Ask a Betch, Dating Edition: WTF Do I Wear To A Winery Date?

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Bonjour, Betch! It’s me, your dating fairy godmother, here to tell you all about your life. No, actually…I’m not. (Sometimes feels like I can’t even get my own in order tbqh.) But what I am here to is tell you how to dress for those dates that seem designed to have us standing in front of our closets crying about how we have nothing to wear.

How am I qualified? I was single for most of my 20s and in 2015 went on something like 150 first dates. That isn’t an exaggeration. Any questions?

I’ll be answering your Q’s as they roll in. So if you have any questions about what to wear on a date (or, truly, what the best of anything is) make sure to drop us a line.

Q: Help, Betch! What do I wear to an Oktoberfest celebration at a winery if I’m not a brim-hat-and-cowboy-boot girlie?

A: Oooooh look at you getting all autumnal! I love this date idea, and totally hear you on not wanting to wear a brim hat. TBH, I feel like those suckers are a lot more high maintenance than they deserve to be. I mean, do you expect me to keep that thing on my head after a few glasses of sauv? Neaup!!

In this case, I’d advise something that’s going to keep you warm, but that’s also cute and cozy. My prescription for the Oktoberfest date is this: A pair of straight-legged jeans (skinny’s cooler cousin), an oversized flannel (bonus points if you can steal one of his), knee-high boots, and a cute lil beanie. Now I know what you’re thinking—those boots look a lot like cowboy boots. But they’re cute, they’re elevated, and I promise you when I say you’re going to get a ton of wear out them. Plus, they look so cute with these straight-leg jeans. Just tuck them into the boots and allow them to bunch a little, à la Princess Diana. Just trust me, betch. You’re going to look sick.

Shop the look below!! Until next time!

Reformation Cynthia High Rise Straight Jeans

Beaully Women's Flannel Plaid Shacket

Dolce Vita Blanch Boots

Rag & Bone Addison Wool Beanie


Maria Del Russo
Maria Del Russo
Maria Del Russo is the Branded & Affiliate Content Director for Betches. When she isn't at the office, you can usually find her in the kitchen, yelling "That tastes SO freakin' good!" at nobody in particular.