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The First Date Style Guide Every Woman Needs

When it comes to dressing for your first date, it’s important to choose an outfit that makes you feel confident and attractive. 

So, what’s the best way to dress for a first date? Well, that depends on the type of man you’re dating, and the type of lady you are. Some guys prefer a more casual look, while others are drawn to women who dress up a little more.

In this style guide, we’ll give you three looks that are always sure to impress, along with tips on how to style each look for your specific date.

Style #1
The Girl Next Door

Casual and Cool

There’s something about the girl next door style that just creates warm and fuzzy feelings in men’s hearts. It’s natural, effortless, and always looks good. If you’re looking to encourage a man to be more receptive and open to you on your next first date, this is the style for you.

What You’ll Need

  • Messy bun
    • With a sweet-looking hair tie or claw clip 
  • A light, airy blouse, or a crop top
  • Jeans 
  • Flats or Sandal Heels
  • Makeup Looks
    • Natural, No-makeup makeup
    • French Girl Look: Minimal makeup, but with a blotted red lip
Moodboard The Girl Next Door

You should wear this style if you…

  • Are comfortable in your own skin
  • Prefer to spend minimal time dressing up
  • Do not like ultra-feminine styles, and prefer something neutral

You should NOT wear this style if you…

  • Like to dress up and look absolutely perfect
  • Want to turn heads  
  • Have a colourful personality, and would suit more distinctive, specific styles. 

Style #2
The Sexy Siren

Power Red

Go for this look if you’re looking to feel sexy and powerful on your first date. This look is all about commanding attention. Men love this style because it exudes strength and femininity at the same time. It shows that you’re unapologetically yourself. What’s more, science has proven that red on women drives men wild.

What You’ll Need

  • A little black dress
    • Or any other dressy outfit that incorporates darker tones
  • Makeup Looks: 
    • Soft Glam
    • Pin-Up Look
    • MUST: A Red Lipstick that suits your skin tone 
  • Red nail polish that suits your skin tone
  • Heels

*If you’re unsure which red suits your skin tone, do consider consulting Store Assistants at makeup counters, trying on several before buying, or leaving all this work to a professional image coach who will guide you instead.

>>Click here to contact us in order to find out more about professional image styling to upgrade your look.

Moodboard The Sexy Siren

You should wear this style if you…

  • Love the idea of looking classically bold and feminine
  • Do not mind spending time perfecting your makeup and style
  • Are experienced in styling or have an image coach to guide you

You should NOT wear this style if you…

  • Tend to be shy or uncomfortable with attention 
  • Do not know your best shade of red
  • Have a more relaxed or casual style or personality

Style #3
The Glamorous Goddess

Feminine and Flirty

You can’t go wrong with a sundress when dressing for a first date. There are endless memes on how much men love sundresses. Sundresses are both functional and incredibly cute. They are the perfect in-between – not too casual and not too dressy. Men will always fawn over a woman in a sundress because they are a breath of fresh air. They’re flattering on every woman.

What You’ll Need

  • A sundress in a bright colour or floral pattern 
  • Natural hair worn down
    • Or soft waves 
  • Makeup Looks: 
    • Korean Popsicle lips 
    • Natural makeup with some shimmer
    • Optional: add a pop of colour with light/pastel coloured eyeshadows, or a vibrant coloured but soft eyeliner
  • Necklace and Earrings 
  • Wedges or sandals
Moodboard The Glamorous Goddess

You should wear this style if you…

  • Want to feel pretty and feminine 
  • Want to show off your curves
  • Would like to come across as warm and inviting

You should NOT wear this style if you…

  • Tend to be self-conscious about your hips or stomach
  • Are not comfortable in dresses
  • Have a more edgy style or vibe

Conclusion

When it comes to a first date, one of the most important things you can do is dress well. You should dress well not just for the other person, but more importantly, for yourself. You want to look your best, and feel your best. After all, you never know where things might lead.

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Interested in 1-1 Personal Image Styling Sessions or Workshops?

Interested in 1-1 styling advice for your own body type? Want a certified image stylist to bring you around shopping for your best clothes? Want to receive personalised, curated advice on how to dress to look your best? *Want to find out what’s YOUR best shade of red?

>>Click here to contact us in order to find out more about personal styling for yourself.

Psst! Don’t have a Date yet?

Perhaps you are simply too busy to meet new people. Or there just aren’t enough opportunities in your life to meet a potential lady whom you may click well with. At GaiGai, we match dates up according to compatibility and individual members’ criteria, which will aid in creating that spark you’re looking for.

>>Click here to sign up for a FREE profiling session to find out if there are profiles in our database that are compatible with yours.

Want to join a GaiGai Event?

We typically host 2 events per month.

>>Click here to check out our latest events.

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MEN’S OUTFIT STYLE GUIDE: THE TOP 3 LOOKS WOMEN LOVE

You’ve scored a date with the lovely lady you’ve been eyeing for weeks. Or, you’re eyeing a lady you’ve just met and now want to draw her attention to you. 

