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The Perfect Sugar Baby First Date Outfit: Here’s What to Wear

Choosing the perfect sugar baby first date outfit is crucial. After all, first impressions really matter. Especially when it comes to the first sugar date.

Any potential sugar daddy might have been on dozens of dates with young, attractive women before he meets you. So it’s crucial that you bring your A game.

You want to take full advantage of that first sugar date to immediately make yourself stand heads and shoulders above the competition. And the most basic way to do that is by how you present yourself.

Yup, we’re talking about that ideal sugar baby first date outfit.

But how do you go about doing that? It can be tricky because there is no set outfit that works for all of us. The best sugar baby first date outfit is going to be different for each of us.

Here’s what you need to know to choose the perfect outfit for you.

What to Wear on the First Date with a Sugar Daddy

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.

What’s the Perfect Sugar Baby First Date Outfit?

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.

It’s Probably Not What You Think

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.

How to Choose a Sugar Baby First Date Outfit

Since that first date, I’ve went on many more first sugar daddy 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 Sugar Daddy’s 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 athleisure 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.

Here are a few tips.

  • 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 to aspirations. Look for some insights into a potential sugar daddy’s 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.
  • Look underneath the suit. 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? A wholesome youthfulness? 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 all of the above as you choose your first date outfit.

Your Own Dress Style

Okay, now that you have an idea of what the potential sugar daddy 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 naturally, 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 match 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 potential sugar daddy.

On the other hand, for a more polished sugar baby who despises fast fashion and has her wardrobe organized by cashmeres and merinos, they might’ve made a perfect duo.

In essence, 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 First Date 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.

Or you can simply check out some of our first date sugar baby looks for inspiration.

15 Perfect First Date Sugar Baby Looks

A great sugar daddy first date can be anywhere, from a casual neighborhood bistro to an upscale restaurant. Wherever it is, you want to look polished, put together, and gorgeous.

All without spending much money. The best way to do this is to use what you already have. Or to purchase some sugar baby essentials that are easy to mix and match again and again.

When I first started sugaring, my allowances weren’t as high as they are now so I learned how to stretch my money pretty quickly. After a couple of dates feeling a tad underdressed and just not great about how I looked in general, I decided I needed an upgrade.

The best advice I can give you when you’re starting out is that you need to pick some staple pieces – clothes you can mix and match and wear several times without it actually looking like you’re recycling it.

Here are some perfect first date sugar baby looks with staple wardrobe items most of us already have in our closets or can easily buy.

The Little Black Dress

Most of us have a little black dress. It’s a classic wardrobe staple for good reason. And it’s also a perfect piece to wear for a first date with a sugar daddy.

But not any little black dress will do. The one rule is that this dress should be a showstopper. Something you feel super confident in and definitely something that emphasizes your best assets.

At the same time, it needs to be somewhat subtle in that it can’t show all your assets, if you know what I mean. Think thigh skimming, cleavage-plunging, or form fitting. Choose one, not all three.

The little black dress makes such a good first date outfit. You can dress it up or down depending on what the venue is. More casual bistro or restaurant? Do the LBD with sneakers. A museum date? Keep it looking cute with ankle boots. A fancier dinner date? Rock the heels.

It can be sexy, cute, elegant, sophisticated. Whatever you want. So much versatility with such a little dress.

A Killer Dress

A killer dress is a definite staple I would recommend having if you’re in the sugar world. The ‘all black’ rule can well and truly be thrown out the window for this one!

Whatever the color is, if you have that one little go to dress – that could be the perfect first date sugar baby outfit.

As we all know, men are very visual. So if not black, I usually go for bold colors like red or blue. Bright colors that grab attention and really show off your figure are probably best. Although if you’re more comfortable in a more low key color, you can never go wrong with neutral tones.

If you’re wondering where to go for an affordable option – on the low end, check out websites like Missguided, Asos and Pretty Little Things. If you can spend a little more, Aritzia, Anthropologie, and & Other Stories are great places to look. They have large selections and again, there’s something to fit every body shape. There’s also constant new stock coming in so be sure to check out the ‘sale’ sections.

