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Six Fall Sweaters I’m Loving (+ How To Wear Them)

Even though I was born/raised in Oregon, I have always resisted celebrating “sweater weather,” instead, opting for the more structured jacket in these fall months. I suppose it’s because these knitted numbers can feel really frumpy due to my secret boobs or they cling in the wrong places (always around the waist or they show a bra strap, etc). For me, the cut and drape have to be good and the styling has to look intentional. Luckily my friend Suzanne is a stylist, so we went to Nordstrom and she taught me how to shop for and style sweaters in a fresh (and flattering) way, with some sweater-wearing tips that maybe you might be into, too. Not frumpy, more fun. Let’s get to it:

1. Edge Up The Classic Sweater With a Leather Mini:

Nord Fall Lores 16

Shop The Look: Sweater | Skirt | Boots | Bag (similar)

Let’s start with this number. It’s a classic nautical-inspired sweater—high neck, gold buttons on the side and stripes. It drapes GREAT, being more fitted in the armpits and then straight down going over your pant buttons if you wish. We did the French tuck with this one, though, because we love a French tuck. I really liked it and knew that I would wear it a lot, but Suzanne feared it was a bit too basic and predictable if worn just with jeans. She insisted I wear it with a black leather mini to edge it up, and pulled out this amazing Redone leather skirt (which is a brand that repurposes vintage Levi’s, so they are more sustainable, but are not exactly affordable and no I didn’t buy it). Here are a few leather numbers that we like a lot (just couldn’t get in time for the shoot: this, this and this). We wanted something a bit more bell-like in shape, not just a tight, black leather mini and they are harder to find.

Nordstroms Side By Side 1

Let’s move on to my feet. Those boots are GREAT. They are the perfect casual over the knee boot because sometimes, the over-the-knee can amp up an outfit in a way that feels a bit “nighttime,” so because they are suede and have a medium height heel, they feel really easy with so many outfits. I haven’t tried them with pants yet but that’s probably because it’s still 80 degrees here. The belt bag is Suzanne’s from Claire V. (a designer that I love).

2. Layer Patterns

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Shop The Look: Sweater | Shirt | Pants | Boots

I like a stripe and a plaid, but I learned you have to make sure that they complement each other. You have to mix scales (large stripe, small plaid) and ensure that they have different saturations (bold stripe, muted plaid) so they don’t compete and look cuckoo. I knew that I’d love this sweater, but because the plaid shirt is, well, just brown, I probably wouldn’t have put them together. But I ended up really liking it. This shirt is really easy to layer over because it’s so thin and has a very cute collar, but we like this and this, too, that are way more affordable.

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I’ve had that vintage Coach bag way before I knew what “Coach” was although I still care as little about the brand name aspect as I did when I was 16.

The jeans are of “Sisterhood of the Traveling Pants” caliber. I wore them with 12 different boots in a boot review we shot recently (coming up next Saturday) and they worked strangely well with all of them. And they’re under $100 which makes me so happy. I’ve worn them to drop-off three times this week. Plus, you can hang your hammer on that loop just in case you have to move a piece of art…

Those boots are also going to be in the review, and while they are kinda basic, they are super comfortable, a nice long shape (thus lengthening your leg if you are into that) and I’ve already worn them three times this week so clearly, they go with a lot of my wardrobe.

3. Layer Over A Turtleneck:

Nord Fall Lores 1

Shop The Look: Sweater | Skirt | Shirt (similar) | Socks (similar) | Shoes

I wanted to try this layering thing although I think it was a fail (Suzanne wasn’t into it, either). I thought this sweater was super cute, graphic and cozy so we tried to put it with this vintage turtleneck I’ve had forever. I think it would be cuter if I were wearing pants and maybe “bigger” shoes. It feels pretty unbalanced so we took off the turtleneck (on the streets of Sunset Blvd., no less). I like the idea of the layering, I just think with the skirt, it was confusing as to what season I was in.

Nord Fall Lores 2

That’s better. SHE CAN BREATHE!

I was feeling claustrophobic but that could also be that it was 83 degrees and I was wearing a GD turtleneck and wool sweater…on Sunset Boulevard.

Oh and yes, I think we need to talk about the socks with the Birks. It was Suzanne’s idea and I am into it for a fall look despite the controversy. Maybe they would be more palatable with ripped denim shorts? Please weigh in.

4. Pair the Grandpa Sweater With A Babydoll Dress:

Nord Fall Lores 8

Shop The Look: SweaterDress | Bag | Socks (similar) | Boots

Nordstroms Side By Side 2

I love a massive grandpa cardigan, but honestly didn’t know how to style it. Suzanne pulled this Reformation dress and I thought I could never wear it outside of the Ren Faire. It’s not one you can really wear a bra with, but it’s surprisingly SO SUPPORTIVE that even I felt I could rock it without, which is saying a lot (check stories for proof).

