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No More Socks and Sandals: How to Knock Your First Date Outfit Out of the Park

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There are very few things that can be as nerve-racking as first dates, especially when you’re meeting someone you’ve only interacted with online. You want to make an excellent first impression appearance wise, while at the same time showing off your personality – or, at least, that should be the goal.

Here’s a fun fact: when you look and feel your best, other people pick up on it, in a good way. Want to make sure you knock your first-date outfit of of the park? Here are a few simple tips to help you slay.

1. Be yourself.

Just because your date has a bunch of tattoos and a mohawk in their profile photo doesn’t mean you should ditch your J. Crew wardrobe for some black lipstick, a chain mail t-shirt and a bunch of temporary tats. Your date agreed to go out with you based on what they already saw in your profile and conversations. So, just be yourself when it comes to your wardrobe choices. The last thing you want is to look like you purchased your first date outfit from Googie Rene’s Partially Damaged Halloween Costume Discount Basement.

2. Dress for the date activity.

Don’t show up wearing a three piece suit for a casual date at Starbucks and, for the love of jeebus, please resist the urge to don your favorite pair of hip waders to meet your date at a hip wine bar. This could be as simple as not wearing heels if you know you’re going to be going on a walk. Make sure you get a clear idea of where you’re going and what you’ll be doing so you can dress accordingly.

3. Be comfortable.

And no, I don’t mean wear that pair of sweatpants with the unidentified stain on them. While they’re the perfect garment for binge watching 18 hours of Game of Thrones, they’re not going to do you any favors in a date setting. Conversely, you don’t want to be wearing something that’s so constricting you spend half the date tugging and pulling on your clothing – like that super sexy bandage dress that looks amazing on you if you just wear three layers of Spanx and don’t breathe. First dates are stressful enough without having to worry about migrating elastic bands.

Instead, wear something that’s flattering and comfortable. For guys, maybe this means a clean, ironed dress shirt and your favorite pair of jeans. Ladies, this could mean some stretch denim and a cute shirt or your favorite dress & ankle boot combo. At the end of the day, you want to feel comfortable and confident.

4. Develop a few go-to date night looks.

Does getting dressed for a date stress you out to no end? To avoid mass panic, I suggest coming up with a handful of go-to date looks that you can put on in a pinch and feel your best. For example, I have 3-4 dresses that I specifically wear on dates because they’re just the right amount of dressy-meets-casual and I always feel good when I wear them. Throw on my favorite leather jacket and ankle boots and I’m set!

Also, don’t be afraid to accessorize. I try to always wear at least one piece of jewelry that I love and which feels really personal to me: for example, my gold necklace that’s shaped like the state of California (aka my happy place). If it comes with a good story that you can share, even better.

5. Don’t dig in the hamper for fashion inspiration.

Years ago, I agreed to go out with a guy I had met a few nights prior at an event. When we met, he was wearing a button down shirt, jeans and had his hair gelled in the style of a popular boy band member (it was the early 2000’s). He looked cute and polished. On our first date, he showed up wearing a pair of frayed jorts that looked on the verge of self-destruction, a Budweiser beer t-shirt and a pair of shower shoes with white sports socks underneath. His hair wasn’t styled and instead he had what looked like a serious case of hat head (the hat however, was nowhere to be seen.) He didn’t even look like the same person I’d met a few nights before. The moral of this story: don’t be this guy.

Although you may feel totally confident in an outfit pulled from the bottom of your closet, you’re going to feel even better and garner much better feedback from your date in something fresh, clean and ironed. You’re better than this. We all are.


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