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5 Ways To Wear Your Favorite Jeans For 5 Different Dates

first date outfit

If the first thing that runs through your head when you get asked out is ‘what am I going to wear?!?’ then girl, you are not alone.

Making a first impression is always daunting and it’s especially tough when there are a million other question marks floating around in your head (like ‘will it be awkward?’ and ‘should I offer to pay?’)

When it comes to dressing for a first date, I believe this is the cardinal rule: Make sure you’ll feel comfortable in what you’re wearing. I wore five-inch heels on my first date with my boyfriend because I happen to feel more graceful and confident in stilettos – but if you’ll be stumbling around in them all night, go with flats. Don’t show more skin than you’re comfortable exposing. Don’t wear a trend if you aren’t sure if you can it pull off or a shirt that may or may not become sheer in certain lighting. The bottom line is, don’t add another thing to stress about into the mix. Beyond that, I think it’s best to wear something memorable yet neutral, something that’ll be approrpiate for a few different scenarios.

Because it’s the middle of winter, you also probably want to stay warm. In light of that, we’re showing you five separate ways to style your favorite pair of jeans – and item you’ll almost certainly feel comfortable in – for five different settings.

Scenario 1: A day date

Daytime = casual. Wearing jeans is a no-brainer for this sort of date. The question is, how do you style the rest of it? I love the option of wearing an oversize boyfriend-style flannel shirt. It’s not only a really cute look, it’s also super comfortable (both literally and figuratively.) Add a cute, distinctive touch by topping off your outfit with a cute fedora. Finish off the look with some great brown riding boots – they’re super easy to walk in, which is great since you may end up being on your feet for a while.

 

Scenario 2: A movie

Since movie theaters tend to be freezing, layering is key here. Watching a movie is all about being cozy and topping your jeans off with a nice chunky sweater makes this easier than ever. A cardigan works especially well here, especially when paired it with a soft tee. Since the oversized fit of a slouchy cardigan can start to look dumpy, counteracting this with a stacked-heel boot (if you’re okay with that) is a great idea. Finish it off with simple makeup and a nice big handbag.

 

Scenario 3: Drinks at a casual bar

If you’re going for drinks at your local dive bar, keeping it casual is a great idea….but throwing a subtle element that dresses your look up is also a great idea. Pair your jeans with a simple striped top and layer a fun statement necklace over that for a bit of glamour that won’t look out of place in a laid-back setting. Finish the look off with some fashion sneakers, maybe Converse or a cute pair of slip-ons. These rules apply to any kind of sporting event.

 

Scenario 4: A concert

If your first date is taking place at a music venue, it’s time to let your edgy side come through. If you own any band tees, this is the perfect time to break one out (bonus points if you actually like the band!) A leather jacket is the perfect compliment to this look, whether it real or faux. As for footwear, flat moto boots bring the edge and are foot-friendly if you need to stand the entire night. Since this look is super cool and not overly girly, this is the perfect time for some bold lipstick.

 

Scenario 5: A fancy dinner

If your date is taking you to a nice restaurant, you probably want to get a bit more dressed up. You can still totally do this while wearing jeans as long as the restaurant isn’t over-the-top fancy.) Stick to dark wash or black denim and pair your jeans with a a pretty silk blouse or a nice tank top with a blazer. Add some heels – pumps are a great option if it’s warm enough (if you’re going with jeans there’s a good chance you’ll need to dress it up somehow. Play up your first date glow by applying a bit of highlighter to your face. It looks beautiful in candlelight!

 

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  • Zara HCOLLEGECANDY Writer
    I'm a Chicago-based writer and graduate of the Medill School of Journalism who has written for sites like Cosmopolitan.com, Seventeen.com, MarieClaire.com, Glamour.com, Parents.com, Racked, Thrillist and The Huffington Post.