First impressions are everything. It takes just 7 seconds for someone to form a solid first impression of you. So…the pressure is on to make a good impression on the woman you’re eyeing. What should you wear?

You want to dress in a way that makes you feel confident and comfortable, while also impressing your date or crush. So what are the top 3 looks women love? We’ve got you covered.

Check out our simple style guide for men, and choose an outfit that will make you look and feel your best.

LOOK #1
THE CLASSIC GENTLEMAN

You’re a classic gentleman. You like to enjoy the finer things in life and aim for the best. You’re always well-dressed, and you know how to make a woman feel special.

This look is all about sophistication and a timeless style. When you walk into a room, you want people to take notice. You’re the man with presence.

What You’ll Need

  • A fitted suit in a dark colour, like black,  navy blue, dark grey or dark brown
  • A dress shirt in white, cream or light blue
  • Dress shoes

Women Love This Style Because…

  • You look polished and put-together
  • You have a sense of style that’s both classic and timeless
  • You’re the type of man who knows how to take care of himself…and take care of the woman he loves
Moodboard The Classic Gentleman first date style guide for men

Who should wear this style:

  • Men who want to put his best foot forward 
  • Those with a high achiever attitude 
  • Men who prefer traditional courting and romance
  • Men who can present themselves in a confident way, speak eloquently, with a charming or commanding presence.

Who should NOT wear this style:

  • Men who want to appear casual or trendy
  • Those who are attracted to the simpler things in life 
  • Men with a more relaxed style and looking for a partner who matches that laid back vibe 
  • Men who tend to feel nervous around ladies he likes

Look #2: The Modern Man

Let’s take a look at the modern man. This is a style that’s all about looking put together without trying too hard.

What You’ll Need

  • Well-fitting shirt
  • Jeans or trousers
  • (Optional) Plaid or Chequered shirt jacket – nothing too flashy

Women Love This Style Because…

  • It’s very clean and timeless. 
  • Shows that you’re realistically put together and have your life together. 
  • Suggests that you’re a balanced guy who puts in some effort in looking presentable, yet may be spending his time on other projects and hobbies.
Moodboard The Modern Man first date style guide for men

Who should wear this style:

  • Men who want to look stylish without too much effort 
  • Those who haven’t figured out their specific style 
  • Men who prefer simplicity, but still have to make a good impression 
  • Men on a budget, as such clothing can be found everywhere at varying prices

Who should NOT wear this style:

  • Men who have decided on a specific style should follow their own unique style instead
  • Men with a very interesting personality or background should dress less generic and incorporate elements (accessories) of who they are 
    • Ie men working in arts may choose to dress with prints or in a more flamboyant way
  • Men who prefer to look professional and polished

Look #3: The Creative Type

The creative type look is all about being yourself and expressing your personality. The possibilities are endless when it comes to styling for this type. 

What You’ll Need

  • A few items (2 or more) with an element of flashiness.
  • An item with an element of flashiness 
    • Shirt with prints 
    • Or Shirt in a bright or pastel colour 
    • Or Pants in a bright or pastel colour 
    • Accessories
      • Piercings 
      • Rings 
      • Necklace(s)
      • Wristbands or Watches 
    • A trendy haircut 
      • Shaved line 
      • Eyebrow cut 
      • Spikes + Slash
    • Trendy shoes to complete the look

Women Love This Style Because…

  • It’s creative and unique. 
  • It shows that you’re not afraid to stand out from the crowd. 
  • It suggests that you have developed your own identity and you are assured in yourself as an individual. In return, you would embrace and respect your woman’s individuality and sense of self.
Moodboard The Creative Type first date style guide for men

Who should wear this style:

  • Men who know they have a unique style, personality or skill
  • Those who are in the art, music, entertainment, or other alternative industries
  • Men who take pride in their individuality and want to stand out from the crowd
  • While this may sound counterintuitive, men who are shy, soft-spoken and tend to make themselves small may want to experiment with this style, as this may help such men come out of their shells. 

Who should NOT wear this style:

  • Men who are more traditional. A cleaner look would suit them better. 
  • Those who do not want to spend time on developing their style as specific styles tend to require some maintenance
  • Men whose values lean towards conformity rather than individualism
  • Men who find it cumbersome to wear only 1-2 accessories.

Conclusion

When planning your first date outfit, it’s important to dress in a way that makes you feel confident and comfortable. These three looks are all stylish and sure to make an impression on your date or crush.

So, don’t wait any longer – start planning your outfit today and wow her with your style and presentation.

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Psst! Don’t have a Date yet?

Perhaps you are simply too busy to meet new people. Or there just aren’t enough opportunities in your life to meet a potential lady whom you may click well with. At GaiGai, we match dates up according to compatibility and individual members’ criteria, which will aid in creating that spark you’re looking for.

>>Click here to sign up for a FREE profiling session to find out if there are profiles in our database that are compatible with yours.

Want to join a GaiGai Event?

We typically host 2 events per month.

>>Click here to check out our latest events.