Couple taking a walk in a park at autumn, What to wear on a first date

4 Fall First Date Ideas and What to Wear to Each One

We know first dates can be nerve-wracking, and figuring out what to wear is half the battle. You want to look polished, but not too polished, cool but not too cool—basically you want to nail the, "I look ridiculously good, without trying too hard" vibe. To get you started, we put together some fun date ideas, plus four fall looks perfect for meeting someone new. 

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Date Idea #1: Visit a pumpkin patch or apple orchard. You’ll tap into the cozy fall feeling with a hayride or corn maze, all while taking in the fall colors and sipping hot apple cider. 

What to Wear: Show off your outdoorsy side with practical (but fashion-forward!) hiking booties and overalls. Layer up with an oversized sweater to add an extra dose of warmth and style.


Date Idea #2: Spend the afternoon playing tourist in your own city. Stroll around parks, check out museums, pop into cool one-off boutiques, and see anything else your town has to offer that you might not explore on a typical day.

What to Wear: For a date filled with walking, sneakers are your best bet. Dress them up with funky trousers and a fitted turtleneck to streamline the look.


Date Idea #3: Grab a latte at a local coffee shop. We all know first dates don’t always go as planned, so if you want a quick escape, keep it simple and meet for coffee.

What to Wear: Sport jeans and a sweater to look casual but put-together. Finish the ensemble with fun white booties for a playful touch.


Date Idea #4: See a comedy show or catch some live music. It’s always helpful to have built-in entertainment to kickstart conversation and give you something to bond over.

What to Wear: Get ready for an evening out with a patterned midi dress and a leather jacket. If you think you’ll be overdressed for the venue, tone it down by layering the dress over a tee for a look that’s relaxed and on-trend.

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