Classy or Trashy? Looking Good for your First Date

Special thanks to SB Ashley  for suggesting this post. 

You’ve seen a fabulous dress that’s in your size, in a gorgeous color, and on sale. In fact, you’ve seen this in a magazine before, and you remember how great it looked on the  5’7 woman with long brown hair.  You decide to try it on and look at yourself in the mirror.  

It doesn’t look so great on you. 

Although the purple looked good on her, you start to feel that purple on a short bleach blond haired and pale skinned girl looks pretty dull.  

Instead, you go for the LBD (little black dress) that you saw her wearing.  You try it on, and it fits and looks great on you!  However, you remembered in the picture of the brown haired girl, she wore no accessories. Her hourglass curves made up for all of it.  Your pencil shaped body needs more though. You need to accessorize. 

It’s often times hard to say what will work for clothing, and what will not.  How an outfit looks can depend on anything from hair color to the size of your breasts.  But here I will try and guide you on some decent looks to shop for when meeting up with your pot, and more importantly affordable prices for the first time SB. As Ashley mentioned, a lot of girls end up looking extremely trashy instead of classy. Maybe they get nervous, or they’re not fashion inclined, but hopefully these tips will help future and current SB’s!

Do you know what to wear when you meet your SD?  I’ve compiled some “Choose this over that” dresses, shoes, accessories, hairstyles and make up for you.  After each dress I will list a cheaper alternative less than $50


Date Dress:  The dress on the left  should be chosen over the dress on the right. Here’s why:

The feathering detail on the bottom of the right dress makes it look very young and cheap, plus the emphasis goes right to the bottom. Unless you’re a small size, this dress would be hard to pull off (even for them).  However the dress on the left feels more mature and seductive. The emphasizes is focused on the midsection which makes your waist look smaller.

You can find a somewhat similar and much cheaper dress here.

Little Black Dress: The dress on the left should be chosen over the dress on the right. Here’s why:

The dress on the right seems very frumpy and “school teacher-ish.”  The belt is brown and boring, and makes her body look stiff.  It seems like something you’d wear at a funeral over a date. The dress on the left, however, has a gorgeous neckline.  It plunges at the back, which gives it more of a seductive feel.  This dress would be incredibly easy to accessorize and would look even better with a white shawl.

You can find a cheaper alternative here.

Evening Dress: The dress on the left should be chosen over the dress on the right. Here’s why:

The dress on the right reminds me of a cake.  The layering at the bottom is too much for such a long dress. However, the dress on the left is beautiful and elegant.  The off shoulder reveals a little, but not a lot, and in my opinion, keeps the SD wondering and attracted too you.  The ruffle at the side is gorgeous also. It adds a little detail, but not too much to overwhelm anybody looking at you.

You can find a similar and cheaper dress here.

Cocktail Dress: The dress on the left should be chosen over the dress on the right. Here’s why:
The dress on the right has sequins. Avoid sequins girls. They look tacky unless you’re a college party girl. The shirt looks so baggy that I can’t tell if she even has a chest or not.   The dress on the left is gorgeous, though. It flows well, has a great belt that, again, emphasizes the  waist. It looks sexy without feeling slutty, and the shoes look great with it.  Even though it has longer sleeves, it goes so well.
You can find a somewhat similar and much cheaper dress here.
Plus Sizes: The dress on the left should be chosen over the dress on the right. Here’s why:
Can’t forget my curvier ladies! The dress on the right should be avoided for plus size girls.  This dress has an insane pattern, which should be avoided. The lines are horizontal, which creates an illusion of you being wider than you actually are.  This woman, although gorgeous, looks larger than I believe she is because she has nothing to emphasize her curves. On the other hand, the dress on the left is a solid color, shows the waist, and makes her look smaller than the right girl.
You can find a similar and cheaper dress here.


The shoe on the left should be chosen over the shoe on the right. Here’s why:
For most girls, and most outfits, high heel boots look extremely tacky.  I’ve always viewed them as to be something worn on a corner or in bed. That’s not to say I never wear them, but it takes a special outfit to pull them off. The smart thing to do would be to choose regular heels.

Accessories Tip

Accessories should never be overdone.  Try and keep casual accessories for casual meetings.  When going on a date it is more appropriate to wear this simple necklace over this one. I recommend Harajuku Lovers: Love perfume. I’ve always had comments about my perfume on dates when wearing it!


Try not to overdo it with a hairstyle, but don’t do nothing, either.  There is a girl on youtube who does some gorgeous styles.


Make Up 

Make up is one of the most important things that will make you look hott, or not.  Glamour has some decent make up ideas, but it’s about choosing to pair what with what.  For example, number one: “Go for major lash drama.” I would use with the cocktail dress but not for the evening gown. You can also youtube make up tutorials and find some great ideas!

 You can check out my Polyvore account here for extra fashion advice and ideas!  I’ve never made an account there until now, and I love it!  


12 thoughts on “Classy or Trashy? Looking Good for your First Date

  1. Though I totally agree with your assessment of style in this article I have to say that sometimes trashy can be sexy. For example, there’s a lingerie boutique here in LA called Trashy Lingerie and they specialize in sexy, punk rock lingerie that has that classic trashy sexy look without being clichè. Also, some daddys want to harken back to their youth and this may involve going to crappy bars or clubs. An SB who could pull off a creative trashy look might be a great fit for an adventurous PR SD.

    • Good point. I think for the majority though, a lot of SD’s are more into a classy look. Plus, I don’t know many girls who would want to wear trashy lingerie on the first date 😮

  2. What if you have neither the nice clothes or the money to get anything nice.. Like im kinda stuck with jeans and a hoodie til I get my sugardaddy.. what do you think I should do?

  3. I know it’s probably too late for this comment to help Brooke, but…

    Check out thrift stores! KMart and Walmart have pretty things, if you take time to look for them… can’t worry about the brand until you get the SD! As a last resort, buy THE perfect outfit, leave the tags on, and return it for a full refund. As long as it’s not stained or stretched, it’s not unethical, right? 🙂

  4. What does one wear to meet up with potential sugar daddy at coffee shop? Do I wear casual wear? Or is there certain style I must apply?

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s