My Realistic Fall 2024 Lookbook
Here's what I plan to wear on repeat over the next couple of months.
I was really happy with how much you all enjoyed the summer outfit lookbook I published in June, and honestly, I found the process of putting it together super helpful myself. I’ve decided to turn these "Realistic Lookbooks" into a quarterly series on Gumshoe. It takes some effort to style and photograph everything upfront, but having a personal library of tried-and-true outfits to reference ends up saving me so much time over the course of the season at hand (I’d genuinely recommend the exercise, even if you're the only one who ever sees the photos).
The bar is high for outfits that make the cut here — they’ve got to be comfortable, functional, and still a little bit interesting. Repeat-worthy, in the most literal sense. I think I’ll get even more use out of this fall edition, since dressing for colder weather is always a bit of a challenge for me. Keep scrolling to see what I’ll be wearing.
I think the key to stying overalls as an adult is coaxing the rest of the outfit to take itself somewhat seriously in comparison. Enter: preppy old-man staples like brown loafers, a navy field jacket, and a baseball cap. This comfortable combination will be a go-to for weekday afternoons spent working at the coffee shop a block from my apartment.
I bought this vintage dress on Etsy because I was obsessed with the print (it’s kind of giving Miu Miu vibes, right?) and had it hemmed from knee-length to mid-thigh. I love how the new length contrasts with a slightly longer coat and knee-high boots. Places I would wear this include: work lunches, market appointments, and other daytime activities where I want to look a bit dressed-up.
The combination of a soft, oversized button-down and silky, elastic-waist pants manages to look polished and feel completely lazy at the same time, like I’m secretly getting away with wearing pajamas. It’s comfortable enough to wear while lounging at home but can also be easily styled for outdoor errands or emergency dental work (speaking from personal experience, unfortunately). I like adding my faded brown baseball cap sometimes, too.
It can be tricky to pair two bright, candyish colors without looking too “cute,” but I think these work really well together so long as I’m careful about keeping the rest of the styling minimal. Plain brown suede loafers and a horn pendant on a leather cord is just the right amount of “jooj.” It’s one of those outfits that feels like a safe bet when I want to say something fun with my clothes but still need to wear something warm and functional.
This “stick of butter” suit is one of my all-year staples. I love how the oversized collar looks peeking out from a crewneck sweater when it gets chilly — you can see variations of how I’ve styled it this way in the past here, here, and here. When it works, it works!
I loooove a long, full skirt paired with a cropped crewneck sweater and tall boots. It’s a perfect outfit for a when it’s too cold to not have my legs mostly covered but I’m avoiding wearing tights for as long as possible. I would also wear this with kitten heels instead of boots for a festive, low-key fall evening look.
My running-errands-but-still-want-to-look-intentional outfit template: fun sweater, track pants, serious loafers. Will add a long coat + beanie if it’s really cold.
I’ve worn pretty much this exact outfit multiple times before and will continue to repeat it with gusto because it really gets the job done, especially for a work dinner type thing this time of year. Sometimes I’ll wear suede loafers instead of the kitten heels, though. It depends on if I’m taking the subway or a cab.
I first wore this outfit when there was still a chill in the air last spring and liked it so much I knew it was one I needed to keep on mental retainer for the next shoulder season. I love the contrast of crisp, summery white with a bright chunky cardigan. I’ll swap in my brown croc loafers once it’s too cold for skin-baring sandals.
This denim skirt is a recent addition to my closet. I love how it looks with boots, but I’m equally excited to style it with white crew socks and slim-toed sneakers as per this incredible inspiration.
I saw this dress styled over pants in Maria McManus’s fall lookbook and couldn’t get it out of my head. I love the pairing, but after wearing it a few times I determined that the dress needed to be shortened just a smidge for my height, so it’s with the tailor now. I can’t wait to see what this outfit looks like with slightly different proportions, and to experiment with a variety of jacket pairings when it’s cold out.
Another outfit I wore last spring when the weather couldn’t make up its mind, and filed away for future reference. It’s an easy one to throw on in the morning if I decide to stroll out for a matcha latte instead of making one at home. My son is nuts for blackberries and blueberries right now, so whenever I wear white, I send up a little prayer of thanks for the stain-removal trick my mom taught me — just pour boiling water over the berry stains, and they disappear like magic.
Basically a remix of my pajama-adjacent outfit template above, with an extra layer.
Here’s my take on a fall-friendly shlep outfit that still maintains some personality despite prioritizing comfort and function. I can see myself wearing it anywhere from my son’s music class to the airport.
And finally, my outfit template for the chilly inclement weather that is eventually coming our way: a thin crewneck sweater tucked into jeans, coat, beanie, and — most importantly — a pair of chunky lug sole loafers from the brand Ash that I’ve had for years and always reach for if it’s gross outside but I still want to look intentional. I was tempted to do “more” with this outfit because it felt like it needed a pop of color somewhere, but nothing I added felt right. Maybe it’s perfect as-is, but either way, I’m excited to keep iterating.
Thanks for reading!
xo Harling
So my 3 year old JUST schmeared his berry popsicle across the chest of one of my fav cotton t shirts (le bonne shoppe) - you mom's boil trick absolutely works, holy crap. Wish I knew about this years ago!
I hate tucking in shirts, but find it next to impossible to get the proportions right! Looks like the key is finding a shirt which hits at high hip level? I'm referring to the look with the Chava shirt and Ayr pants.