What To Wear on a First Date: A Handy Guide for Men

You have been chatting online for a week and finally managed to find a time when you can both meet. You have set the location and are ready to go. All you need now is an outfit. While it might not seem that important, how you look will make a big impact on your date. Whether you like it or not, first impressions count, so you want to make sure your date gets the best version of you possible.

After two years locked away at home, you probably need to sort out your wardrobe. Your usual home attire of sweatpants and a hoodie just won’t cut it in the real world. Thankfully for you, we are here to help you out. We’ve assembled a handy list of tips and tricks to make sure you are dressed to the nines so your date will be super impressed from the get-go.

Things To Consider Before Choosing Your Outfit

Before you decide what it is you need to wear, there are a few things you need to take into account. Think about the situation and location and what is going to suit the occasion. Below is a brief overview of the factors to consider before picking out your all important outfit when going on a first date.

Think About the Location

If you are attending a fancy restaurant that has a strict dress code then you are better off not rocking up in jeans and a t-shirt. Likewise, if you are just grabbing a couple of beers at your local watering hole then a tuxedo is probably not going to impress your lady. The location has a big impact on what you are going to wear. Whether it is a walk on the beach, dinner at a high-class restaurant, or beers at the local dive bar, remember to dress for the occasion and keep your personal style intact.

Think About the Time of Day

You don’t want to be caught out wearing shorts when you should be rocking pants. The timing of your date plays a big part in what you wear. A date at the beach calls for shorts and a tee, while a few bottles at your local wine bar is better suited to jeans and a nice shirt or polo. If you are coming after work, you might want to lose the tie and blazer and roll up your shirt sleeves. Nobody wants to go on a date with a business bro at a funky hipster cocktail bar. Just be mindful of when you are catching up.

Take the Other Person Into Account

Don’t think you have to change your style because of someone else, but do take into account how they dress. If they are a little on the conservative side, don’t wear anything too revealing, like a half-open shirt or tight leather pants.

Fit Is Super Important

Wear clothes that fit your body type. This might seem like information everyone knows, but you would be surprised by the number of guys who wear ill-fitting clothes. You want clothes that accentuate your body and play to your strengths. There is no point wearing a tight tee if you have a bit of a belly or no upper body to show off. You also don’t want to be swimming in your clothes. Make sure your clothes fit before committing to any outfit.

Grooming Is Also Important

Along with your outfit, the first thing your date will concentrate on is your face. It is important that your appearance matches your outfit. Don’t go to a date with a scraggly beard, uncombed mop of hair, and bad breath. Be sure to keep your facial hair trim, your hair washed and styled, and your breath smelling minty. Trim your fingernails too. Grooming is just as crucial to your look as your outfit.

Style Dos and Don’ts

When it comes to what you should wear, there are a plethora of clothing options that work and just as many that don’t. There are a number of things to keep in mind before you head out on your date. To make sure you are looking your best and ready to impress, here is a list of the best dos and don’ts when it comes to organizing your first date outfit.

Dos

• Wear neutral colors. Blue, black, beige, gray, white, and cream are great neutral colors that combine well. These colors won’t overwhelm your clothing choices nor will they become a talking point, possibly for the worst. Your date probably won’t be impressed by a gaudy pink jacket. Also, keep your pants neutral. Dark jeans or slacks are always a good option.
• Shoes maketh the man. You might not think they are a big deal, but your shoes tell a lot about who you are. They are an extension of your personality. Wear shoes that match your outfit. If you’re going someplace nice, pull on a pair of Chelsea boots or brogues. Make sure they are polished. Going someplace more casual, then slip on a pair of canvas sneakers or white trainers.
• Wear nice underwear. You never know how well the date is going to go, so if you end up taking things further than imagined, you don’t want to be caught with your pants down, literally. High-quality underwear shows you care about your entire look, not just the clothes on the outside. A sweet pair of briefs or boxers will suffice.
• Wear a watch. Men don’t have as many options when it comes to accessories as women. This reason alone is good enough to strap a timepiece on your wrist. It doesn’t have to be a Patke Philipe either. Just a modern looking watch will add a touch of class to any outfit and could even be a talking point if your date likes watches.
• Add a splash of cologne. Women love a man who smells good, just don’t go overboard. There is no need to spray half a bottle of cologne on yourself before leaving home. Just dab a bit on your neck and wrists and you will be good to go.
• Keep the beard trim. If you have facial hair be sure to give your beard or mustache a nice trim. You don’t want to look like you’ve just spent six months in the mountains unless that is what she is into.
• Iron your shirt. I know, you probably don’t think this matters, but a crisp shirt makes such a difference. If you roll into your date with a crumpled shirt looking like you just got out of bed, your date will have already formed an opinion about you and your style choices before you even get to have a proper chat.

