Ultimate Guide to Dressing for a Date

There are enough things to be stressed about on that first date. Where to go? Will you hit it off? What if you say something stupid? This guide will help ensure that you can check off worrying about what to wear. Here is a comprehensive guide for what to wear on your first few dates, and what to wear in specific dating scenarios, as well as how to choose quality pieces while building your wardrobe. 

First Date Styles That Are Sure To Impress:

The first date is your chance to pitch yourself. So you want to make sure you are looking your best. Do not be afraid to make an extra effort. Looking like you tried, to a point, is actually flattering to your date and attractive. 

  • Fit is one of the most important elements in men’s clothing according to Men’s Health magazine after they interviewed hundreds of women. So start with making sure that all parts of your outfit actually fit your body. No matter your size or fitness level, the right size and fit to your body will make you look great. 
  • Wear your best boots with clean socks that compliment the color of your shirt. Nice shoes are a must on a date and don’t overlook details like socks because your date will likely notice them as well. 
  • Depending on the location of the date chose jeans or pants that are clean and well-fitting. If it is a casual setting go with jeans.
  • Top your jeans on a casual date with a quality button-up that is in a neutral color. If you do choose to go with a bold color lean toward red or darker shades. 
  • Do not forget cologne to draw her in subconsciously, but do not wear too much. 
  • Finish off the look with a quality watch. Any more jewelry is too much for a first date but a nice watch is the perfect finishing touch. 

Second Date Clothing Options That Will Turn Her Head, Again:

You have made it through the first date. You did something right because she agreed to meet you again. Now is the time to show that you are just as charming and attractive in a new situation and after several hours together. 

On this date, you can share a bit more of your personality in your clothing choice but still stick to the rules of making sure everything fits well, is clean, and non-tattered. You may end up getting a little more physically close on this date so be sure to remember cologne and clothes that smell clean and look great on your body. 

The Third Date and Beyond Style Tips: 

Do not stop trying just because you seem to have her hooked. Remember particular items of clothing she complimented and try to wear them on special occasions and even buy more in a similar style an color variations. 

The third date may be the right time to invest in something more than a casual dinner and movie, it may be time to show off your style in a fitted suit over a formal dinner. At this point, you will know your date well enough to have an idea of their idea of a good time so chose wisely. 

As your dates progress the below style guides about specific locations and situations will help guide your fashion to impress at each turn. 

 Dress Guide For Specific Dating Situations

Casual Dinner  – Do not take the term casual too literally. You want to look sharp and clean. You are off the hook when it comes to needing to wear a tie or suit jacket, but that does not mean to just phone it in. Start with a crisp button-up, white is a classic go-to but do not be afraid to go with a little color. Keep it short sleeved and casual. Add a pair of perfectly fitting jeans that do not have a single mark on them. This is not the place for faux rips and stains. Step it up just a bit. Wear flawlessly cleaned leather boots or even loafers with clean socks and you have a casual date attire that does not look like you went overboard. 

Formal Dinner – For a formal dinner with a girl you want to woo, do not be afraid to dress to impress. If you have reservations at a place that requires a jacket to enter, then go all out. Impress your date with your skill in rocking a tailor-fitted suit, because women do notice how a man’s body looks in a well-tailored pair of slacks and a suit jacket. Be sure to go the extra mile and shine your shoes. An extra tip: if you make formal dinner reservations be sure to tell your date in advance that it is a formal place, so she does not dress too casual and feel awkward. 

Meeting For Coffee – Here is a situation where you have just a bit of time to make an impression, you do not want to overdo it, but you do not want to look like you just rolled out of bed either. A pair of khakis with nice shoes and a polo shirt should do the trick in most cases. Think of it as dressing for a nice brunch. Be sure to keep your appearance and conversation on a date like this easy and casual with the slightest bit of formality. 

Hiking – If you are with a date who feels like hiking is their idea of a great time, you have many options for the perfect attire. First, go for mobility and comfort because if you can’t keep up with her it will sour the whole day for both of you. Second, there are many hiking clothing options that also look stylish. Go with a pair of khaki shorts or pants, a polo shirt, and invest in hiking boots if you do not already have a pair you can rely on. Make sure to walk around in your new boots for a few hours well before the date though, so you work out any issues before you are trying to prove yourself in the wild. 