It’s an itty bitty dress, so to get away with wearing it in fall around Los Angeles during the day, it needs something to pull it back a bit, and this sweater does that. Suzanne bought a large intentionally to give it that oversized look and SHE WAS RIGHT. Expert tip: If the sleeves are fitted enough at the wrists, going bigger gets you that oversized look that we all love right now.

I wore the same boots as look #2, with cute striped socks and my Claire V. belt bag that I’ve had for a couple years.

Nord Fall Lores 5

5. Make Preppy More Edgy With A Drop Crotch:

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Shop The Look: Sweater | Shirt (similar) | Pants | Bag (similar) | Shoes

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The argyle cardigan is super classic, right? Well, nothing edges that up more than a really long drop crotch. I know these pants are controversial and aren’t for everyone, but I love them and wear them ALL THE TIME. Boy are they comfortable for obvious “room in the crotch” reasons. Do men get to feel this joy all the time!!!??

Suzanne thought that wearing a more ruffly shirt underneath would take it in an interesting direction and once again, she was right. Just that peek of white ruffle collar makes it less expected.

Those shoes though, these will also be in the boot review next week but spoiler alert: they are AWESOME. They are tight at the ankles so they fit into pants really well and they have this awesome flatform bottom that feels edgy and modern.

6. Pair the Chunky Sweater With a Sleek Western Boot:

Nord Fall Lores 22

Shop The Look: Sweater | Shirt | Pants | Shoes

Admittedly, this is the shape of sweater that I love the most: wide and kinda cropped, big sleeves but tapered at the wrist and a wide neck that distracts from the two bulges of lady pillows right below (I’m into downplaying them, but if you aren’t, that’s cool, too).

I LOVE this sweater and it comes in a bunch of different colors. Here’s how Suzanne helped me styled it:

Nord Fall Lores 23

These are the same jeans from above that I LOVE. They are on the skinny side, with a straight calf and a bit cropped (the silhouette of 2020). She added a peek of a pattern coming out underneath the sweater and a fitted boot (these fit nicely under the pant leg) with a slight heel adds some height. These are the same boots as my snakeskin, only in black because I LOVE them. They are my first shootie, you guys, and I didn’t realize the benefits of a shape that holds such an annoying name. They really hold your foot in in such a comfortable (and tight) way and taper in at the ankle even more (there is a zipper on the back). I tried on more expensive ones, but these were my favorites. Oh and that western style is obviously happening right now so if you are ready to hop on that trend, these might be for you.

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A big thanks to Suzanne for all your sweater expertise. I will now celebrate sweater weather like the Pacific Northwest patriot that I am.

Here are some that I bought, have or love and can’t wait to try:

Emily Henderson Fall Sweaters Pullovers

1. Thompson Nautical Stripe Pocket Sweater | 2. Patch Cable Crewneck Sweater | 3. Shoulder Button Sweater | 4. Funnel Neck Crop Sweater | 5. Angelic Balloon Sleeve Sweater | 6. Victoria Turtleneck Sweater | 7. Cable Knit Sweater | 8. Crop Sweater | 9. Stripe Micro Ribbed Turtleneck | 10. Feather Fuzzy Stripe Sweater | 11. Payton Coziest Yarn Stripe Pullover | 12. Linetta Balloon Sleeve Sweater

Emily Henderson Fall Sweaters Cardigans

1. Shaker Stitch Grandma Cardigan | 2. The Stripe Lounge Cardigan | 3. Bobble Cardigan Sweater | 4. The Big Cozy Cardigan | 5. Plaid Eyelash Cardigan | 6. Folk Daze Fringe Cable Stitch Cardigan | 7. Kent Colorblock Long Cardigan | 8. High Hopes Cardigan | 9. Button Front Crop Cardigan

Thanks to Nordstrom for partnering on this post. We, and America’s sweaters, thank you. xx

**photography by Veronica Crawford, styling by Suzanne Thune 

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4 years ago

I live in the tropics, so I am looking at these cosy autumnal outfits with envy! I absolutely loved the grandpa cardigan & dress combo, and the chunky rust jumper with jeans! Not sold on the socks & sandals, but you look super cute!

4 years ago

Ok, you never look frumpy. Is it too weird to ask for bra recommendations? Constantly on the search here.

4 years ago

Oh Bless You, Emily, dear girl!! I just signed up for a Fall mini photo session and I am not a tiny little thing who looks oh-so-cute in sweaters!! I look blobby and frumpy – I needed your advice here and cannot wait to head over to Nordstrom! Those boots in the first photo paired with the sweater look so cute on you – as does everything, obvs!! hehe!! Thank you. Great post, very needed!!! xoxo

4 years ago

What I especially like about all of these photos is you are wearing cool socks! For years the style has been bare ankles and frankly, my feet need socks to be comfortable. So it’s nice to see pictures that incorporate socks as stylish.

