My Realistic Fall 2024 Outfit 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.

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Still Here overalls, Filson jacket, Eliou cap, vintage loafers, Warby Parker sunglasses

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.

Vintage trench (similar here), vintage dress, The Row boots (found here secondhand in a size 10), vintage necklace

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.

Chava button-down, AYR pants, Little Lifner bag, Nike sneakers

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.

Babaa sweater, Dries van Noten pants, vintage necklace, Margaux loafers

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.

Tory Burch pants and shirt (you can often find on Poshmark using the keyword phrase “Tory Burch iced lemon”), Guest in Residence sweater, Le Orsine slippers, Brinker & Eliza pendant (I took the pendant off the original chain and strung it onto a cord).

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!

Merlette skirt, J.Crew sweater, The Row boots, Arielle Ratner pendant, vintage fish pendant

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.

Preloved Edit sweater, Tory Sport pants (found here secondhand in a size small, and here and here in an extra-small), vintage loafers, Little Liffner bag

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.

Autumn Adeigbo pants, vintage blazer, Old Celine top (via The RealReal), DIY necklace, Chanel slingbacks

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.

Nikki Chasin cardigan, AYR pants (you can find them on Poshmark using the keyword phrase “AYR metropolitan pants white”), Brandy Melville long sleeve T-shirt

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.

Vintage trench, Still Here skirt and belt, Gap T-shirt, The Row boots, Warby Parker sunglasses

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.

Maria McManus dress, High Sport pants via The RealReal, Yunni Buffa flats

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.

Vintage trench, vintage button-down, AYR pants, J.Crew sandals, Eliou cap

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.

Sezane coat, Chava button-down, Dries van Noten pants, Margaux flats, J.Crew sunglasses

Basically a remix of my pajama-adjacent outfit template above, with an extra layer.

Sezane pants, Guest in Residence sweater, Still Here jacket, vintage fish pendant, Beck choker, Ralph Lauren bag, Eliou bag charm (I also love this $34 one on Etsy), Mansur Gavriel loafers (similar here).

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.

Sezane coat, AYR jeans, J.Crew sweater, Buck Mason beanie, Ash loafers, Arielle Ratner pendant, vintage fish pendant

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