Date Night: What to Wear?


by Maria Vasiliadis

Dating is hard. Putting aside nerves, wondering what he thinks, and figuring out what you should/should not say all cause enough stress. But deciding what to wear on a date can be Date Night Outfitsjust as difficult, if not more difficult, than having a great date altogether. An outfit can make or break the entire direction of the rendezvous. And while it’s true that what you wear is your first chance to make a great impression, that's not the main reason the outfit can make or break the date. What you wear and how you feel about your appearance are what can greatly affect the encounter. After all, when you’re comfortable and confident, your personality will have it’s time to shine. The rest is up to him.

As discussed, date night is the kind of night where you want to look good so that you can feel good. You are getting to know a new person and they are getting to know you. One of the ways that this is done is by observing one's personal style. Personal style is important because it is a huge indicator of a person’s interests, lifestyle, and getting a glimpse of their overall vibe. When you feel good, you feel comfortable, and when you feel comfortable, you will be able to put your focus on getting to know your potential suitor.

Date Night Fashion Choices ClosetOften times figuring out where you should start in your closet is the most difficult part, so answer the following five questions to give yourself a head start and guide you in determining the perfect outfit for your date:

If you ask any girlfriend who knows what she is talking about what you should wear on your big date, the first thing she will say (like I said, if she knows what she is talking about) is:

Question #1. Where are you going?

This is ultimately where the journey on deciding what to wear on a date begins. Do not try and pick an outfit until you know the locale and events of the evening. This means that if you have no idea, do not be shy to ask, and if your guy will not tell you, for some romantic reason, then straight up ask what you should wear. He will appreciate that you are putting thought into the date and be honest in his response, even if he has no idea what he is talking about. He, also, wants you to look and feel good, so he should be helpful. Dressing inappropriately for an event can make you feel like your experience has been ruined before the date has even begun, so be certain of what you are getting yourself into to avoid this type of situation. Again, remember that date night outfits for the single lady are ones that make you feel great. The confident vibes you emit will radiate, and your guy will respond positively. Inappropriate attire will, obviously, have the opposite effect.

Ideas to Consider:Female in Ball Cap

It doesn’t take a rocket scientist to realize that the more casual events would require the more casual ensemble. For example, men love their sports, and a trip to the ballpark can be a great opportunity to show your fun yet feminine side. Jeans always pair perfectly for sporting events, and a cute pair of sneakers complement the outfit and event perfectly. If you are not into sneakers, a simple flat shoe or sandal serve the same purpose. Jeans will allow you to be comfortable and will not pose problems if outdoors and the wind starts blowing. Think soft and cotton materials. A flirty cotton dress with a jean jacket and sneakers would make for a perfectly cute and fun outfit. A ball cap in support of your suitor’s favorite team can help earn some brownie points. Just be sure your look is still on the feminine side. Remember you’re his date, not his drinking buddy.

Then again, speaking of drinking buddies, maybe you’re out for a night of cocktails and fun. Getting your drink on can be the perfect time to unleash and loose your sexy side. Let your own comfort levels with sex appeal guide you in your choices. Anything that is too out of your comfort zone will make you feel awkward and out of character and your guy will be able to sense this. Nighttime drinks are a perfect time to show some skin (but not too much). Show some legs with a fun, flirty dress, they call them cocktail dresses for a reason. Or, wear pants with a shirt exposing your collar bones and arms if the weather is too

chilly for leg exposure. Dresses are a great option because they not only show off the shape of your legs in the summer but can do the same in colder weather with tights and booties during the winter months. A jacket that completes the outfit in the spring or cool summer nights could be worn with a dress as well. Stay away from cotton, jeans, and other soft fabrics when going out on the town. Materials with a lot of movement are flirtatious and fun and would work perfectly for a night at the bar. Just don’t overdo the booze, no matter how cute the outfit, a sloppy drunk makes for a lousy date.

