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Dating & Mating: How to dress on a first date

I'll let you in on a secret: I'm single. Yes, I know what you're thinking. "Not you Bree! How is this possible?!" I too have these same thoughts, lol. Regardless of the reasons, I have my freedom papers and am enjoying my new found singlehood, which includes many dates. Tempering that excitement is the anxiety of trying to figure out what to wear on a first date. So, I've decided to share my in-depth research and interesting findings.  After reading popular magazines, asking women and girlfriends... I then chucked that info. I figured I'd ask who mattered most- the types of men I wanted to date. Gathered men! So I'll share my findings about what creates the best impressions in gathered men's minds regarding first dates. Here are some general rules to follow:

  • Don't dress for women, i.e. Super trendy, intimidating fashion (heel-less shoes, channeling your inner beyonce/lady gaga diva outfits). A good rule of thumb is: imagine or ask your girlfriend's reaction to your outfit when she first sees you. If she screams "Fierce! Work! Beat! Diva! or any other Zoolander terms- it's too much for a date. Good words are "super cute, pretty, beautiful, lovely, good/great, even "hot" is okay.
  • Less is more: make-up should be simple and not complicated (no rainbow eye shadow). focus on one facial feature to enhance (lips- vs- eyes). You don't want red lips and dark smoky Cleopatra eyes.
  • Grooming is everything. There's a reason Outkast made a whole song about being "So fresh and So Clean". Remember the small details: neat manicure and pedicure, arched eyebrows, moisturized skin, clean hair. Basic stuff. (also see Back to Basics Pt. 1 and 1.5)
  • Take the sex appeal between a 6 and 7 on the sexy scale. A Zero would be a muu muu or shapeless jogging suit. A 10 would be a heavy cleavage, leg and thighs exposed, and form fitting to your hips and butt, thus showing all your lady lumps. You want intrigue and suggestion, not a huge red light district sign.
  • Aim to show 40 percent of your body. Studies show this yields the most male reaction and attention. Again, the point is suggestion. A first date outfit is like a movie trailer. How, you ask? Well, everyone hates when a movie trailer shows too many action scenes or funny jokes. It makes the movie lose it's luster and you wonder if the movie has any substance beyond all the flashy spoilers. A man will still  try to see the movie, but he may wait for redbox instead of choosing the box office opening weekend $14 ticket. You are worth opening night behavior!
  • Stay prepared (See 7 items for your clutch). Bring a jacket of some sort. You won't ever regret it. And if it's too hot, he can hold it for you. That's what gathered gentleman do.


Keep in mind that these are first date options, which are about impressions and set how he unconsciously thinks and behaves with you. Once you snag him as your exclusive man or husband, then you can go crazy and walk around in your muu muu or head to toe animal print catsuits! Just kidding, stay calm and dress gathered. Here are some examples of good date outfits:

Date Option 1:  Lunch date, Movie date, Casual Date

This look is perfect for dating in your 20's. Generally the tone of the date is casual, won't include active movement or sports, and may not cost big bucks. This look conveys femininity without pretentiousness. The dress can be in any color, and is flattering on most body types. The shoes have sex appeal without the intimidation or discomfort of a full on high heel. The purse can be easily carried  across the body if you take a scenic walk.

Date Option 2: Live music concert, Art walk or show 

 This look screams "I'm cool." Which you obviously are. The top is a sexy combination of leather and exposed decolletage. The jeans balance the top, but shows peeps of leg. The shrug is sheer. The suggestion factor is high on this outfit. The shoe is great for walking or standing long periods of time (thick heel, less than 3 inches, toes covered in case of concert misstep). 

Date option 3: Park Picnic, Flea Market, Beach, Outdoor activity

 Have I mentioned my love of rompers and playsuits? If I haven't let me shout if from the rooftops! They can be extremely versatile and stylish. They eliminate having to match pieces. The cuteness of a dress, with the flexibility of shorts. Le awesome. Men find these appealing because they have a youthful charm and show lots of leg. Make sure it's a good fit (not too tight or baggy) in order to keep the sexy in target zone. I paired this with a natural make-up like NARS orgasm blush and simple accessories. 

Date Option 4: Cocktail event, Fancy dinner date, Theatre

 These dresses are prime examples of the 40% law of attractiveness. Shoulder action combined with some leg display is ideal. I've tested this theory out many times, it works. Opting for a body conscious fit pushes it higher on the sex appeal scale, so covering cleavage is important. The middle look is a an awesome plus size choice. Make sure you use proper supportive undergarments to make these look flawless. Simple jewelry, strappy heels, and signature clutches make these looks chic and sexy. 

Do you have a first date that doesn't fit into these categories? Need help? Write us at and we'll help you figure out great styling for a first date. Do you have pictures of your first date outfit that rocks? Email or tag us on facebook, twitter, or instagram @Thegatheredlady and if we like it, we'll share it!

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