If a guy asks you out, do you spend most of your energy planning what to wear on a date? The right date outfit ensures that you´re going to enjoy the date.
Dating can be a wonderful experience. You meet new people, you learn new things, and you get the chance to meet the love of your life. But dating can also be stressful and exhausting. The highs and lows of emotions, the fears, the disappointments, and the inevitable stress of the process contribute to what feels like a rollercoaster ride in dating.
But although you can´t control how a date will turn out, you can minimize the stress of preparing for a date.
Have you ever found yourself panicking because you don´t know what to wear to a date and the date is in an hour? Factor in the time to commute and you´re probably going to be late. Plus you don´t even know if you´re going to look good in any of the outfits scattered on your bed. Do you feel the stress?
Or you probably found yourself dateless for quite a while and your calendar still void of any romantic date schedules. What if a handsome man will out of nowhere ask you out on a date tomorrow, are you prepared?
Having an arsenal of style ideas on what to wear on a date comes handy when it´s time for cupid to shoot the bow. And you´d want cupid to shoot that bow straight into his heart, right?
So choosing an outfit to wear to a date is important. You don´t want to just look good, you also want to appeal to his masculinity. Which means, your aim is to embrace your femininity.
Sure you can also wear those tailored pants and suit to a date … straight from the office. But remember, you´re going on a date. Not to a business meeting. This is the time for you to be a girl.
Tips on Choosing What to Wear On a Date
When you are asked out on a date, he may ask you for a daytime date or a night date. Maybe it´s the first time that he asks you out, or the second, third, or fourth time.
The time and the venue of the date matter in choosing an outfit. But whether it´s a first date or a getting-to-know-each-other-more kind of a date is another factor to consider in choosing what to wear on a date.
For first dates the venue is preferably low-key. This takes the pressure off you and him. He won´t be pressured to pay for an expensive dinner, which can be disappointing if the date doesn´t turn out well.
As for you, you won´t feel pressured to impress or perform, nor will you feel pressured to accept his second date invitation if you don´t feel like it, just because he took you to an expensive venue for your first date.
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It´s important to remember that the date outfits for first dates should be natural and effortless. This relates to the idea that the first date itself must be low-key.
Your outfit must not look forced or something that makes you look like you´re trying-too-hard. Later, you can increase the effort as he takes you on more dates. In the same way, he can increase his efforts in taking you to more expensive and elegant venues as you both invest more time and energy into getting to know each other.
How to Choose the Right High-Low Style Dress
For today´s style guide, I decided to feature the high-low style dresses as Glee Approved date outfit pieces.
Whether it´s knee-length or ankle length, a high-low dress often has an A-line silhoutte that is feminine. The moment you slip into one, you automatically become girly. It also gives a hint of legs without overdoing it.
Now speaking of overdoing, in choosing a high-low dress you may want to pay attention to how high is the side or front slit of the dress. Avoid dresses with very high slit (such as this one) as they are prone to accidental flashes. You don´t want to do that especially on first dates.
You may also want to avoid dresses with too much ruffles (such as this one) or with floor-sweeping back hem (such as this one). They either look too heavy or too prom-ready. Your outfit should be fun and functional.
So here are the high-low dresses that I think will make for a perfect date outfit:
Dresses For Daytime Dates
Outfits for daytime dates can include bright or light colored pieces that are fun and flirty. They should be effortless and not over-the-top.
Showing a bit of skin is fine but you should do it one at a time. Is it the cleavage, the shoulders, or the legs that you want to highlight? Never show two or three goodies at the same time. It may send off the wrong message.
1. The Bright Orange Ruffled Midi Wrap Dress
There are three things that I like about this dress. First, it´s a midi. Its hem length lies between sexy (above-the-knee or knee-length) and formal (ankle length).
Second, it has a bright orange color which is youthful and upbeat. And third, its wrap-style and bow-tie are casual elements which make this dress just the perfect effortless dress you can wear to a first date.