A weekday dinner date most likely means that you have had a chance to go home before your rendezvous. Take advantage of this brief opportunity. A full outfit change is not required, but having the opportunity to freshen up is one that should be taken advantage of. If you were feeling a bit un-fresh from the day’s work, swap out a new shirt at the very least. Since it will now be nighttime, and therefore dark out, your attire should be slightly vamped up from the day. Soft and cotton materials are still acceptable, but intensify a casual outfit with accessories. Gold and silver jewelry are always classy and classic, but a bold bag or necklace can work as well. In the summertime, an evening dinner should not show too much skin, so if you are leaning towards a dress, try a jean jacket on top.

If he is taking you to an upscale, expensive restaurant, you yourself should look up-scale and a bit more extravagant. There’s nothing more perfect than a conservative and classy dress made out of a rich fabric to wear to a dinner your beau had to make reservations for weeks in advance (or even if just a few days). If it's a special event or a truly elegant or exclusive locale, the event may call for an enticing evening dress or chic new sequined gown.

Question #2. How formal is the date?

Knowing and understanding the level of formality of your date is important because this is what makes a girl look like she is confident, aware, and comfortable in any situation. The day of the week and the time of day play a large part in deciding the formality of the date. Any date on a Friday or Saturday night should involve some sort of heel, even if one inch, and weekends should typically be dressed up a bit more than weekdays. Wedges during a weekday dinner work great. Wedges are also a perfect choice for when you may have any uncertainties regarding the formality of the date. The wedge provides the casual-factor while the heel provides the dressy-factor, so a little bit of both can allow you to go either way.

If you have any other uncertainties, dresses are safe for more formal occasions while pants are more appropriate for casual. Short shorts should only be worn casually or to a nightclub when the temperature is scorching hot, though skirts can either give a cute, classy, or professional look, depending on which effect you desire.

Ideas to Consider:

Be able to distinguish between casual and classy events by thinking about the setting and the people that will be around you. Figure out the answer to this question by asking yourself:

Question #3. What is the date environment?

Knowing the environment of the date takes into account the people that will be surrounding you during the date. This could range from just you and your suitor, to just a few friends, to thousands of people. Dates held at home, where no other person is around, are usually more casual and intimate. So, dress in a comfortable way that shows off your personality and personal style. Jeans are always a comfortable choice, but a maxi dress in the summertime will allow you to be feminine, flirty, and have maximum comfort all at once. Also, just as a reminder, if you are going to be home alone, be sure to think about the status of your pedicure. If the thought of being barefoot around a new guy makes you nervous, either fix the problem or structure your outfit on the ability to wear a shoe that requires socks (sneakers, boots, or another type of laced shoe).

If you are going somewhere your guy’s friends will be, make sure you do not look like you are trying too hard. You want his friends to think you are cool, and they will think this if they do not think you are trying too hard to impress their friend. With that being said, do not reveal too much skin or try anything too risqué. When you score points with your guy’s friends, you score points with your guy.

Romantic Date Kiss HandPublic dates amongst strangers are a great opportunity for your man to show you off. With that being said, wear something that is worth putting on display! This is a great time to dig deep into your personal fashion and wear something that screams you. Wear your favorite fashion trend of the moment so that you call the most positive attention to yourself through just your presence alone. There is no better time to show off your latest purchase or favorite item then when you are out and about, and your guy will love your call to style. Do not be afraid to refer to the latest fashion magazines and blogs (right here works) to inspire your cool and trendy date outfit. A little inspiration can always help in making the right choice.

The environment of a date sometimes depends on the time of day the date is taking place, which is why you must also consider:

Question #4. When is the date?Kissing on Date

Weekdays are obviously more casual than weekends. With school and work taking place on weekdays, everyone understands that these days are busy with the hustle and bustle of everyday life. All of this should be considered when planning a date outfit. A dinner date before 7 pm falls within the time frame that it is acceptable to look like you just got out of work because after all, you did. With that said, whatever was worn during the work day is acceptable if working an office job. If going to a casual dinner spot, swap any office heels with flats or sandals. If working in a casual environment, make sure to tailor yourself to wherever you go. Dress up a super casual outfit with a low wedge heel or a structured jacket or blazer.

