Leather Jacketing 101

Turns out we're all leather jacket people.

Wearing a leather jacket does not come naturally to me. They’re loud (even when they’re not) by nature of them being leather jackets. They take up a lot of space. They are a decadent texture, even if they’re distressed, or vintage or not overly oversized. They can be tricky to dress around. By the time I have my shoes and bag and am walking out the door I find myself asking: “Is this too much leather?” But the leather jacket has become more ubiquitous than the trench! Options abound and I find myself craving this piece of outerwear that I have so easily avoided in the past. Therefore, today we are discussing five rules guidelines on how to navigate a leather-jacket-topped-outfit. Because there are TOO many good ones at our fingertips. And it’s what I want to wear. So you better believe I’m going to make it work.

It’s A Girl!

When I’m starting to feel too tough or bulky in leather, I lean on the most girlish things in my wardrobe: a pink skirt with ruffled hem. A scalloped, polka dot dress. A broderie anglaise collar. All elements that take an edge off.

Kallmeyer distressed leather jacket with a Datura raw silk, ruffle hemmed skirt, woven heels by The Row (not the same but how cute are these? I’d size down .5) Vintage croc top handle bag I found in Milan one kismet trip. Dorsey earrings. I feel great with all these super feminine pieces balancing out the bulkiness of the leather jacket look of the moment: stiff, big and boxy.

The Kallmeyer jacket (it is a size small, but probably could have taken XS) with an A’Court cotton shirt (similar here), Alex Mill chinos and Birkenstocks. I swapped out my typical chambray for a daintier shirt to soften the jacket and I am very pleased with the results.

Remember this scalloped, polka dot cutie from this newsletter? She is great company for a big leather jacket and sneakers. When I wear this, the dress flows behind me from under the jacket and makes me feel much cooler than I actually am. And isn’t that exactly what a great outfit is supposed to do!? Kallmeyer jacket, Margiela cardigan, CDG dress, Bode x Nike sneakers which are long gone but these are excellent.

Fresh Air

An essential element to wearing a leather jacket, and not having it wear you, is your SKIN! Too much leather can so easy swallow a person. So while I love the huge leather jackets that are trending, make sure you don’t get lost in there. This could mean pairing with a mini skirt for dinner. Or even just swapping your boot for a sandal (you might need to Uber come November) Or if boots are a must, try an unbuttoned polo sweater instead of a crewneck tee. Food for thought.

The Sei leather jacket (more sizes here and I’m wearing a size 2) with an Alaia mini skirt. Even with sheer tights, the skin to leather ratio works. With a Donni t-shirt, tights, Larroude wedges and old Row pouch. Maybe try her? More on non-leather accessories below.

Trying to make jeans and a leather jacket more exciting, I layered a vintage striped shell underneath instead of a simple t-shirt and opted for sandals to make sure I wasn’t totally covered from neck to toes. The Sei jacket, vintage shell (cute!), Auralee jeans, Attersee velvet bag, Manolo sandals.

Pairing this big, bulky Kallmeyer jacket with a sparkly midi skirt and Mary Janes (no tights!) to create a dressy/casual mix. I went for MJs instead of loafers because I wanted more foot to show!

Death by Handbag

Probably the most important thing I can do in this whole letter, is reinforce the need to pair a leather jacket with a non-leather bag. These outfits are cute and all, but if you throw a big leather tote over your shoulder, you’re just going to be uncomfortable. Am I wrong? It’s the true reason why this jacket is so hard, because you usually have to change your bag to make it all work. The things we do for a great outfit 🫠.

Kallmeyer jacket and jeans with the Row’s Idaho tote in canvas. This style is gone now. But there are so many great canvas totes out there.

The Sei jacket with Maria McManus drawstring pants and an old nylon tote from Elizabeth & James that I will be buried with.

Yes, yes this is another picture with a canvas tote. The point I am making here is that another great way to avoid looking too leather heavy is to wear your leather jacket with sneakers. BUT, consider swapping your jeans for slouchy black pants when you do so. It makes the whole thing a bit more thoughtful.

Big and BIGGER

If you ARE going to wear jeans, go for something a bit more dramatic. A basic jean can make the whole look just feel a little less like an outfit, if you know what I mean. Don’t be afraid of volume! Notice how I’m wearing a lower cut top in the first picture and letting my ankles peek out in the second. Don’t forget rule #2 above.

Proof that layering my biggest tunic and my biggest jeans under this big leather jacket are not a bad combo! Try to keep some skin visible. I fear with this concept you are going to have to just play around in your closet til you find the right mix. Kallmeyer jacket, Attersee tunic which is apparently already sold out! Humph! But we love the Rodebjer version too, scoop neck tank under that, Junya x Levis jeans (Look! Junya is doing their own $imilar version now!), Eastland mocs

Daytime-ifying this dressier leather with baggy grey jeans (I took a scissors to the bottom, they were SO long), Bode x Nike sneakers (Sockless, mind you. Friendly reminder that all anxiety-inducing sock stories are not worth your click!!!) and my trusty old Trademark bag. But let’s also talk about my black leather sneakers and suede bag. I think the leather on all fronts works here because firstly, it’s a sneaker so innately more casual. I am letting some skin show. And the suede is a light color and a different texture. This same outfit with black leather boots and a black leather crossbody bag would not feel as dynamic.

De-Prep Steps

This is not a new concept for us, heck I did a whole newsletter about it. But given that I naturally gravitate toward overt preppy pieces, leather has been a welcome addition to make it all resolutely less so. Pair your leather with moccasins and loafers. Ginghams and primary colors. Banker collars and cableknits. It seems to be an easy balance.

Is it giving you Rebel Without A Cause? But you know, the cute, Italian, skip in my step version? I’ve actually never even seen that movie. I guess I know what I’m doing tonight! Kallmeyer jacket. Saint Art sweater. Vintage skirt. Trademark bag but I guess the answer these days is a Picotin!? Emilia Wickstead x Grenson loafers

No I have not had time to take this Rohe blazer to the tailor yet but I like this idea of using a soft, more body con leather as a middle layer. It will be a fun way to dress up once it gets cold and you (I) don’t want to really bundle. The leather also helps the tan blazer, brown moccasins and full skirt feel a little less…mature. Rohe blazer. Sei jacket. Margiela skirt. Eastland mocs.

And of course, five unique options that are off the beaten trend report. From left: Bally (one left on sale here somehow!), Auralee, Dunst, Kallmeyer, The Sei

There you have it folks. Proof that all of us can be leather jacket people! If we just try on everything we own. You’ll get there.

Yours TRULY,

Becky