Pair of Blue Jeans

A really great pair of blue jeans should be a staple in any girl’s wardrobe so you probably already have a go to pair. If you don’t yet have a flattering pair, get some. Because you will definitely need them entering into the sugar world.

A lot of dates you go on will be in restaurants. But there will also be times when you’re going on more casual dates, like the movies or my favorite – shopping trips!

You can pick anything from low slung to high waisted, zips, buttons, even lacy detailing on some pairs. You can dress them up with your killer black heels. Or throw on a pair of sandals or trainers for a more casual look.

Black Jeans or Trousers

Most of us have at least one pair of black pants that fit and look great. They’re a must have for a reason – they are somehow way classier than jeans or leggings and they’re super flattering on any shape.

If jeans aren’t your thing, I’d highly recommend cigarette pants although feel free to find a style to fit your body type. You can get inexpensive pairs on websites like Asos and Missguided that definitely don’t look cheap.

You can dress them up with a cute blouse or a fitted jumper. They’re also easy to dress down with a cute tank! Either way you’ll look sophisticated and sexy.

A Black Skirt

I know, I know – black again. But most of us tend to have a black skirt in our wardrobes so it’s a good place to start.

If you don’t yet have a black skirt – get one. They are always the best buys at first. They’re so easy to pair up without actually looking like you’re repeating your outfits over and over again! A plain black skirt will also only set you back around fifteen to twenty dollars and can be picked up from stores like Forever 21 or H&M.

My current staple is a stunning black suede mini skirt. It was a gift from my sugar daddy during a shopping trip in Texas. Again, a skirt like this can be dressed up in no time. Think a tight black tank and strappy black heels for dinner dates. However, it’s always easy to dress down- throw on a pair of cute sandals for daytime lunch dates.

Bonus: Black Strappy Heels

This might be an obvious one. But if you don’t already have a killer pair of black heels, now is the time to invest. I’d recommend a pair of strappy, barely there heels. I got my first pair from Public Desire for less than $40. They’re a dead ringer for a YSL pair more than ten times the price! They go with absolutely everything and who doesn’t feel ten times sexier in a pair of great heels.

Editor’s Tip: If you’d prefer to have a pair of couture heels to start your sugar journey in but don’t have the funds – try The Real Real. It’s an online consignment shop with a huge array of couture shoes that are in great condition and clean. You should be able to scoop up a pair of beauties for, like $100.

More Tips for the Sugar Baby First Date Outfit

Still not sure what to wear? Here are a couple more tips to get you there.

Ask him

One of the best sugar daddy questions to ask pre-date is what sort of women he likes. What does the ideal woman look like?

That gives you an idea of what you can wear to impress him. If his emphasis is on natural, the Girl Next Door aesthetic works well. If he uses words like sexy and hot, go for Casual Chic or Understated Sexy.

Read: Sugar Baby Outfits: What to Wear & Not to Wear

You can find examples of all the looks we describe by checking out the above article.

Let him decide

If you’re feeling daring, feel free to simply ask your sugar daddy what he wants you to wear. This will be especially sexy if he’s a dominant type and you’re a submissive.

Be Comfortable

You need to feel comfortable in what you’re wearing in order to feel confident. And at the end of the day, the most beautiful girls are the most confident ones.

So find some really great pieces that complement your body. You’ll be looking and feeling like a rockstar in no time!

Subtle and Classy Wins

When in doubt, always err on the side of subtle. Of course, you want to dress for the occasion but at the end of the day, classy always wins.

Sugar daddies tend to be older, classier, refined men. They want someone who’ll mesh with them and not make them feel even older. Remember this as you dress for the first sugar date.

All in Good Time

Most of us start our sugar baby journey without much spending money to shop with. But as you get more experienced sugaring, your allowances get higher. Plus, you’ll go on shopping trips with the sugar daddies you’re seeing.

It’s almost guaranteed that your wardrobe will improve. All in good time.

And there you have it. Armed with these sugar baby first date outfit ideas, you really can’t go wrong. Now go out there and impress his socks off.

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