Dear Avery,
I’ve been going out for casual drinks more often recently but every time, I always struggle with what to wear. What is appropriate happy hour attire?

Oh, happy hour. It’s the happiest of hours, really. There’s nothing I don’t love about casual drinks after work or class to take the edge off a tough day.

But such a casual atmosphere does call into question what the appropriate ensemble is. Too dressy and you look like a total amateur who thinks happy hour is synonymous with an evening on the Chip Strip. But too casual and you won’t fit in with all the real people with real jobs who have probably been looking forward to that stiff drink all day.

The trick is to find a happy medium. Choose one piece that’s a little dressy — a pair of heels, a nice top or even a dress — and then keep the rest of your outfit as low-key as possible. A casual bar or restaurant is not the place for your stripper heels and a bandage dress — and really, people, when is that ever O.K.? — but it’s also not the place for yoga pants. But this is not to say that your outfit should ever be middle-of-the-road or average in any sense of the word. You can still rock an awesome look, just keep it classy.

Option No. 1

I am a strong advocate of flannel and not just because I’m sort of a secret hipster (Editor’s note: It’s not really a secret). Flannel is comfortable, it is warm and most of all, it says “I’m casual and cool and I like beer.” Sure, you may look as though you share wardrobes with the guy on the Fisherman’s Friend package, but you look awesome doing it. And let’s face it: that dude would never look as good as you do in a pair of skin-tight, high-waisted black skinnies and chunky platform booties.

Flannel: ASOS, $70.16
Jeans: Urban Outfitters, $39
Booties: Zara, $49.99

Option No. 2

One of my favorite looks for winter is a warm cardigan paired with a loose shift dress and slouchy, knee-high boots. This look is not only versatile, but it’s comfortable without outwardly appearing that you’ve given up on life. Though you may be hesitant to wear a dress in the ever-unpredictable weather, you’ll be mostly warm if you wear a thick pair of tights — or sheers, if you’re feeling daring — along with over-the-knee socks. And don’t be afraid to pile on the layers elsewhere: a tissue tee under your dress, a chunky infinity scarf and a thigh-skimming wool coat will add warmth without all the bulk.

Dress: Forever 21, $17.80
Sweater: Nasty Gal, $58
Boots: Lord & Taylor, $69.99

Option No. 3

Believe it or not, colored jeans are still cool. I certainly didn’t think they’d stick around this long, but they’re here to stay and they just so happen to be the perfect thing for happy hour. They’re dressier than regular jeans but still more casual than, say, leather pants. When you wear them with a silky top that could transition from the office to drinks to even more drinks later on when you’re feeling frisky, you won’t have to worry about outfit changes. And although big black spots may say “Dalmatian” more than “sexy,” when paired with the most adorable pair of mouse flats on the planet, you’ll be on track to snag a veterinarian. Or, at the very least, a furry.

Top: Zara, $79.90
Jeans: Nordstrom, $60
Flats: Marc by Marc Jacobs, $198