In the world of sugar dating, where first impressions matter a great deal, dressing well is essential. Wearing the right clothes is more than just fabric and fashion – it reflects your confidence, personality, and silent intentions. 

Whether it’s a casual coffee date or an elegant dinner, what you wear can set the right tone. Emily has been a sugar baby for 3 years, has had 5 long-term sugar daddies, and has been on countless sugar dates, so she’s figured out what makes sugar daddies tick when finding the right outfit for sugar dates. 


Flaunt Your Style

Flaunt your sugar dating style

Q: What’s your first advice when choosing an outfit for a sugar date?

Emily: “My main advice is to show your style. Your outfit reflects who you are, so not only are you flaunting that, but since it’s your style, you will feel comfortable in whatever you wear. If you love dressing up or immersing yourself in colors, go for it! If you’re more of a casual kinda person, don’t force yourself into a suit. Authenticity is attractive, and showing your true self through clothing can create an instant connection with the right person.” 


Dress For The Occasion

Dress For The Occasion

Q: Can you share tips on dressing for different types of dates?

Emily: “Dressing for the occasion is all about being prepared. Before going on the date, research the venue and plan accordingly. The last thing you want is to show up for a walk in the park in your highest stilettos! It will be a good look – if you can walk comfortably for hours in 4-inch heels. 

For casual coffee dates or walks, choose well-fitting bottoms that accentuate your curves and a stylish top to match. Comfortable footwear can help the conversation flow more freely. Consider a smart-casual outfit like a lovely dress or a tailored blazer and trousers to make a strong impression if it’s a formal setting.”


Accessorize Smartly

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Q: Over or under-accessorize?

Emily: “Good question! Accessories can elevate your look, but I advise that less is more. Opt for one statement pieces like a watch, a delicate necklace, or a stylish belt. Accessories are another way to express your personality without overpowering the whole look, so don’t be afraid to flaunt your favorite pieces (one at a time).” 


Find A Balance Between Casual & Chic

Find A Balance Between Casual & Chic

Q: How do you strike a balance between casual and chic?

Emily: “Mixing casual and chic can look like pairing a well-fitted blazer with jeans and sneakers – a classic go-to outfit for stylish Parisians. Ultimately, it’s about combining elements that seem to go against each other in theory but look harmonious and stylish when combined.” 


Confidence Through Clothing

Confidence Through Clothing

Q: Going on dates can be pretty daunting. Do you have any tips on dressing to boost one’s confidence?


“Clothing IS a powerful tool for boosting confidence. When you feel good in what you’re wearing, it reflects in your demeanor, so wear clothes that make you stand tall and feel comfortable. It’ll show if you’re uncomfortable in tight clothing or sky-high heels. Confidence is about feeling at ease in your skin; your outfit can support that. Nevertheless, this can look different for everyone as we have different tastes and styles, so find something that suits you.”


Playful And Flirty Touches

Playful And Flirty Touches

Q: Could you share tips on adding playful and flirty touches?

Emily: “I personally love wearing pieces that accentuate my natural curves to create a flattering silhouette. This in itself gives off a flirty, sexy vibe, and it makes me feel sexy too. Other ways you can do this if tight clothing isn’t your thing is to add a pop of color (such as seductive red tones), a stylish accessory, or even something as simple as a bold red lip.”


Outfit Ideas For Different Dates

Outfit Ideas For Different Dates

Q: Any inspiration for our readers on different outfit ideas for different dates?

Emily: “From my experience, most sugar dates tend to be somewhere fancy, like a nice bar for drinks or a classy restaurant for dinner. For dates like these, the classic little black dress and heels are always a winner, trust me! I have many dresses on rotation that make me feel confident and comfortable. 

Sometimes, it’s more casual, and you can still stick with the little black dress; just match it with comfy (yet stylish) sneakers or sandals. During hotter days, I love wearing sundresses for outdoor activities. As for casual dates indoors, like a coffee date, you can’t go wrong with jeans, a nice blouse, and sneakers for footwear.” 


Grooming And Hygiene Matters

this is a problem i havent faced before GIF

Q: How important is grooming and hygiene?

Emily: “Your finished look will only look as polished with grooming and hygiene. No matter how on-point your outfit is, if you ignore getting your hair in place, it can look like you just rolled out of bed, sending the wrong impression. 

Like most girls, I have monthly maintenance services like waxing appointments, mani-pedis, brow, and lash services, and you name it. All these help make my life easier as I don’t need to do much, like shaving or cutting my nails before every date. Also, don’t forget to brush your teeth!”


Comfort And Confidence

Comfort And Confidence

Q: How do you strike a balance between comfort and confidence?


“Comfort and confidence go hand in hand. If you wear something that feels good on your skin, shoes that you can walk comfortably in, and your overall outfit fits you well, you will feel more comfortable, making it easier to exude confidence. In fact, you don’t even need to try. But if you’re constantly adjusting your outfit or feel uncomfortable, it can cause you to lose focus and hinder your confidence.”

Q: Thank you so much for your chat today. Any last words for our readers on what to wear on sugar dates?

Emily: “I know everyone says this, but the key is to be yourself and have fun! Your outfit should complement your personality and make you feel fantastic. This way, your true, amazing self shines through and makes a killer impression.”

In a nutshell, the perfect date outfit isn’t just about looking good. It’s about expressing your personality, feeling confident, and, most importantly, creating a connection with your sugar date. 


Got an outfit that you’re excited to show off? Plan your next date on Sugarbook today!

We also have plenty of other sugar dating tips and advice. If you’d like to learn more, check them out here:

Top 10 Questions to Ask Your Potential Sugar Daddy or Sugar Baby

How To Ask A Guy Out Over Text In 2023 (Tips & Tricks That Help You)