How To Dress For A Date

By Alexis G

Apr 13, 2016

Not sure how to dress for a date? Don’t panic, the guidelines below will teach you how to look flawless for any occasion.

Know Your Venue

If you are not familiar with the place Daddy is taking you, do a little research. Many restaurants include information about the dress code online. If you are headed to an event such as a wine tasting or a cocktail party the same rule applies. Research where the event is taking place and what time of day the event is being held. This will help you decide what kind of attire is appropriate for the occasion and make Daddy proud to have you at his side. This is also a great time to look over the menu and be prepared so you’re not staring aimlessly for 20 minutes.

Don’t Over Do It

Anyone can show up wearing a form-fitting, cleavage-revealing outfit. Dare to be different and mix it up a bit. Choose ONE body part to show off. If you have legs for days wear a short skirt, but keep your top modest. If squats are your best friend show off that derriere in something form fitting, but avoid showing too much skin. Is your cleavage too amazing to keep to yourself? Wear something low-cut, but keep it classy on the bottom. Remember if you got it, flaunt it – just not all at the same time.

Comfort Is Key

No, I’m not talking about wearing sweatpants. Wear clothing that makes you feel confident and comfortable. Try on your complete look the day before the date. Walk around, sit on different chairs and couches and snap a couple of photos to check out the entire outfit. This will allow you to see how comfortable you feel in the outfit, if you have to adjust your clothing every time you sit down or stand up you should probably consider changing it up. Don’t forget: a date is not the time to break in a new pair of heels.

High Heels, High Hopes

It’s no secret that most men love to see a woman in heels, so take that into consideration when planning  your outfit. Heels of some kind are appropriate in nearly every date situation. If you have trouble walking in heels be sure to practice. Do not feel pressured to wear 6-inch pumps, experiment with different heights and heel types until you find what works for you.


Makeup should be used to enhance your natural beauty. For a casual date keep your makeup light and fresh. For a night on the town feel free to add a little drama with a bold lip and a smokey eye. Use foundation and concealer to hide imperfections in your skin, but don’t apply so much that your skin looks like a mask. Pro tip – Invest in lip stains in various shades. This will remove the need to reapply lipstick throughout the date and help you avoid embarrassing lipstick stains on your teeth.

Now that you know how to dress for your next Sugar date it’s time to get out there and strut your stuff.