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The 11 Classic Fall Outfits Em Is Going To Wear ALL Of the Time (Plus An Incredible Dupe)

We had such a busy and buzzy week over here, with three reveals in three weeks (coming soon), but one has to wear clothes, and it’s fall, so without further ado, here are some of my current favorite classic fall outfits that I wore a lot to work this week.

Trench Coat | Purse | Jeans | Shoes

I feel like a non-bulky trench coat is hard to come by. But this one doesn’t have all the bulk of a trench, but it still has the shoulder straps, cuff detail, and trench look. It cinches at the waist so you can control the shape. Shout out to this super affordable bag that looks expensive (and is big enough for a laptop).

Trench Coat | Boots

I ordered this one from Quince, and it came after our shoot, but goodness, it’s good. It’s structured but still drapes nicely. It comes in a few different colors and is just perfectly classic, again, not being too bulky (if you can’t tell, I keep trying on trench coats and they are all just unflattering and add so much volume in places where you don’t want volume). This one just falls really well. It’s true to size. I’m wearing a small and can have a thin sweater but not a thick one. So if you are in between sizes and want to layer over anything thick, then size up. Also, THOSE BOOTS. Merlot + kitten heel + Italian leather = so so soo good (I wear them with jeans, too).

Sweater | Purse | Jeans | Belt | Shoes | Gold Charm Necklace

This sweater is such a fall hit. I ordered it in two sizes (S and XS) and am wearing an XS, so consider sizing down. It’s a thicker knit but not too bulky. Great dropped shoulders and roll neck, not to mention the perfect fall color palette. The jeans are awesome – from Target, their “boyfriend” jean. They are a great wash and length, low- to medium-rise, and $40!!! I’m wearing a size 2, so size down. The penny loafer mules are so comfortable and still slimming (I’ve tried on a lot of penny loafers, and they can be so bulky, stiff, heavy, and uncomfortable). These are soft and so comfortable.

Sweater | Skirt | Socks | Shoes

We aren’t done with the schoolgirl look apparently, but I’m really into it (those socks are key, FYI). The sweater is a fantastic color palette and fit, roomy (so size down; I’m wearing an XS), and the faux leather skirt is oddly classic and seasonless. Like, I think I’ll wear it a lot, year-round. Shoes are so pretty but need some breaking in.

Sweater | Jeans | Belt

J.Crew does sweaters so well. This quarter-zip is so soft, with a subtle classic cable knit and very layerable. It’s roomy and cozy and high quality enough for work, but you bet I’m wearing it on work-from-home days. The jeans are a fantastic barrel, especially if you like mid-high rise. They are true to size (I’m wearing a 27) and have great front pockets (which are flattering).

Jacket | Jeans | Boots | Burgundy Beaded Necklace

For those of us who might want a shorter “trench,” this one has a great high collar and cuffs, but cinches at the waist. It comes in chocolate brown, which was so pretty (but they didn’t have it in my size). Wearing an XS, but the small fit too, just more voluminous. Quince Bella jeans in off-black, for the win again, and of course their kitten-heel tall burgundy boots that are a fantastic fall addition that feels both on trend and timeless.

Hat | Jacket | Shirt | Shorts (same cut) | Socks | Shoes | Multi Colored Beaded Necklace | Gold Charm Necklace

The number of times I look in the mirror and think I look like a Boy Scout is more than would be predicted at this age. And yet this is such a normal weekend look for me. The oversized denim jacket is $60 with great big pockets, slimmer arms, and a corduroy collar. FANTASTIC. I’m wearing an XS, and it fits, but if you want to layer it over a sweatshirt, order your normal size. I LOVE these new caramel brown Sorels. They are both cool and extremely comfortable while being more neutral than my blue Seavees (which I also wear a ton).

Jacket | Shirt | Shorts | Socks | Scarf (unavailable) | Shoes

Madewell is playing hard with this fantastic cargo jacket. Another totally timeless fall staple that is so easy to throw on and looks on-trend without being too trendy. Parker shorts, FTW, and my new mules, which I think look particularly great with socks.

Sweater | T-Shirt | Jeans | Shoes | Burgundy Beaded Necklace | Gold Charm Necklace

I won’t stop praising or wearing this cardigan. It’s a four-season staple for me that can be thrown over so easily because the knit is this magical weave that is easy to layer over, clings to nothing, and I even wear it without a shirt underneath it with a silk skirt, which is my version of cocktail attire. I have it in cream, too, but I wear the navy almost like a jacket many days. And yes, those sneakers are awesome – comfortable, cool, and neutral (look good with anything). The jeans are new and good, mid-rise with a cut hem (true to size).

Blazer | T-Shirt | Jeans | Belt | Shoes | Burgundy Beaded Necklace | Gold Charm Necklace | Bag

I LOVE the Madewell blazer that I wore last week, but it was $250. So I ordered this to see if it could compare (at $100). I still like the warm tones of the Madewell one for fall, but this one is fantastic. I will likely wear it more like a jacket, less as part of business attire. It is oversized in a way that is good – like menswear. The shoulders are structured, and then it falls (so it’s not trying to be all body-con). I’m wearing a small, and it layers easily over a thin layer. It’s fantastic, and I hope they come out with new colorways (like a warmer tweed or a navy).

Sweater | Pants | Belt | Shoes | Multi Colored Beaded Necklace | Gold Charm Necklace

Hold on to your dupe-hating; Target has nailed the viral Free People slacks (which were probably knocked off of some higher-end brand, BTW), and my goodness, they are fantastic. They have the same slight barrel shape, curvy fit (roomier in the hips, come in at the waist), and the back has the roomy pocket detail. I will say that the Free People ones are more “barrel-y” and have a more pronounced horseshoe shape. I like them both a lot but was so impressed with the Target versions considering how affordable they are ($35 – wearing a size 2). The cardigan by Quince, which is thick enough to not need a shirt underneath, but thin enough to just be a shirt. The shoes are from Anthropologie, and I love the shape but returned them because I felt that the leather on top is too thin and could wear out too easily.

The big hits for me are the Target jacket and pants, the mules, that Madewell sweater, and my continued love for Quince for quality staples.

Ok, see you tomorrow! xx

*Photos by Kaitlin Green

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