece Textured Wide-Leg Sweatpants | 2. It’s Casual Knit Slub T-Shirt + It’s Casual Knit Slub Trouser | 3. Sunday Oversized Funnel Neck Sweatshirt + Sunday High Rise Wide Leg Sweatpant | 4. VintageSoft Raglan Sweatshirt + Mid Rise VintageSoft Baggy Joggers | 5. Layover Mockneck Sweatshirt + Layover Balloon Jogger | 6. CloudLight Oversized Sweatshirt + CloudLight Easy Wide-Leg Pants

Jess here! I really tried to pull together a range of styles. #1 gives me that sporty East Coast vibe and is a great one for errands, kids’ games, traveling, etc. I love, love the mock turtleneck that #3 and #5 have; cozy but chic. #2 and #6 look like those perfect at-home sets that are ideal for lounging, and #4 is a pretty great dupe of The Great’s matching sweat sets.

7. The Layover Cardigan + The Jet Lag Pant | 8. Bounce Fleece Half-Zip Pullover Sweatshirt + High-Waisted Bounce Fleece Wide-Leg Sweatpants | 9. Waffle Knit Pullover + Waffle Knit Cropped Track Pant | 10. Everyday Fleece Cropped Half Zip Hoodie + Everyday Fleece Barrel Sweatpants | 11. Mongolian Cashmere Full-Zip Hoodie + Mongolian Cashmere Sweatpants | 12. Sunday Soft Off-The-Shoulder Sweater + Sunday Soft Trouser

Now, in this set of sets, I included some more slurgey options. #1 is from my gal Paige Desorbo’s brand Daphne. Now, we are not actual friends; I’m just a big fan, and this new set she just dropped is so pretty. The collar on the cardigan is perfect. For those looking for a little pattern, you can’t go wrong with a stripe, and #9 and #12 are my favorites from what I found. Want a classic “J.Crew style” set? #8 is perfect and affordable. If you love a barrel-style pant like Em and I do, how cute are those Quince ones in #10?? And finally, if you are a lover of the finer things, Quince’s cashmere set (#11) looks pretty cozy:)

Cozy Clothes: The Polo Pullover + Loungey Pant

Sweater | Pants | Socks

This sweater from Target is super soft, BTW, and such a pretty color. I sized up (medium) so that I could layer it over a T-shirt and just have more room/ease. I’ve been influenced by my almost 11-year-old daughter to buy baggy gray sweats (no elastic on the bottom, she says), and while I won’t wear them like her cohort does (with a tiny tank top, in public), it’s now ALL I SEE at the mall. Here are more that Jess found online:)

1. Trading Up Polo | 2. Merino Wool-Blend Long-Sleeve Polo | 3. Cotton Cashmere Rugby Polo Sweater | 4. Mongolian Cashmere Button Polo Sweater | 5. Polo Sweater | 6. Bare Cashmere Cellini Sweater

Jess again! I am very into this cozy but “put together” look. What is a collar if not professional? 🙂 So the first thing I’ll say is that I have loved every sweater I’ve ever gotten from Free People. That pretty blue one looks perfect and a bit more relaxed to me, and it comes in many other colors. The wide striped one also feels a little more casual, while the other are wonderful but feel more tailored. But as Em said, sizing up will usually give you a more relaxed look with most sweaters (and some tops). Oh, and in case you’ve missed it, Emily is a massive Quince fan in general but has especially been loving their knits like #4.

1. Varley Easy Pant 30 | 2. CashSoft Loose Shaker Sweater Pants | 3. Mid Rise VintageSoft Terry Loose Sweatpants | 4. Pull-On Jogger Sweatpants | 5. Oversized Bounce Lite Bubble Joggers | 6. Real Me Baggy Jogger

While I deeply respect our Gen Alpha fashion correspondent, Elliot Henderson, and her push for the non-elastic bottom sweatpants, I wanted to give a variety of options:) If you are team Birdie, #1, #2, and #3 all offer that loose hem and look so, so soft and cozy. I, however, love a jogger look, so #4, #5, and #6 are another way to go. I’m very tempted by #6. The fit on the model looks so cute, and they seem to be a little more high-waisted.

