This is one of the many articles in the Mercury’s 2026 Halloween Issue. Find a print copy here, subscribe to get a copy mailed to you here, and if you’re feeling generous and want to keep these types of articles coming, support us here.—eds.
Portland goes hard on Halloween. In fact, All Hallows’ might be the one Eve of the year this city actually dresses up to go out. From December to September, our famously laconic metropolis is adorned with a mix of Columbia puffer vests and whatever counts as the “nice” Tevas. But the nightlife gets more adventurous in late October, thanks to a confluence of theme bars and a demographically significant population of former theater kids. When the sun goes down, the looks come out: alpha goths, Y2K scenester revivalists, art bike furries, and the rest of the Warriors-style crews that run these soggy autumnal streets.
How to dress impressively when the city is rocking half the drag wigs in circulation and ren faire-levels of sculpted leather? By using the terrain to your advantage. Dress for the bar, not the party, and you’ll control the battlefield. Here, then, are six “can’t miss” costumes to pair with Portland’s hottest Halloween haunts.
“Charley Crockett Contemplating the Vanishing West” Costume
The cowboy is a complicated and often compromised figure, indelibly tied to the exploitation and cruelty of frontier life. But the Old West also exists in America’s collective memory as a time of fierce independence and stark moral choices, where good was tested against evil without the mediating forces of civilization. Observe the twilight of our national creation myth, and if anyone suggests getting with the times, give them your best rueful Sam Elliott sigh.
Destination: The Last Rodeo (6637 SE Milwaukie), true to the name, feels like the kind of place a washed-up bullrider might grab a shot of straight bourbon to settle an unsteady grip. Or sidle over to Rhinestone (2100 SE Clinton), a glammed up Southwestern watering hole with more of a “washed-up rodeo clown” vibe.
“Video Store Employee Poised to Ruin Movie Night With Terrible Recommendations” Costume
Long ago, when the Earth was young, the fate of movie night depended on the sage wisdom of whichever teenage stoner was working the counter of the neighborhood video store. Usually they’d be good for a deep cut kung fu flick or some underseen British romcom. But on moonless nights when the hash was dank, they’d punish their constituency with confident endorsements of the most rancid trash in inventory.
Destination: Help misguide impressionable peers with imperious pronouncements at Cult Classics (1308 SE Morrison), a video store-themed bar from the golden age of physical media, bathed in the warm glow of old-school tube TVs. Or get hyperspecific at Bar Hollywood (4128 NE Sandy), an intimate lounge devoted to the collected works of David Lynch.
“Swinger at a ’70s Key Party, but There Are No Keys Left” Costume
The ’70s may not have been a subtle decade, but people sure did seem to connect back then. The key party, for example, was how polycurious cul-de-sac culture combatted decision fatigue by assigning sexual partners via a big bowl of everyone’s housekeys. This look captures the thrilling contradictions of the age: the V-neck leisure suit displays confidence, while the look of growing concern suggests “this was a bad idea to do with an odd number of people.”
Destination: We’re in the midst of a midcentury bar revival, so there are a lot of options for this one. But none quite so on point as Keys Lounge (533 NE Killingsworth), a quintessential Nixon-era jazz bar in a former locksmith’s shop. LaVerne’s (700 NE Dekum) is another strong contender, with the exact right ratio of wood laminate to squeaky booth vinyl.
“Off-Duty Sexy Librarian” Costume
The “sexy” prefix can be attached to any costume, but the sexy librarian is a classic for a reason. Straining tweed jackets, precisely perched hornrims, pursed lips poised for a good shushing… it’s all there, crackling with erotic potential. But even objectified archivists deserve some time off. Loosen that stiff collar, crack a cold one, and tell us how you really feel about the Dewey Decimal System.
Destination: Nothing implies “I love organizing by type” and “I drink” like a trip to the Multnomah Whiskey Library (1124 SW Alder), which combines the elegance of a Gilded Age philanthropist with the liquor reserves of a Gilded Age robber baron. For a more whimsical approach, there’s the Novel Book Bar (322 NW Everett), which leans more towards a modernist Bohemian playpen with a bunch of quirky book nooks.
“Soft-Boiled Private Eye” Costume
All that’s needed for a decent PI ’fit is a thrift store fedora and a healthy distrust of institutions. But this is 2026, so maybe integrate some therapy breakthroughs into the weary internal monologue. And a little moisturizer before bed couldn’t hurt, especially on late nights investigating the injustices of a corrupt system.
Destination: What makes a classic noir bar is the lighting, or rather the lack of it. Imagine a lonely tungsten bulb holding out against the encroaching darkness, and also there’s tequila shots. Side Eye (612 NW 21st) features the most cinematic lighting in town—no coincidence with Cinema 21 next door.
“I Dunno… Like a Witch or Something?” Costume
There’s a reason the iconic pointy hat makes an appearance at every Halloween party. As Dianne Wiest said in Practical Magic, “there’s a little witch in all of us,” and also, everyone looks good in black. But there are plenty of variants that say “fire burn and caldron bubble,” too… consider the goth witch, who trades black muslin for PVC, or the yoga witch, who knows which inversion pose goes best with the current phase of the moon.
Destination: Portland maintains a thin veil between the mystical and mundane, which means there are a good number of watering holes with an aesthetic that is both vaguely witchy and Insta friendly. Bar Loon (3326 SE Belmont) is one such establishment, beguilingly kitted out in dripping wax and smoldering incense. Or consider Fates Bread and Bottle (6664 SE Milwaukie), a Sellwood-Moreland-area wine bar that’s well equipped for a bit of scrying alongside a full-bodied malbec.