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How sugar babies get ready to go on a date

Four sugar babies discuss style in the sugar bowl and how clothes can help you get the most out of your arrangement

There are two life events where people are often at a loss for what to wear: job interviews and first dates. For sugar babies, the stress is even more real, given the two events are combined, and a successful first date could well lead to a steady monthly income. 

Although sugar dating – where one person receives cash, gifts, or other material benefits from another in exchange for an intimate relationship – is in no way a new thing, controversial sugar baby and sugar daddy dating site Seeking Arrangement, and others like it, helped to propel the idea to the masses. Seeking Arrangement is not without its controversy, not least because its founder, Brandon Wade, once said that love is a fairytale for poor people. Despite that, the site boasts over 500,000 members from UK universities alone, with the average SA sugar baby income sitting at more than £2,000 per month. 

Sugaring has well and truly hit the mainstream – can we blame it on listening to too much Lana Del Rey growing up? It’s hard to say – but what is clear is that the existing stereotypes surrounding sugar babies still persist. The image of the Barbie-esque young woman in a tight minidress sitting on the deathbed of an octogenarian billionaire is still largely relied upon when it comes to interpretations in popular culture, and, thanks to Twitter, there are thousands of memes which depict what we’d likely wear for the very specific occasion of our old, rich husband’s funeral. In fact, in 2019, the reality is quite different.  

Jade Seashell is a former sugar baby turned luxury dating consultant and regular contributor to sugar dating advice site Let’s Talk Sugar, which, alongside Seeking Arrangement’s own blog series, is a popular go-to for budding babies, with how to dress for your daddy a huge topic across both platforms (one video on SA is literally entitled Dressing For Daddy).  

Based on her ongoing research, Seashell believes that there is a formula for dressing to get the most out of your sugar daddy. But, surprisingly, it’s not about dressing for men. “It’s about dressing so that the men will want to please women. The principles that I have written about regarding what to wear come from research on what most rich men respond to,” she explains. Having found herself a celebrity sugar daddy early in her career as a sugar baby, her style was extremely feminine and elegant, “so I didn’t change anything.” She advises that “the best outfit to wear on a sugar date is a beige dress, high heels, a pink bag and a pearl necklace.”

While they might get results among the sugar baby community, Seashell’s ideas are sometimes pretty controversial. She tells women not to cut their hair too short and to ‘walk like a lady’, with her advice often limiting women to reductive feminine stereotypes. That said, for many babies, playing up their femininity when on the lookout for a potential daddy is fun. 

“There’s a sense of superiority in dressing in a grossly sexy outfit and knowing the dumb old man will eat it up,” says 21 year-old sugar baby Sunday. “My sugar baby style is much, much more feminine and more ‘asset enhancing’ than my everyday personal style. One time I went all out and wore a mini skirt, fishnets, a bodysuit, heels, and a trench. I felt super mysterious in a really cliché, fun, seductive way.” But, she adds, “it’s a fine line because you want to look hot and worth the money, but you also want the waiters to think you’re having dinner with your dad and not a daddy.”

That’s not to say she’s not had any less-than-enjoyable experiences, though, with a number of daddies asking her to wear things she’s not been comfortable with.  “One time a sugar daddy tried to get me to wear nothing but lingerie and a trench in October, but I said no to that because I wanted money, not hypothermia,” she explains.

“There’s a sense of superiority in dressing in a grossly sexy outfit and knowing the dumb old man will eat it up” – Sunday

Sugar baby Clover Pittilla, 23, has been taken on shopping sprees and gifted designer jewellery, coats and shoes. But these gifts have a catch. If a sugar daddy is spending thousands of pounds on her at a time, he gets to pick the clothes that he wants to see her wear, which aren’t always what Clover would choose. For Clover, this isn’t necessarily a bad thing. “It’s nice to have someone else make decisions for you rather than having to decide for yourself,” she says. “I’m quite open-minded when a sugar daddy tells me what to wear. Everyone has a different sense of style and I like exploring what someone else likes.”

Clover once dated a daddy in his 70s who was very generous but the clothes that he picked out were old fashioned. “I was surprised to see them on me, but some of them actually looked really nice,” she says. “He’d had lots of experience with women’s fashion. He still had some clothes in his house that he’d bought for other women that he offered to me.”

For her first ever sugar date, Clover dressed casually in boots and jeans. “I was quite young so wanted to keep it simple,” she says. Having learned that dressing simply doesn’t fly, when she goes on sugar dates today, Clover always wears jewellery. “I never used to wear jewellery ever. I was afraid of losing it. When I go on sugar date, I feel more put together if I’ve got jewellery on. I feel more glamorous.” 

Of course, it’s not just women on the lookout for sugar daddies. John Aron started sugaring at 18 and immediately recognised the ways in which he could use clothes to his advantage. While his style was initially understated, he invested in an expensive watch to ensure he would fit into the world his sugar daddies would introduce him to very early on.  

Since then, he has edited his personal style to include luxury labels that wealthy men will notice. “When it comes to styling myself,” he says, “I realised that wearing something more expensive matters. I started wearing more luxury clothes, not because I could afford them but because when potential sugar daddies see quality, they respect you more and want to talk to you.”

His approach worked. When he went on a luxurious New Year’s cruise, his sugar daddy bought him an equally fabulous new wardrobe to match. “He bought me loads of Gucci clothes, as well as outfits from brands that I couldn’t even pronounce,” he says. “I was shook. It was incredible.” Now, he wears more ‘appealing, tight-fitting clothes’ than he previously did in an effort to show off his physique, and buys mostly high-end pieces to even out the power dynamic in his sugar relationships. 

“I started wearing more luxury clothes, not because I could afford them but because when potential sugar daddies see quality, they respect you more and want to talk to you” – John Aron

How you present yourself seems important when you want to show someone that you are worth spending money on, so it makes sense that sugar babies make alterations to their regular look. Being taken on dates to high-class restaurants and bars when dining with daddy also tends requires a certain dress code. Jade Seashell might suggest there is a formula to dressing for sugar dates, but in reality, they are a chance to experiment and change up your style, with much more creativity going into looks than these sugar babies might be given credit for. 

As with most scenarios in life, the most important thing is comfort, being genuine, and knowing your boundaries, both when it comes to style and how far you’re willing to go: so, not so different from the tips dished out when it comes to ‘regular’ dates. But if you want to play up to the clichés from time to time, that can be fun too. As Clover concludes: “It’s all about dressing comfortably, but still flashy. The more glitter, the better.”