What to Wear on Your First Sugar Date: The Only 3 Things You Need to Know

By Caitlin


My very first sugar date began like every other date I’ve had in my life: with me staring in frustration at my closet and bemoaning my lack of appropriate clothes to wear.

Except this time, I didn’t even know what “appropriate clothes to wear” meant. Was I supposed to dress up in designer clothes and Louboutins like the sugar babies portrayed in the media?

I thought so. But one problem: I didn’t have that stuff.

So I ended up going out in what I can only refer to as “sassy-fied interview clothes.” Yes, I wore a dress shirt. And a formal skirt. To keep it from looking too secretary-like, I wore a pair of fantastic suede high heel boots.

The potential sugar daddy seemed to like it. Or at least he liked me. That first date led to my first arrangement.

Fast forward a few days later and I’m on my way to see this new sugar daddy of mine after a long day of classes. My hair is in a ponytail and I’m dressed down – way down – in a long cotton dress and sneakers. The only thing I had resembling makeup was some scented lotion I carry around in my purse. I slathered that on and rushed off to meet my sugar daddy, feeling terribly under-dressed.

To my surprise, my sugar daddy was delighted. He said his first thought when he saw me from afar was, “She’s super cute. I wish she was my sugar baby” followed by “Oh, sh*t. She is my sugar baby.”

He commented on how incredibly cute I looked the whole date. I was perplexed since the few times I’d met up with this sugar daddy, I’d been dressed up and thought I looked a lot cuter. But as it turned out, he was more into the super casual, girl-next-door look than anything else. He admitted that whereas I looked gorgeous when dressed up, I came off a lot more endearing and approachable when dressed down.

And just like that, I both knew what style of dress to wear on every single date with this particular sugar daddy and how to ensure myself unlimited access to shopping trips for clothing of the same variety.

Since then, I’ve went on many more first sugar dates and had the chance to meet a variety of sugar daddies, all with a vast range of preferences and tastes. And what I’ve found is that every sugar daddy has a style he loves on a woman, a look that he finds simply irresistible.

So how do you know what to wear on your first sugar date to make the best impression? It really comes down to finding the sweet spot between 3 things:

1. Your sugar daddy’s dress style

2. What you actually feel comfortable in

3. The venue

Let’s go over each one in more detail, shall we?

Your SD’s Dress Style

Chances are, your sugar daddy has a certain dress style. He might be a jeans and t-shirt kind of guy. In which case – he’ll probably love the girl next door look. He might be a sporty kind of guy. In which case – he’ll probably dig the sporty look.

But it’s just the first date and you obviously haven’t seen your sugar daddy’s wardrobe so how do you go about determining his dress style? Well, it’s not as difficult as it sounds. You can learn a lot about how a man prefers to dress and what style he feels most comfortable in simply by considering his lifestyle and personality.

His profession is one clue. If he works in a “suits” profession like banking and finance or corporate law, a casual chic outfit for you may be the most complementary. But pay close attention for insights into his preferences and what he aspires toward – for example, if he’s a “suit” with a creative side he doesn’t get enough time to explore, he’s going to be more intrigued by a sugar baby with an artsy, edgy look than the typical business casual ladies he sees everyday.

I’ve also gone on sugar dates with high-powered executives who were “suits” to their core as well as high-powered executives who were dying to strip off their suit persona as soon as the day was done so try to suss out what sort of “suit” they are prior to the date so you can appeal to what they’re actually seeking.

Another thing to consider is his personality. Look for clues on what he likes most about himself and how he wants the world to see him. Is it sophistication that gets him going? Innocence? Over-the-top trendiness? You can usually gauge what qualities a sugar daddy finds to be a turn on and a turn off through his profile and a phone conversation. Consider this as you choose your first date outfit.

Your Own Dress Style

Okay, now that you have an idea of what the SD may like, it’s time to consider what range of outfits you feel comfortable in. This is important not just for the first date but it can even be important in determining whether you’re a good fit for each other.

For example, I remember one sugar daddy who came off like a real snob in his profile so I took a little time to tease him about it prior to the first date to get more insight into what he liked. I discovered real quickly that he found the mainstream trendy shops like TopShop completely distasteful and could not fathom sugar babies who showed up to dates in sneakers.

In our conversations, it came across that he was the sort of man who would notice if that the shade of your eyeliner didn’t exactly your blouse or would judge you for having missed a wax appointment. Knowing myself, I knew this level of high maintenance would stress me out so I passed on this POT.

So keep in mind that one of the reasons you’re bothering to suss out his tastes and preferences is to determine whether you and your own tastes and preferences are aligned with the potential sugar daddies.

The Venue

The last thing you’ll definitely want to to consider is the venue. Especially since the first sugar date can be so many different things. If you’re going hyper-casual and meeting for a dog walk through the park, you obviously don’t want to show up in sparkly heels.

On the other end of the spectrum, if he’s flying you out for a weekend in Vegas and you’re usually a dressed-down sort of girl – you’ll still want to pack some heels and going out outfits.

If you’re meeting for an event that you don’t have much experience with – a fundraising dinner, a Moroccan restaurant – it’s helpful to ask friends who’ve been to similar events for tips or to simply Google image pictures to get a sense for what clothes are most likely to fit in.

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(1) comment

Zm June 13, 2018

Where should i suggest our first date be?!

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