What To Wear on a First Date: Tips for Eligible Bachelors

First dates are intimidating. You want to make a good impression, and, for better or worse, many first impressions are made on what you’re wearing. Your choice of outfit is also a huge indicator of your personality, and you want to express the right one. If they’re going to keep your dating history to one outing, you don’t want it to be because of something you wore. With more styles available than ever before, it’s hard to know what to wear and what looks good.

Plus, if you’ve been working from home for nearly two years, your wardrobe might consist of mostly sweatpants, which isn’t exactly first date material. We’ve assembled fool-proof tricks to create and elevate any first date look, helping you make a great first impression and secure a second date before the night is over.

It’s All About the Venue

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Consider dressing for a first date the way you would any other event. And what’s the first question you ask yourself when choosing an outfit – “where am I going?” Just as you wouldn’t wear a tuxedo to a farm or overalls to an opera house, don’t miss-dress for the first date venue. 

Where did you and your date decide to go? Supper at a local low-key restaurant, coffee, or a walk through a nearby park calls for casual wear. Something you feel confident and presentable in, but would feel uncomfortable wearing to a gala. There’s no need to over-dress. This isn’t a job interview, it’s a date. Wear something you feel relaxed in. 

If you and your date are attending something more formal or higher-brow, consider a dressier look. A friend’s wedding, tickets to an off-Broadway production, or reservations for two at a Michelin-star restaurant calls for upscale clothing to match the upscale vibes. Don’t wear the same outfit you wore to work that day, unless, of course, you work in a very formal environment or had an important meeting that day. Go for something sleek and smart that shows you can dress for any occasion. 

Consider the Time of Day

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Once you’ve established the venue, consider the time of day. Your outfit is going to look much different for a sunset breakfast than a midnight drink. Consider the time of day like you would the overall vibe when choosing an outfit.

Spoiler alert: a tuxedo does not fit the morning, and pajamas do not fit the evening. It may seem like an unnecessary consideration, but it’s not. Even at five-star restaurants, a daytime outfit reads differently than an evening outfit, and you’ve got to know the difference. Wear an outfit appropriate for the time of day. 

Shoes Are Important

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Shoes are shoes are shoes, right? Wrong. Shoes are just as key to an outfit as clothes. They express personal style and send messages to your date. Think of it this way – if you arrive wearing clown shoes, people are going to think you’re a clown. And the last thing you want your date to think of you as is a clown. Wear proper shoes that match your outfit and fit whatever you’re doing on your date. 

For a casual date, a pair of nice sneakers or casual loafers will suffice. If you’re doing something more upscale, wear dress shoes with laces. Dress to impress. Don’t arrive at a swanky restaurant in Air Force 1s. 

Groom

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Grooming is highly individual, but a few standards can help you decide which route to take. When choosing how to groom for a first date consider some things: how did you look when you and your date met? Will they be jarred to see you with a clean face after meeting you with a full beard? Keep your look similar to your first interaction.

If you’ve met multiple times before going on a date, choose a look you’re comfortable with, but tend to it. Don’t arrive at your date with patchy facial hair because you were too lazy to shave, or pull your hair into a bun because you missed your appointment. Be intentional about your grooming habits pre-date, and put some thought into your look. 

Remember, grooming covers the entire body – not just your head. What’s the vibe? Will your date be down for a sleepover afterward? If so, be prepared. Groom according to your comfort level. Whether it’s smooth as a baby’s bottom or unkempt as a jungle, be confident in how you’re presenting yourself to your date if the clothes come off. 

Be Confident

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Nothing is more attractive than confidence, especially when it’s warranted. A man who knows himself and is confident in how he presents himself is undeniably sexy and translates well to a first date. Show your partner or potential partner you’re comfortable with yourself and have arrived dressed in an outfit you love. 

If you’re uncomfortable with your outfit, change. On a first date, you want to display genuine confidence, not the manufactured kind you fake for an important business deal. If you’re uncomfortable in your clothing, you won’t be authentically confident. 