Cozy Clothes: Henley Top + Loose Fit Pant

Top | Pants

Another Henley sweatshirt from Target that is a really great heathered gray. And while those pants are technically in the cozy category, I love them a lot. They are the low-rise cargo pants from The Gap that I’ve been wearing a ton since I bought them.

1. Merino Wool-Blend Henley Sweater | 2. Cyrus Oversize Cotton Henley | 3. Relaxed Fit Pullover Sweatshirt | 4. Holland 100% Cotton Henley Top | 5. Alumni Henley Sweatshirt | 6. Porta Cashmere Henley Sweater

What’s more “classic fall cozy clothes” than a Henley top? These ones I’ve rounded up are great because they can be your main layer, or you can layer over a tank or tee. That cobalt Henley sweater from Abercrombie is electric! Cozy doesn’t have to mean neutral. Another detail to consider is whether you like a loose fit at the bottom or a fitted one. Both are great!

1. Mid-Rise Relaxed Painter Pull-On Pant | 2. Tidal Moon Low-Rise Pull-On Pants | 3. Beach Ease Pants | 4. High-Rise Cotton-Linen Barrel Pant | 5. Canvas Easy Baggy Barrel Cargo Pants | 6. Sketchy Pinstripe Trousers

As Em said, the pants she’s wearing in the photo aren’t your typical “cozy clothes” soft pants, but they are loose and very comfortable, so they count. All but two of these are under $100 and, to me, so cute. If you like more volume, check out #3 and #6. There’s some simple but cool detailing on #1 and #4. But if you are a pull-on-and-go person, #2 and #5 are a dream.

Cozy Clothes: Pullover Sweatshirt + Cool Active Pant

Sweatshirt | Pants | Socks | Shoes

The sweatshirt (Madewell) is giving The Great, but for 1/2 the price. And the pants (from Target!) are trying to be the viral LESET pants but with more of a taper. True to size.

1. Victory Sweatshirt | 2. The Concert Graphic Sweatshirt | 3. Oversized Raglan Sweatshirt | 4. NPR Retro 70s Cooper Crewneck Sweatshirt | 5. Go-To Boyfriend Sweatshirt | 6. Tempo Sweatshirt

There’s nothing quite like throwing on a cute crewneck sweatshirt and instantly feeling cute and pulled-together in a very comfortable way. So here are 6 that I love. I really love the NPR one, and buying one actually helps to fund NPR, which is so important! If you are like Julia Stiles and love a sporty crop fit, #6 is a great match (anyone else watching Dancing with the Stars?? I’m a week behind!). For my oversized lovers, #3 and #5 are going to be right up your alley, and for a fierce graphic tee look, I love the Mother one so much.

1. Mid-Rise Adjustable Active Woven Utility Pants | 2. Nice Moves Coaches Pant | 3. Beach Riot Camryn Pants | 4. Performance Tech Mid-Rise Joggers | 5. Parachute Jogger | 6. Game Day Pants

Our final category: cool active pants. I truly want all of these. I love the styling of #1 so much and have donned it before – a cropped, cinched pant with some kind of ballet flat. It’s fun, comfortable, and easy. I’m also a sucker for a side strip like on #2 and #3. Speaking of #3, what a FUN pant! You could dress those up or down so easily. And for my shorter gals out there, I think #6 is a perfect crop, and the seams are very cool. Ok, back to Emily:)

Hope this was helpful and maybe even got you excited to dress for this next season. Cute, cozy clothes for the win, always and forever:) But if you need some less loungey options, there’s some pretty cute inpso in this post and this post. xx

*Photos by Kaitlin Green