Newsboy Caps, Tweed Suits and Other Fall Personas to Try On

I have the best idea ever for you and your friends this fall, or autumn if you’re fancy: Find a nearby photographer (professional and willing or amateur and bored), identify his/her favorite bribe, then dangle said metaphorical carrot in front of your potential camera person’s eyes and lure all — friends included, obviously — into a wonderfully dramatic photoshoot.

If summer was the season of the plandid, let fall be the season of the full-blown editorial.

For one thing, why should engaged couples have all the fun? Your ass, whether single, dating or betrothed, deserves a bale of hay to pose upon in all your solo glory just as much as a pair of lovebirds. You have clothes to show off, angles to attempt, fashion fantasies to be enacted. Late September’s golden sun shines for you just as brightly as a diamond ring, you know. Let it dapple your face as you contort your body in the pants that made you pray for an end-of-summer cool-down.

Stella von Senger, Berlin-based makeup artist who showed us how to wear fanny packs and rethink the suit, did just that. She embraced the East Coast equestrian theme that autumn has a tendency to bring out in everyone, but styled it with extra quirk, extra irony, risky hats…and a pug.

Scroll down to get inspired for your own photoshoot ideas. As you take note of the shot already in your head, mentally prepare for your fall persona with nine foliage-friendly outfits. And please! I beg you: Upload any editorials you and your friends happen to take of one another into the comments section.

Ready, set, pencils out! Think about…

Ask Yourself: What’s Black and White and Red All Over?

Existential trick question. The answer: You are. You already know that there are no rules around white pants. Try your autumnal ivory slacks with black, and if you don’t have red hair to accent the human checkerboard you’ve created, find a red wall. Oil painting portrait and pug are highly encouraged, but optional.

Think About the Side Saddle Suit

I can hardly look at this outfit without my heart breaking. I once had a jacket like this, and then I lost it in drunken debauchery. I’ve mourned it ever since; the hunt for the perfect replacement won’t end until I find it. But enough about me, this is about you: Find a plaid jacket with a skirt to match it. A black tee underneath will do, and I will never say no to a ribbon-wrapped straw hat.

Find a Top-Notch Trophy Jacket

Still seeing red, toreador: Now’s the the time to invest in something ketchup-colored and houndstooth-checked. Also, don’t let anyone ever tell you that a wide straw brim is exclusively for the beach. Bonus photo points if you find a man in tartan suspenders who will loan you his horse.

Consider, Yet Again, Carrie Bradshaw’s Early Aesthetic

It is unavoidable: The newsboy cap is back. Pair yours with a ruffled shirt. The year 2000 called, it said, “Find a velvet Prada purse at a vintage store while you’re at it.”

Raid Your Grandfather’s Closet

And his bar, while you’re at it. A white supper jacket goes great with printed pants and boat shoes so long as you find a gingham waistcoat for the full package.

Piece Together the Last Bits of Summer

Just because it’s fall doesn’t mean your summer clothes are completely done. I bet you have a few puffy sleeve shirts still lingering about you never fully wore. Hook, line and sink yourself some picnic table pants, clash together and have at it.

Important: Field Coats Are Practical But Need Drama Added

I love a field coat, but you’ll feel like you’re grocery shopping in Greenwich without a little weird pizazz. A massive scarf tied around your head, as Stella has done, will do the trick. Wear a sweatshirt underneath. Don’t forget same-flesh-tone-as-your-face-colored glasses.

Let Driving Moccasins Be Your Loafer Alternative

Vintage Tod's shoes, Henriette von Grünberg dress, vintage Hérmes corset, Stella's mom's earringsVintage Tod's shoes, Henriette von Grünberg dress, vintage Hérmes corset, Stella's mom's earrings

They pair well with everything, magically, but go especially well with an all-red, caped ensemble. Wear this to do your morning neighborhood greeting.

Finally, Find a Three Piece Suit and Ditch the Pants

Fiona Bennett hat, Pallas Paris jacket, Aeron skirt, all else Stella's husband'sFiona Bennett hat, Pallas Paris jacket, Aeron skirt, all else Stella's husband's

You’ll want the blazer and the waistcoat, but go for different trousers. Add a tie, but keep it monochromatic with the shirt. And good lord, another newsboy cap? Yes. I suppose so. But do what you want — so long as you do it for the photo. After all, we’re preparing you for your autumnal editorial.

Words by Amelia Diamond
Photography: Denise Bodden, follow her on Instagram @denise.bodden.
Styling, art direction and modeling: Stella von Senger, follow her on Instagram @stella_vonsenger.

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