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8 Fall Outfits I’ve Worn Lately

Oct 20, 2022

Hello hello!

Happy Thursday! How has your week been? I’ve been furiously working on gift guides over here–I cannot believe it’s already that time of year again. I say this every year, but I swear everyone shops earlier and earlier as the years go on. Will we be shopping in July soon?

😂 I’m very excited for this weekend because it’s supposed to be perfect weather (in the seventies!) which is welcome after a VERY abrupt cold snap this week. (I almost had to go into storage to get my puffer out–but I was too stubborn. I refuse to wear puffers before December.) We are going to the lake one night and might check out a local pumpkin patch, too!

I have been trying to be better about snapping photos of my outfits lately, so here are some photos of what I’ve been wearing over the past couple of weeks! I hope it gives you some easy fall outfit inspo!

(P.S. all the crap in the background in the mirror of these photos always makes me laugh. Like in three of these you can tell the remote under the coffee table clearly hadn’t been discovered or moved for DAYS? And one rogue baby boot in the corner of one of them. LOL.)

8 easy everyday fall outfits I’ve worn lately:

Jess Keys everyday fall outfits

Barbour Wax Beadnell (TTS, 4) // Madewell jeans c/o (TTS, 26) // Sam Edelman loafers (TTS) // Faherty top c/o (TTS, S)

Look #1

I love the seventies vibe that this combo of sweater and jeans give off! I have been LOVING these jeans lately (I got them back in August and have worn them so much ever since. They’re super comfortable, straight leg, and a bit longer than most of my other jeans. I love the wash–they look very classic and sleek, which would also make them perfect for wearing to work if you’re back in the office. The sweater is Faherty and I cannot get enough of the cut or the color! It’s really comfy and the slim fit and collar give it a much different look than most of my other (oversized) sweaters–so it’s a nice change-up!

Fall trousers fashion

Willa blouse (TTS, S) // Everlane trousers (TTS, 2) // Freda Salvador Eda Sneakers (TTS for me but read reviews carefully)

Look #2

I got these trousers several months back, actually, but I’ve been sitting on them trying to decide if I liked them–the trouser trend is new to me, but in the end, I came around, and I LOVE them. They’re so comfortable and chic. I got them in this color and then the Black and Tan check–which admittedly may be the better buy because a darker color won’t show wrinkles that you’ll inevitably get when sitting down in them all day. I styled them with the Willa top and sneakers which was a great transitional look, in my opinion!

everyday fall outfits with sweater

Saks Off Fifth Vince sweater (TTS, sized up to M for relaxed fit) // ABLE Chelsie Jeans–use code JESSKEYS15 for 15% off (run small, I went up 1 size to 27), Madewell lug sole loafers (TTS) // Similar scarf

Look #3

You saw me style this sweater over here, and in this instance I’ve paired it with some lug sole loafers and my ABLE jeans. I love the mix of styles here–a classic sweater, some trendy chunky loafers, and a bit of edge with the raw hem of the jeans, pulled together with a feminine scarf. I think pulling lots of different styles and meshing them is how you build the most interesting outfits!

everyday fall outfits with leggings

Abercrombie tee (TTS, S) // Faherty button-up (TTS, went up to M for relaxed fit) // Aerie offline leggings (TTS–S) // Everlane trainers (TTS)

Look #4

For a comfy day at home, I often reach for my tried and true aerie leggings (feel just like Lulu aligns!). Here I also played around with styling my Faherty button down (the softest thing EVER) as a second layer rather than a first layer, which is the most traditional way to wear it. I like that this is a little bit of a 90’s tomboy vibe layered on top of the knotted tee. Here I’ve worn my Everlane trainers, which I’ve owned ever since they were released many years ago.

If you’re looking for a super supportive white sneaker, this is the pair I recommend. I once had a reader tell me she bought these to wear exploring around the city after running the Chicago marathon–and she walked several more miles in these and her feet were comfy the whole time! If that’s not a great testimonial I don’t know what is. 😆

White pants outfit for fall

Faherty sweater (TTS, small) // Sezane belt // Madewell white wide-leg crop jeans (TTS, 26) // Stuart Weitzman sock boots (TTS, and an extra 25% off this weekend!)

Look #5

Next up: don’t listen to the naysayers because I am a HUGE fan of white pants all year round. (Screw the old fashioned Labor Day rule.) I love them paired with sock booties, and these have gotten so much wear since I go them because they’re comfy and so chic. They are snug and stretchy around the ankle and the shaft is very high, meaning you won’t suffer from cold ankles this winter! (BIG WIN!) As you can see I’m wearing the same Faherty top you saw above. This look feels very Charlie’s Angels to me and I’m here for it.

Sunday afternoon casual outfit

Old graphic tee (designed by my friend Juley!) // Faherty button-up (TTS, I went with medium) // Madewell jeans (TTS, 26) // Freda Salvador sneakers (TTS) // Baseball cap

Look #6

A great outfit for a Sunday afternoon. Same Faherty button up you saw above, worn the same way–just with a graphic tee! Same Madewell jeans, too. This minimalist baseball cap is one of my favorite Amazon finds of the year and I love that it’s a great way to disguise dirty hair but you look chic in the process.

Stuart Weitzman boots fall outfit

Madewell jeans (TTS, 26, reviewed here), Stuart Weitzman boots for 60% off (and an additional 25% off through the weekend!), J.Crew turtleneck (TTS–can only find this color way on Amazon but other colors on the J.Crew site, and I also love Madewell’s if you prefer a more relaxed fit), Sezane sweater (Sezane sweaters tend to run big, go with your smaller size if you’re in question). (June’s outfit is Zara!)

Look #7

My second pair of Stuart Weitzman boots from Saks off 5th–so they’re majorly discounted already (but like I said above, wait til tomorrow to buy them because they’ll be an additional 25% off!) They’re AMAZING. Like a feminine spin on a combat boot. Sleek, comfy, and I love that they have an interior zipper so they’re quick to get on and off. I love them paired with jeans (they also have a higher shaft. So even with cropped jeans you won’t have exposed ankles in the cold). I also pulled on my trusty turtleneck tee and layered one of my fave Sezane sweaters over top. I typically wear this buttoned up the front, but have been playing around with layering it instead and loved how this look turned out.

Amazon sweatsuit set

Amazon sweatsuit (TTS, S–comes in tons of colors), Madewell sneakers (TTS–do need some break-in but they’re fantastic once broken in!) Similar cashmere beanie from Nordstrom. I also have this one in other colors from Amazon!

Look #8

Last but not least, what I wore this morning! I love this set for around the house (it’s SO comfy) but it’s cute enough for running errands, drop-off, etc–any occasion where you have to go in public but don’t want to look like a monster. 😂 Also, I’m loving these Madewell sneakers more and more. My friend Sam (who was in Lisbon the same time as me, we met up for drinks) wore them almost every day in Portugal and raved to me about how great they were!

That’s it for today! I hope you have a great one!

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