Date night is fast approaching, and you have no idea what to wear. Sound familiar? It’s a dilemma that plagues us all; what to wear to impress and stand out.

Whether you’re meeting someone for the first time or going out on your 100th date, this guide will tell you exactly how to pick the right shoes for your date. 

1. Dress for the Occasion

Your shoes should be the last piece of clothing you put on, but you want to make sure you’ve incorporated them into your outfit before getting dressed. Most people don’t have endless shoe options, so it’s a good idea to plan your outfit around what shoes you can pair with it.

Make sure you know what kind of date it is, so that you can dress accordingly. You wouldn’t want to show up to an upscale restaurant in sneakers or sandals! On the flip side, you don’t want to be wearing heels or dress shoes for a picnic in the park. Unless the date is a surprise (lucky you!), then you’ll have ample time to plan ahead and pick the right shoes for the activity.

Make sure you know what kind of date it is, so that you can dress accordingly. You wouldn’t want to show up to an upscale restaurant in sneakers or sandals! On the flip side, you don’t want to be wearing heels or dress shoes for a picnic in the park. Unless the date is a surprise (lucky you!), then you’ll have ample time to plan ahead and pick the right shoes for the activity.

2. Be Comfortable

No matter what type of date it is, you want to be comfortable. Even if you look like a million bucks, your date will be able to tell you’re uncomfortable and not having a great time, and that’s not fair to them. A good rule of thumb is that if your shoes pinch or feel tight from the get-go, skip them.

They’re only going to get worse, so you’re better off in a pair of worn in shoes that won’t decimate your feet. You might be tempted to wear the sky-high stilettos if you’re only going to be at dinner, but unfortunately once you sit down your feet will swell slightly and the shoes will be twice as bad to walk in once you stand up. Luckily, there are tons of stylish but comfortable options for men and women that won’t give you blisters, like wedge heels for women or thick-soled dress shoes for men.

You might be tempted to wear the sky-high stilettos if you’re only going to be at dinner, but unfortunately once you sit down your feet will swell slightly and the shoes will be twice as bad to walk in once you stand up. Luckily, there are tons of stylish but comfortable options for men and women that won’t give you blisters, like wedge heels for women or thick-soled dress shoes for men.

3. Be Yourself

Your date wants to get to know the real you, so you’re better off showing them who you are. If your style is hip sneakers and jeans, then wear that. If you absolutely love the ritual of dressing up and looking chic, then by all means, dress to impress. Your date will get a glimpse into who you are and what you’re all about, and that’s a great way to start off any relationship. 

4. Matching is Outdated 

Your mother might have taught you to match your purse to your shoes (gals) or to never wear blue and brown together (guys), but that sage advice has become a little outdated. Nowadays, it’s frowned upon to match too closely; you want a look that is a little more stylish and free-spirited.

It can be fun to pair shoes with different outfit combinations, and see how it surprises and delights others. Stray a little from the beaten path and try out something new; you might just find a style that’s uniquely you.