Planning a day-to-night outfit also becomes crucial if a stop at home before your date isn’t possible. With that in mind, wear something that you know you can go for hours in. Work dresses are always the best option when planning a day-to-night outfit because they are the most versatile. Dress down a dress with a jean jacket, or dress it up with a set of pearls and nude heels. The extra-value added with a dress is that it is also the most comfortable item in the closet! By giving your body openness and the ability to breathe and move, you will still be feeling fresh come 5 o’clock.

To ensure you are feeling you are freshest at the end of the workday before you go out, an important question to consider is:

Question #5. What will the weather be like?

This question is a question that is often overlooked, but it is so important that it could make or break your ability to look and/or feel good. Always make sure to check the weather forecast hours before the date (or days, if it's that important)! The worst feeling is to feel uncomfortable on a date. If you are uncomfortable, you will not be able to enjoy the date and in turn, neither will your man.

Ideas to Consider:

If there is a chance of rain, avoid leg and foot exposure. Stick to rain boots or waterproof flats or sneakers. There’s no worse feeling than soggy feet, and if you do end up with them, going to his (or your) place after the date will be impossible without any sort of mortification. If there is a sign of severe thunderstorms, do not be shy to cancel, especially if the majority of the date was going to be spent outdoors or walking.

Love Dating Rainfall Storm Kissing In the rain may be romantic but be sure to be dressed for the occasion.

If the day is going to be windy, wear anything but a dress or skirt. Keep a jacket or cardigan in the car and try to style your outfit around a ponytail or bun. These hairstyles will prevent any hair dysfunction on a windy day could cause.

Nighttime during certain seasons can get chilly, so always be prepared with a jacket option if the temperature will drop. Or, wear a long sleeve shirt with pants; this outfit will ensure that you stay cool during the day and warm at night from the extra skin coverage.

In the summer, dresses are almost always a good choice because they not only look cute and show off your legs, but they allow you to feel comfortable and cool, even when it's scorching hot out. Your date will appreciate some subtle skin, and you will appreciate your level of comfort.

Final Advice to Consider:

Dating should be fun and flirtatious. With that said, a perfect place to begin your flirting is with your fashion choices. This is the easiest way to tease, tantalize, and seduce without even having to say a word. Stay away from outfits that have too much male inspiration, such as slacks, collars, and boxy cut tops. Limit yourself to one masculine feature if you insist, and then try to accentuate a feminine part of your body. For example, if your top has a collar, then a skirt or dress underneath to show off your legs is a perfect choice for pairing.

If you have just started dating a guy, do not dress in ways that look like you are trying too hard. Effortless beauty is something your guy will admire and love about you, so often times keeping it simple is better. If accessorizing is your thing, be sure not to overdo it. Keep makeup to a minimum as well. You want your guy to see you for who you are, just the way you are, and this is the way he wants to see you too! Do not hide behind a shield of makeup.

If you and your man have been dating a while, he knows who you are, what you look like, and what your style is. With that said, now is the time to start experimenting with your dating fashion. Go for a dark smokey eye on the weekend, something you might have avoided on your first few dates. This will come as a pleasant surprise and will keep your guy pleasantly intrigued as he continues to learn more about your personal style. Try a bold lipstick on a weekday for the same effect.

At the end of the day, the best and most appropriate outfit for a date is whatever makes you feel like the best version of yourself. Your confidence is crucial. If you are feeling confident, you will allow yourself to open up to the date and the guy you are with so that you can fully express who you are, both inside and out. Being comfortable and confident will allow you not only to have the most fun but to focus on learning more about the guy you are with. After all, it’s a two-way street. If he shows up in jean shorts and a pair of crocs, don’t hesitate to slam the door in his face. He should have read his own article.


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