Plus-Size First Date Outfits

A List of Imagined First Dates, and the Outfits We’d Wear to Them

No one has ever claimed first dates to be easy. Not even in those cheesy romantic comedies we all secretly adore—where so much of love is portrayed as some sort of fairy tale—are first dates a seamless, perfect experience. Meeting someone for the first time and hoping to feel a connection that will launch us into a whirlwind romance typically isn’t as simple as sitting down to dinner—or at least it doesn’t feel like it. When it comes to going on a date with someone for the first time, we factor in so many things: the location, the activity, the weather and, of course, the outfit. Deciding what to wear on a first date might actually be the hardest part of preparing for a one, which is why we’ve decided to break it all down and create some plus-size outfit ideas catered to all types of first dates. If the dating process can’t be easy, as least figuring out our outfits can be.

While just about any activity can be turned into a date—from a simple walk on the beach to trying out a new karaoke bar—there are definitely some classic first date scenarios we’ve all seen (or been on) before. Consider these first dates categories from which you can have plenty of offshoots. For instance, going out to dinner is a tried-and-true date activity—but this type of date doesn’t look the same each time. Perhaps the restaurant is a formal place right by the water. Or maybe it’s a ridiculously hip new eatery that has a month-long waiting list. It could also be a cute diner close to where you live. It’s all still dinner, though, and you can use the same outfit recipe no matter the specifics.

Below, we’ve taken seven different classic date scenarios and created plus-size outfit recipes for each—so you can focus on getting to know someone new rather than worrying about your ensemble. After perusing (and shopping) these looks, you might even realize that figuring out what to wear on a first date can be an enjoyable process. Just remember that how you dress is expression of you, and that if you feel confident in what you’re wearing, it’ll shine through. So take a deep breath and have some fun with it, K?

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1. The Romantic Picnic Look

Whether you’re headed to the park for a spread worthy of your Instagram feed or sitting at a picnic table with take-out from a local restaurant, throwing on an easy and breezy mini dress with oversized sunnies and colorful sandals is a low-key way to stay both cute and comfortable.

A collage with a black and white mini dress, pink sandals, and black sunglasses.

shop the look

dress — $24.99 from H&M
sandals — $58 from Anthropologie
sunglasses — $59 from Revolve

2. The Traipsing Around a Museum ‘Fit

When you’re walking around a museum, art gallery or the like, you want a look that’s casual but also pulled together. You want your ensemble to say, “Sure, that painting is nice, but her early work is truly inspiring. Let’s discuss.” So put on a pair of paperbag waist pants, a cool graphic tee and some loafers that are comfortable enough to walk in. Boom—You’ve got it made.

A collage with brown trousers, a graphic tee, and white mule shoes.

shop the look

top — $58 from Anthropologie
pants — $29.99 from Target
shoes — $64 from Topshop

3. The Beach Babe Ensemble

For a walk along the beach, a full-blown day by the water or even a pool party date, you can’t go wrong with a fun one-piece swimsuit that acts as a top. Pair it with some cute matching shorts, then finish off the look with some fun sunglasses. You’ll be ready to hit the water if it goes that way, but look chic enough to never get your toes wet, too.

A collage with a green tie-dye swimsuit, teal shorts, and star-shaped sunglasses.

shop the look

swimsuit — $17 from Missguided
shorts — $19.80 from Torrid
sunglasses — $75 from Crap Eyewear

4. The Hot New Restaurant Get-Up

Figuring out how to dress for a dinner date might actually be the most difficult outfit situation, due to the fact that the category is so broad. That being said, though, it’s always a safe bet to toss on a statement mini dress and pair it with some simple accessories—like black heels and a pretty purse.

A collage with a black and black mini dress, silver purse, and black heels.

shop the look

dress — $228 from Anthropologie
shoes — $68 from Topshop
purse — $44 from Topshop

5. The Casual Coffee ‘Fit

For a casual coffee shop or ice cream date, play it cool with some light wash jeans, a sweater (You can keep it lightweight if it’s the summer!) and fashion sneakers. You’ll match the cozy aesthetic of the location, but still look absolutely adorable.

A collage with light wash jeans, a red sweater, and gold and gray sneakers.

shop the look

sweater — $148 from Anthropologie
jeans — $59.85 from Torrid
sneakers — $110 from Gola

6. The Classic Movie Date Ensemble

These days, there are so many different movie-watching experiences, but the outfit recipe remains the same. Whether you’re at a classic movie theater, a vintage-inspired drive-in or a rooftop movie set-up, wearing some dark gray jeans, a loose-knit sweater and cute sandals (easy to slip off—just in case) is a no-brainer.

A collage with a cream sweater, gray jeans, and yellow sandals.

shop the look

sweater — $69.50 from Madewell
jeans — $59.95 from H&M
sandals — $100 from Anthropologie

7. The Easy (but Cute AF) Concert Look

A collage with a denim jumpsuit, animal print sneakers, and a printed phone case.

shop the look

jumpsuit — $34.99 from H&M
sneakers — $90 from Anthropologie
phone case — $45 from Casetify