Don’ts

• No sunglasses, please. It doesn’t matter if it is a sunny day, wearing sunglasses on a date is just cringe. It also means she can’t look into your eyes and won’t be able to tell what you are really thinking.
• No hats either. Similar to sunglasses, hats on dates are just a big no-no. While you might think it makes you look cool and stand out from the crowd, she is probably thinking about whether you are going bald or not. Put the mystery to bed and go hatless.
• Wear shoes not flip flops or slides. This should be obvious, but wearing open-toed shoes is a big mistake. For starters, nobody wants to see your feet. Secondly, they are too relaxed. Even if your date is at the beach or it is a warm day, cop a pair of boat shoes or loafers if you want something summery yet fashionable.
• Stay away from bold logos and patterns. You don’t want your clothing to overpower your personality. For this reason, leave any bold prints, crazy patterns, or large logo tees at home.
• No hoodies. Hoodies are meant for wearing when curled up on the couch watching a movie, not when meeting someone for the first time. Your date will also think you put in limited effort if you rock a hoodie. Not the first impression you want to make. This also extends to sweatpants. Just no.
• Leave the suits for the office. There is really never a reason to ever wear a suit on a date. It screams formality and makes you appear snobbish. The only time you can consider wearing one is if you are coming straight from the office. If that is the case, ditch the tie and blazer and roll up the sleeves so you don’t look so business-like.

What To Wear on a First Date

So we’ve given you a few pointers on the dos and don’ts of what to wear, now it is time to provide you with some actual outfit ideas. There are several factors you have to take into account, such as the time of day and whether you will be doing an activity or just knocking back a few drinks. Once you have established the time, and place, you can go about picking what clothes suit you best.

Coffee Date

If you are just meeting up for a coffee, you don’t need to go overboard with your outfit. Most coffee catch-ups are shorter than other dates so while you have less time to impress, it doesn’t mean you need to overdress. A pair of chinos with a nice shirt or polo is a great start. As for shoes, a pair of white trainers will suffice. This is a casual look that still shows you put in the effort. If the weather is a little chilly, layer with a lightweight jacket.

• Top: Collared shirt or polo, neutral colors
• Pants: Chinos or jeans
• Shoes: Sneakers or loafers
• Outerwear: Lightweight jacket
• Accessories: Watch

Bar Date

Going from the coffee shop to the bar isn’t a great step up in regards to your clothing choices. You just need to make a few subtle changes. You can stick with chinos, but instead of the standard beige, go for blue or green. Jeans are also recommended. What style is totally up to you, but skinny jeans are on the way out, so aim for a nice tapered fit. For your top, you can stick with a collared shirt or polo. If you are going somewhere casual like a pub, even a crisp white tee will suffice. Depending on the weather, a denim or bomber jacket is a great addition. Pair with clean sneakers or boots.

• Top: Collared shirt, polo, or crisp white t-shirt
• Pants: Navy/green chinos or tapered jeans
• Shoes: Sneakers or Chelsea/combat boots
• Outerwear: Denim or bomber jacket
• Accessories: Watch

Day Date

Maybe you are skipping the cafe or bar for a picnic or a stroll through the park. This doesn’t require a massive change from the outfits described above. You can pretty much wear either, although a polo or t-shirt is better than a shirt. Likewise, you only need a pair of kicks rather than a chunky boot. If it is cold you can go with a lightweight jacket option or a parka if it is freezing.

• Top: Polo or t-shirt
• Pants: Chinos or jeans
• Shoes: Sneakers
• Outerwear: Lightweight jacket or parka

Dinner Date

Now it is time to lift your game. You can pretty much wear what you would to a bar date, just with a few tweaks. Wearing some kind of collared top is important, be that a polo or a nice crisp shirt. We suggest a neutral color collared shirt. Leave the jeans at home and go for chinos or a nice pair of trousers. This is the best time to wear a blazer if it is a bit chilly. For shoes, some form of a dress shoe, like an Oxford or bogue is best. Even a Chelsea boot can suffice. Don’t wear a suit though, especially with a tie. It is too formal and gives off the wrong impression.

• Top: Collared shirt, neutral colors
• Pants: Chinos or trousers
• Shoes: Dress shoes such as Oxford or brogue, Chelsea boots
• Outerwear: Blazer
• Accessories: Watch, nice belt

Outdoor Date

Just because you are outdoors and taking part in an activity doesn’t mean you can throw style out the window. You can still look good while being active and impress your date. If the weather is warm and you plan on going for a hike, a pair of shorts and a t-shirt are perfectly acceptable. As are trainers or sneakers. This is also the one occasion when wearing a cap is ok, just make sure she shes you without it so she knows you aren’t trying to find anything.

If it is during the colder months, you can still get away with chinos or jeans, although it might be better you wear a pair of flexible pants, although try and stay away from sweatpants. A sweater or sports jacket is also great to keep you warm. Similar to warm weather, a pair of sneakers is fine.

• Top: T-shirt
• Pants: Chinos, jeans, or pants
• Shoes: Sneakers or trainers
• Outerwear: Lightweight sports jacket or sweater
• Accessories: Cap

Above All, Be Confident

Whatever you decide to wear, do so with confidence and flair. You have to trust in your style and the clothes you wear. If you think you look good, you will feel good and this will come across when talking with your date. If you are constantly worrying if your shirt fits or if you chose the right shoes, it will affect your confidence. Have faith in your style and rock it with confidence. Your date will no doubt be impressed and you might even get a pash at the end of the night.

Conclusion

At the end of the day, whatever you decide to wear is totally up to you. While we think our suggestions are helpful and could transform an ordinary outfit into a fantastic one, you should dress in what you feel comfortable wearing. As long as it is a true representation of who you are, that is all that really matters. Being authentic is a big part of dating. You want to show your true persona, the real you. If your date isn’t feeling your style it is her loss.