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What to Wear on a First Date

Posted by Roam Often on
What to Wear on a First Date

What to Wear on a First Date

Got a first date coming up? Lucky you. That’s exciting! Now you just have to figure out what to wear.

Don’t worry. Dressing for a first date doesn’t have to be tricky. Follow these tips to make it easy, make it fun, and enjoy your first date!

What to Wear on Your First Date? Rule Numero Uno

Before we get into the outfit ideas, remember the golden formula of what to wear for first dates: 

Comfortable + Confident = Sexy

The most important thing is to wear whatever allows you to be you and be the awesome person you are. Your date outfit should be something that makes you feel confident, so you can calm those butterflies and be present for your date. 

When you’re comfortable, you can showcase your best self and let the person know who you are—and you’ll be more able to focus on who they are, too! It’s a win-win.

As comfy as sweatpants are, though, they probably don’t make you feel super cute. So let’s get into some ideas for what to wear that strikes that perfect balance of comfy yet chic.

Man hugging a stylish woman on a first date

What to Wear on a Casual First Date

When meeting for a casual first date, it’s best to dress for any occasion. You don’t know if your coffee meet-up turns into dinner and drinks, or your dinner date ends with a flirty game of skeeball at an arcade. That’s part of the magic of a first date! 

Fingers crossed, you find the one. So you want an outfit that transitions well from one venue to another.

On that note, some fitted pants or jeans, paired with a cute top, make it much easier to go with the flow. That top might be a sweater, tank, or off-the-shoulder number. 

If you’re more of a dress and skirt girl, you might opt for a romper instead, in case you do something with a bit more movement. You can always save your dress for the second date!

Comfortable shoes will also help you stay effortlessly flexible and relaxed. We love a pair of sandals, wedges, booties, or even fashion sneakers. If you’ve got a go-to pair of power pumps, feel free to wear those—just make sure you can walk in them.

As for patterns or solids, we say solids, and lean into the stylish power of whites and blacks. These are easy to pair, easy to dress up, and easy to dress-down as the day progresses. You can’t go wrong. 

For more style inspiration, check out our Pinterest board of What to Wear on a Casual First Date.

What to Wear on a Dressy Dinner Date

Here’s a little secret: figuring out to wear for a dressy date is actually way more straightforward than a casual day or night date.

You already know it’s going to be a dressy dinner date, so dress to impress! This is the time to bust out your LBD (there’s a reason they’re perennially popular), or wear your favorite dress or skirt. 

Then, add some heels to dress it up. Here’s where you can get creative and reveal a little personality. Go for a classic pair of nude or black pumps that keep the attention on your stunning dress. Or, wear some thigh-high boots to stay cozy and edgy. Stilettos are great if you want to show off those gams.

Solid colors are still a smart choice for dinner dates. You don’t want your outfit to distract your date from where the attention should be—on you. It’s all about that eye contact, baby! 

Use jewelry to accent your favorite features. A long necklace can complement your cleavage, earrings can bring attention to your decolletage or face, and a bracelet can highlight those beautifully manicured hands. 

Speaking of jewelry, if you’re going from one venue to another, or straight from work to your date, don’t forget to bring along a travel jewelry case. With The Wanderer, you can instantly change up your outfit with a quick jewelry change. Plus, it’s small enough to fit in your purse!

For more style inspiration, check out our Pinterest board of What to Wear on a Dressy First Date.

Roam often, stay stylish.

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