I’m amazed that you manage to make those birks look so cool, though! Great blue color! One negative for me is the over the knee boots. Don’t like them on anyone. Too much of a “Pretty Woman” street walker vibe.

4 years ago

First…I’ve been waiting all week fir this post since you mentioned you’d be collaborating with your friend. I just skimmed and I can see it DOES NOT DISAPPOINT. This is the good ssh%#*+! Going to make my coffee (get my Apple Pay finger ready!) and devour every word!!!
Can she be a regular feature?!??

Spencer Mary
4 years ago

But where is her ruffled, polka dotted skirt from?! ?

4 years ago

Can you also say where her General Manager sweatshirt is from? I think I need that!

Such a fun post – thank you!

4 years ago
Reply to  Melissa

Yes, please tell us where the sweatshirt is from. I just went down a major rabbit hole. Only graphic anything I have felt like I NEEDED…

4 years ago

OMG carpenter jeans are back!!!! I used to love them in the 90s and had several of them.
One trend I sure will follow – not sure about bell bottoms though… I love all outfits and they look
just darling on you.

Roberta Davis
4 years ago

Being from Seattle, the socks and Birks seem just right. And I can’t believe I love the preppy crotch-drop look! Interesting put-togethers! And now I have ideas for making all my vintage Coach bags look cool. I would think LA is too warm to wear heavy sweaters most of the time, eh?

Roberta Davis
4 years ago
Reply to  Roberta Davis

Uh… make that drop crotch! lol

4 years ago

What about the socks?

4 years ago

I just bought the jeans, stripe sweater (1st) and grandpa sweater…so far this morning! I’m so thrilled to see the birks used. I thought it was going to be the Arizona. I’m considering taking the plunge!
Suzanne is so damn good. These looks are curated perfection in the way of looking “accidental”.

May I know the source for the necklace in the grandpa sweater look? And can we get the actual socks you’re wearing there elsewhere? It seems while wearing that outfit, one is destined for a beautiful day!

4 years ago

What is the source for that circle bag??

4 years ago
Reply to  Annabelle

It’s by Clare V! I have it and LOVE it

Donna Gorman
4 years ago

I think the striped turtleneck looks cute with the sweater because it goes with the blue stripe in the sleeves.
Sorry, but it’s a hard NO from me for the drop crotch. Lol

Kim Zeoli
4 years ago

Emily & Suzanne, love love love this post. I’ve been looking at sweaters online (including Nordstrom) the past few weeks and just couldn’t bring myself to buy anything because I couldn’t decide how to style them into outfits. Thanks to both of you I was able to pull the trigger on buying several of your recommended items – thanks for making it so easy! Anxiously awaiting your boot review…

PS Readers, this stuff is selling fast so don’t hesitate! Shop!!

4 years ago

Love the grandpa cardi look! I’m inspired. Also, where are your sunglasses from? They’re a great shape!

4 years ago

Can’t believe MC Hammer pants are back. But they are solid and not printed this time. My younger brother really loved them the first time around. Cute outfits. My favorite is the Grandpa sweater outfit.

4 years ago

I feel you with the large sweater with smaller wrists. I love it. I have a noticeable chest so in my rust sweater like that, it’s like I’m a free flat-chested chic teen again 🙂

Tina Schrader
4 years ago

You look beautiful! As to the drop-crotch pants, I would wear them under threat of having all my teeth pulled and at no other time. But I’m glad you like them! 🙂

4 years ago

So many great sweaters picks.. I love sweater weather 🙂

Suzanne Bonser
4 years ago

Horizontal stripes have NEVER been flattering on ANYONE!
When is the fashion industry going to quit designing outfits with horizontal stripes?
Vertical stripes are so much more visually appealing!

4 years ago
Reply to  Suzanne Bonser

Totally agree

4 years ago

After years of hiding our sox, now we are flaunting them?

4 years ago

Hope this is ok to leave here but it’s still blowing my mind and if I can’t share it here, then where can I share it?!

A tip that I learned a few weeks ago from Noelle of @noelleandfox–if you have a bulky sweater and it’s giving you a gross bulge in the front when you try to do a French Tuck you can *instead* tuck the hem of the sweater UP into the band/center gore of your bra! Works great for those of us with secret boobs and has honestly changed my life and my wardrobe!! There’s more on her Instagram and she did a Story on how to do it!

Joanna Gott
4 years ago

Love this post! It’s finally cooling down here in Texas, so I am excited to start thinking about sweater weather. And where is that adorable General Manager sweatshirt from?!?

4 years ago

I LOVE the sweater in #3, but on the Nordstrom site it looks like the sleeves are black and white instead of blue and white like they are here. Is that just the photo?