After-Work Drinks – This is an upgrade from the morning coffee meeting but can still be cut short if things don’t go well. Win-win if you are not sure you will be into the person you are meeting. Help tip things in your favor by showing up with your A-game. Because it is later in the day when things often cool down, it may be a great opportunity to show off your boss leather jacket. Wear nice jeans, a sleek belt, a bold colored shirt, and a black leather jacket with a pair of matching boots that add to your height because it is likely she will show up to this date in heels herself. Keep it casual, and do not choose a place that is too noisy. If you hit it off well, you may want to move the date to dinner and more. 

Day-Date With No Specific Destination in Mind – If you do not know exactly what you might be doing because your date said they would plan it then stay on the side of overdressing but go for comfort. Think Sunday brunch meets a hike in the park. A nice pair of pants that you can move freely in, comfortable shoes that will also look good in a formal setting and a polo shirt will likely cover all of your bases. You may want to pack a pair of shorts and a t-shirt in case the date takes a more casual turn than you expect. 

Mystery Night Date – If your date is planning a night-time getaway but won’t reveal any details dress for a high-end dining experience but wear shoes you can dance in. A pair of dress slacks, nice boots, and a colored button-up shirt but without the tie and jacket will likely leave you confident if she shows you a night on the town no matter if you go to a local dive bar, an exclusive club, or a walk on the beach. 

Dinner and a Movie – This date is uber casual, but that does not mean no effort is required. Wear jeans and a nice shirt for this. You may choose to go with a tee for this date but make sure it is quality and not see-through, stained, or tattered. A nice polo shirt or a casual button-up may be a better choice, depending on the girl and the place you plan for dinner. If it is a local burger joint or pizza bistro, then go casual, but if you plan on mixing the casual movie with a formal eat-in situation, dress it up just a bit. A tip for a movie date is to put a sweater in the backseat of your car with your cologne on it. They often keep movie theatres cold, and you will have an opportunity to let her borrow it if she starts acting cold.  

Meeting Friends or Family – If your dates evolve to the point where you meet her friends or family, then you want to impress her and her loved ones all at once. It can be a precarious situation because you do not want to look like you tried too hard, but you also want to make a great impression. In this scenario, err on the side of formal but simply dress for the occasion. If it is a picnic at a local park, wear nice khakis and shoes you feel comfortable in if you need to catch a ball or stroll around the paths. Do not seclude your self with your date or take up all of her time, treat her friends and family like your own and you will make a great impression. 

The Beach Date – This is a perfect chance to be a little fashion-forward if it is comfortable for you. Brown boat shoes with khakis and a tropical or plain white button-up will look hot on a summer day. Remember your sunshades so you are not squinting at everything, and be sure to pack a pair of trending board shorts just in case she wants to take a dip in the ocean. 

Keep This Vital Information in Mind:

No matter how nice or expensive an item of clothing is, it won’t matter one bit if it does not fit you. You may be tempted to borrow your roommate’s expensive sweater, but if it is ill-fitting, you might as well be wearing anything else at all. The fit is the priority; a good fitting bargain item will elevate your appearance more than any other item that is too big or small. 

If an item of clothing is radically out of your comfort zone, you may not look as good in it because of your behavior. For example, if you go for a complete makeover before your date, you may end up feeling like an imposter all night and act less charming than you would otherwise. Make sure your pieces fit your personality as much as your body. This does not mean to shy away from trying new styles and items; it just means that you should try a new style on another day when you can get a feel for how you feel while wearing it. 

If you show up to your date’s home or the set location where you planned to meet and you are dressed very differently from each other, do not make a big deal out of it. Compliment whatever she chose to wear and, if needed, adjust your plans to fit her attire. Play it as cool as possible. The point is not only to impress your date, but it is also to get to know her in the most relaxed way possible so you must be able to go with the flow. 

Clothes Make the Man

Shakespeare said: “cloths oft proclaim the man” and Mark Twain is quoted as declaring: “Clothes make a man. Naked people have little or no influence on society. 