Comfort in clothes is different for everybody. It can be physical comfort from the material of the clothing, or emotional comfort – something you feel good in and know you look good in. Determine what you feel best in, both physically and emotionally, and wear it. This isn’t to say you should wear khaki pants to the beach – don’t be a weirdo. But if you’d rather wear slacks than denim, by all means. As long as you aren’t going to look out of place, wear what makes you feel your best. 

Be Yourself

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Many things are important on a first date, but atop the list is being yourself. You’re on a date for a reason – you’re getting to know each other and starting to determine whether this relationship has long-term potential. To learn whether or not you and your date are compatible, you must be yourself, and that includes what you wear.

It’s easy to write off clothing as a superficial part of life, but there’s so much to learn from even a single outfit a person wears. If you wear something completely out of the ordinary, you risk miscommunicating with your date, leading them to believe something entirely different about you.

Don’t feel you can’t buy a new outfit to wear – new outfits can give us confidence and make us excited about an opportunity to wear them. But choose something you’d wear regardless, not just on a first date. 

But being yourself isn’t an excuse to sport a sloppy look, though. That restaurant you’ve been trying to get into for months won’t let you in with joggers and a hoodie on account of being yourself, and your date won’t be impressed by your lack of effort. Effort is just as sexy as authenticity. 

Must-Try Date Looks

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You didn’t think we’d leave you without specific date look options, did you? Of course not. We’re here to help you delete Tinder, not sabotage your first date. We’ve put together suggestions for looks to wear on four different styles of first dates to help you snag a second, and have your partner describing you to all their friends as “well dressed.”

A Sporty Date Look

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Your first date activity might be something sporty, requiring you to move and stay on your feet, like mini-golf or an amusement park. For these dates, keep material in mind. Opt for something breathable like cotton shorts or pants. They’ll look good, keep you from sweating (no one wants swamp ass on a first date), and be easy to move in.

For a top, again consider how much you might sweat. Depending on the weather, wear a short-sleeve T-shirt, or a lightweight sweater in a dark color. Avoid gray or tan, and go for black if you’re at all worried about pit stains.

Don’t wear a shirt that’s too constricting and limits your movement, and choose shoes that are comfortable to wear while standing for a long period of time. Sneakers or tennis shoes are completely acceptable on a sporty date. 

A Casual Date Look

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Casual dates are the ones at laid-back venues like coffee shops and parks. You aren’t expected to be dressed to the nines, but it’s still important to be put together. For a casual date, forego shorts, even if it’s hot out. If it’s too hot, schedule your date for the evening when it’s cooled off a bit. Shorts are too casual. You can choose between denim or casual trouser, something with a skinny leg and a typical color, like olive or gray. 

Choose your top according to the climate. If it’s snowing outside, your favorite sweater is a perfect option. If it’s sunny and 75, a colored t-shirt will complete your look perfectly. For weather somewhere in between, layer a leather or denim jacket on a t-shirt for effortless vibes. Avoid tank tops at all costs. 

For shoes, try something relaxed like Converse sneakers or casual Oxford loafers. When it comes to shoes, much of the dressiness is based on material, so suede or cloth is the way to go for a casual date. Like tank tops, avoid sandals. Only wear sandals to the beach, unless you don’t want a second date. 

A Business Casual Date Look

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Sometimes dates are scheduled for the middle of the week, in the middle of a workday, or immediately after the workday is done. This isn’t common, but it happens, and you need to be prepared if it does. Luckily, this is an easy look to achieve. It’s basically what you’d wear to work, but on the days you have an important meeting or presentation. 

On important days at work, you’re trying to impress someone, just like you are on a first date. A pressed shirt and a good looking sport jacket are the easiest way to impress someone. Keep your bottoms dressy as well. If you can, schedule your big presentation for the same day as your first date. Two birds, one handsome stone. 

A Dressy Date Look

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Like business casual, dressy is a rarity in date looks. It’s not often you attend an opera or a charity gala on a first date, but it could happen. A tuxedo is probably not necessary, but a three-piece suit, or at the very least, a suit jacket, is required, as is a tie. And if you don’t know how to tie a tie, find a tutorial on YouTube. 

Accessories make or break a dressy outfit, so wear your best watch, tie clip, and matching pocket square to complete the look. You’re sure to get a second date. If not, you’ll get another first date with someone else for sure.