I have a complex about black leather jackets. I love them — that’s not the complex — because of their weight and their texture and their layering abilities and the way they make you feel instantly “cool” — but I can’t stand the fact that every time I wear one out to a bar, I feel like I’m wearing the same exact outfit as every other person in the leather jacketed room. That’s probably because there’s something about a leather jacket that makes you want to style around it: black jeans, black shoes. Black or white T-shirt underneath. I totally get it. It’s easy! It’s perfect for fall and winter, it’s a classic, it looks great.

But again, me and my complex. I have the opposite of Haley’s twin thing. Even though I probably am dressed like more people at any given time than I realize (I’m not exactly pushing boundaries over here in my jeans and sweatshirt), letting myself lean into that leather jacket uniform almost always results in outfit frustration.

It’s not just leather jackets, however. There are more quintessential fall items that trick me into styling myself like everyone else in the coffee line, like the “it’s officially sweater weather!” sweater (which, to me, typically means cream, ribbed or cable, with a turtleneck or some element of “chunk” to it), or a pair of leather ankle boots.

So I decided to create a slightly less predictable outfit around each of these items to prove (to myself, really) that they don’t have to be styled so literally.

The Leather Jacket

Part of me thinks that when you boil it down to its essence, the leather jacket can be worn with anything if you let it. But that makes it more complicated! Because part of the leather jacket’s appeal is that when you know you’re planning on wearing it — particularly if you’re going “out” — the outfit is planned for you already. (Again: that black jeans, white T, black boots or heels look.) So the main key here is to set up an alternative template for your leather jacket, one that feels just as automatic but looks different in comparison to your leather-jacketed bar patrons. And look! I made one for you:

Wear a patterned cardigan over a turtleneck with a pair of camo pants. Add shoes that clash, jewelry — maybe pin a set of earrings to the close-topped, open-bottomed cardigan like you see here — and go get your leather jacket. Tell it you love it and you’re sorry you ever doubted it.

The Cozy Sweater

All you have to do to get your cozy sweater out of routines-ville is repeat after me: I do not have to wear my sweater with jeans. I mean, I can if I damn well please, but I do not have to.

Why is that so easy for me to forget?

No matter, because this outfit’s just as easy to put on: Cozy sweater, below knee-length-ish dress, plus boots that hit right at the dress’s hem. That is it. As for what we did here specifically: layered a turtleneck sweater (this one is by Naadam and it is so soft that I was very jealous of the lovely Meisha’s neck) over a tented tunic then added a slip underneath for a layer of protection against the fall breeze — plus, I liked the way it looked. As for those black and white boots, well, I could talk about my love for them until the cows come home.

The Chelsea Boot

Chelsea boots are almost always my gut instinct shoes to pair with the above mentioned knee-jerk outfit of jeans and a sweater. With a leather jacket over it. But now that my leather jacket’s about to be busy all the time with camo pants, and my sweaters all want to hang out with dresses, I have to find a worthy set of friends for that which keeps my feet autumnally happy. Enter the ultimate errand outfit: a striped cotton turtleneck, a windbreaker and a pair of sweatpants. (They usually hang out with my sneakers, but my sneakers just took off running…) Errand outfit, meet Chelsea boots. Chelsea boots, meet errand outfit. I think you two will be supremely happy together. You certainly look like a charming couple!

Photos by Edith Young. Modeled by Meisha Brooks at Muse. 

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