There is no debating that dressing well is an important life skill that can increase your chances of landing your dream job, winning friends, and even getting the attention of your crush.

Whether it is your first, tenth, or thousandth date, you want to make the best impression on your crush without looking like a try-hard. The secret to date attire that others will want to duplicate and your crush will find irresistible is to mix three components, your personality, comfort, and style. Read on for a list of six essentials you should not overlook if you want to look your best.

The Essentials Will Make You Feel Like a Million Bucks

  1. High-quality jeans that fit your body just right. Take your time finding a brand that works with your body type. When you do find that perfect-fitting pair of jeans, buy as many pairs as you can afford because they are the base of many styles and well-fitting jeans can be hard to find. 
  2. A leather jacket that makes you feel confident. If you are vegan, then you can go with a faux-leather jacket or a thick knit sweater, but a high-dollar item to wear when the weather gets chilly will bring out the confidence in you that is more appealing than anything else. 
  3. Shoes that are both comfortable and stylish. You do not want to look pained on your date, so be sure to wear a pair of comfortable shoes. However, also balance comfort with a pair that look stylish and not too worn. Boots are a great option because most add an inch or two of height, which is always a plus for confidence. 
  4. A fresh hair cut and a shave. Even if you choose to wear your hair longer or have a full beard, you can still benefit from time in the barber chair before your date. A beard can have clean lines, and longer hair will look nicer with a trim. Anyone who is clean-shaven with short hair knows the confidence boost that comes with a nice haircut. Just be sure not to go with a new barber before a date, stick with the tried and true.  
  5. Quality Cologne in Moderation. After taking the time to pick the perfect scent and be sure to wear it on every date, but not too much. A spray on the inside of your shirt and on your pulse point is more than enough for subtle sex appeal. 
  6. A Watch That is Clean and Not Cheap. A man wearing a watch looks like a man whose time is valuable, and a man who is stylish and confident enough to wear jewelry. Find a quality timepiece within your budget at all stages of life. Be sure to have any jewelry you wear cleaned often. 

Leave This At Home if You Want Your Date to Swoon

Any item of clothing that has not been worn in the past for at least an hour should be left for another day. It is not uncommon to pick up something new and nice for a date when you want to impress. However, it is a good idea to wear this new item and make sure you feel comfortable in it before your date. If you are walking funny because new shoes give you a blister or the shirt you thought was top quality turns out to be an unraveling mess then your date cannot get to know the real you. 

Now That You Know What To Wear to Impress Your Date, How Do You Start to Build Your Wardrobe? 

You can build a great closet no matter your budget if you shop smart and know what you want. Use this guide to start your collection using the rule of quality over quantity, and fit matters more than brand. The key to a quality versatile wardrobe is taking your time, shopping around, and knowing what you like. 

Do not be afraid to spend a few hundred dollars on a good jacket because the quality will be apparent every time you wear it, but more importantly, this item should last you many years. A good piece of clothing is one that can be worn for more than one season and a jacket, quality boots, a fitted suit, and even some brands of blue jeans are an example of being worth the extra bit because they will last you a long time. 

You can add to your wardrobe a piece at a time. Do not feel bad if you can not fit in a shopping spree, just choose nice pieces from shops, and online stores each time your budget allows. Aim for an item each month. Remember to update things like socks and underwear often because dingy socks peaking up over quality shoes is not attractive. 

One item you may need to save for but will be worth every penny and even open doors of opportunity is a custom suit. A suit should be worn by a man, but so many men look like their suits wear them because they are so ill-fitting. A custom suit will make you look irresistible, confident, and in charge. Splurge here even if you have to budget in other areas for a few weeks. 

A how-to guide for adding to your collection will help you continue to attract people into your life on first impressions and continue to impress your date even after you have been together for a long time. 

Dating Should Be Fun, Get The Basics Down Then Relax! 

Now you have all the information you need to dress for dating success. Do not worry if you do not have every item mentioned; just use this as a guideline with the items in your closet currently and add to your collection as you go. Always remember to start with a shower, brush your teeth, and go in with a positive attitude. You do not have to be the most handsome or the richest man around, you just have to put in basic effort in your appearance and try to have a nice time, and you will have a long term love or serial dates every single weekend.