2. The Yellow Ruffled High-Low Wrap Dress
If he is taking you out for a lunch at an exclusive restaurant, a bold colored dress is something to consider. The dress is airy and has fun feminine details such as the micro-ruffle detail along the V-neckline and the cute tying tank straps.
3. The Red Floral Print High Low Dress
Cute and feminine, a cheerful knee-length dress such as this red and white floral is perfect for a more casual type of date. Are you going out for a coffee or visiting a museum?
Remember that even if your casual date requires some walking, always wear the dress with high heels. Open-toe strap heels are made for high-low dresses.
4. The Red Striped Satin High-Low Midi Dress
This is my favorite among all the daytime date dresses I featured here. Striking is the word for it.
Did you know that bold colors such as red make a woman look more attractive? It´s gutsy. It channels your confidence. And it juxtaposes your femininity with assertiveness.
Wear the dress with matching red-strapped high heels. Click the link under the photo to see the heels that the model is wearing. So gorgeous!
5. The Blue Floral Print Midi Dress
If you´d rather not wear bright colors, you can opt for prints instead. The white florals on blue on this dress is subtle but it still makes a punch. Although the overall silhouette of the dress is simple, its side slits and the strappy surplice bodice are attention-grabbing.
For your shoes or sandals, always choose the ones with thin straps. They make your feet look sexy.
6. The Blue Floral Print Off-the-Shoulder Midi Dress
Some dresses have natural demure effect whether they´re dressed up with heels or down with flats. The off-the-shoulder style, side-slit and cascading skirt of this dress are what make it extremely feminine.
So whether you´re going to dine at a fine restaurant or just visit a park, you can wear this dress to a date with the right footwear.
Dresses for Night Dates
Evening and night dates often mean dining out. Outfits for a night out can include darker colors and prints.
The following dresses are styles to consider if the guy is taking you out for a fabulous dinner. Their common elements are dark colors and print, sexy yet elegant, and feminine yet formal silhouettes.
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7. The Plum Purple Striped Satin High-Low Midi Dress
I would suggest to wear this dress in red for daytime (see dress #4). But for a night date, it`s best in plum . Having just the right amount of cute details — fluttering short sleeves, ruched shoulders and tonal burnout stripes — is what makes this dress a definite head turner. Being a subtle head-turner is a bonus.
8. The Leopard Print Satin Maxi Wrap Dress
If done right, a leopard print dress can be a stunning choice for a date outfit. But it can easily look matronly if worn with the wrong jewelry or makeup. Worse, it can give you a sugar mama look if done wrong.
To keep it elegant, wear the leopard dress with very little jewelry and natural makeup (avoid those shiny, glossy makeup, metallic lipstick and shimmering highlights).
Go for black strap heels (or black ankle boots with pointed toes in winter), and temper the wild print with a white or black jacket. You can add bright color to the look through your bag. Pink and red look good with leopard print.
For more tips on styling wild prints, check out my article over at my style blog, How to Wear Animal Print.
9. The Burgundy High-Low Wrap Dress
This dress is super elegant. The drama is happening on top, although the glimpse of leg also steals the show. It´s perfect for a formal dinner date.
10. The Coral Red Ruffled Asymmetrical Bodycon Dress
This look is perfect for when you go out to see a movie or a concert. Add a cute white or a metallic nude jacket to cover your shoulders. You can also opt for a black tailored jacket if you want to keep things formal.
11. Washed Blue High-Low Dress
A dress that can quickly transition from day to night. Worn with flat gladiator sandals, you have a comfy and flowy day dress. But for a night date with your guy, swap the flats with strappy high heels and add a necklace that matches the dress. Add a fitting denim jacket if you need to cover your shoulders.
Note that flowy materials such as of this dress tend to cling to love handles and other areas that you may want to downplay. If you have some areas that you prefer to hide yet you still want to wear airy and flowy dresses, go for chiffon.
Remember, you only have seven seconds to make an impression. Spending some time to plan your date outfit is key in making sure that you´re going to make a solid, positive impression of who you are + you´re going to have fun.