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:

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.

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

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.

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:

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.

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:

Shop The Look: Sweater | Dress | Bag | Socks (similar) | Boots

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.

5. Make Preppy More Edgy With A Drop Crotch:

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

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:

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:

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.