Tone Down the Boobage and Other Valuable First Date Fashion Advice from Real Men

First dates can be nerve-wracking. Should you dress sexy? Should you not dress sexy? Are you showing too much? Are you not showing enough? There’s all these questions running through your head, and in the meantime, you have no freaking CLUE what to wear. That’s why we decided to go straight to the guys (you know, the dudes you’re trying to impress on that first date) to get the answer. We’re not going to lie, they give pretty great advice…

Jarrod Levine: General Manager of Whiskey Park Atlanta

  1. Wear heels, ideally stilettos – even if you’ll be taller than your date as a result!
  2. Keep it classy. Don’t pair a low cut top with a super short hemline – pick one. Personally, I’m a big fan of pencil skirts.
  3. Show off your personal style. If you’re into vintage, rock vintage.
  4. Don’t wear too much makeup or your date will wonder what you’re hiding underneath.
  5. Play up your favorite features – there isn’t a man I know that can resist a girl with bright eyes and sultry lips.

Sam Russell: TV & Red Carpet Wardrobe Stylist

  1. Men are already sooooo visual; leave a little something to the imagination. Now I don't mean you shouldn’t have ANY sex appeal; I would just show a little more leg and less boob starting out the gate.
  2. Make him remember your smell, and leave him with that. Your favorite oil or perhaps a magical perfume (Angel by Thierry Mugler) leaves an impression of chocolate and something sweet.
  3. Remember: how you dress for brunch with the girls is the opposite of how you dress for a first date…go easy on the accessories is my point. All that banging around and clunky costume jewelry is fun to talk about over Mimosas with your friends but not so much with men. 
  4. High heels are a must. Men looove a sexy heel! Avoid all of your designer labels at first though. It may come across as princessy or as someone out for a sugar daddy. As far as handbags go, ease him into your Gucci collection that maxed out your credit cards and drove your parents mad when you asked for a new one for five holidays in a row.
  5. No Hello Kitty…at all!

Kenny Kadar: Managing Director at Coast Medical Service

  1. Most likely the guy will be taking you to dinner, maybe even a movie. If it's something more creative than that, he’ll probably drop some hints. So dress accordingly.
  2. The best advice I can give you is to be yourself. Let your style shine. There’s no sense in hiding who you are (or what your style is like), just because it's a first date. Definitely don't dress in a way that is unusual for you, as the guy will eventually find out and be confused as to why you didn't dress like that from the start.
  3. Wear something that you can get away with in numerous environments; you shouldn't go too fancy or too casual.
  4. Do your hair and makeup, but don't get too crazy with it. 
  5. More important than the clothes you wear is how you wear them. Be confident in your own skin and make sure the guy knows it. Men love that…

David Bakke: Editor at

  1. The first thing I’d suggest is for the man and woman to discuss the topic. I’m not saying to discuss exact outfits, but if each party has a general idea of the expected dress, the first date will go much better. I can’t tell you how many times I’ve dressed casually for a first date only to have the woman show up in a skirt and heels.
  2. Next, and I’m not quite sure how to say this, but accentuate what you’ve got and hide what you don’t. If you have particularly attractive legs, an outfit highlighting that is great (you can figure out the rest of your look from there.) It's all about first impressions!
  3. Wear makeup and jewelry in moderation, unless it’s a high-class affair you’re attending. Guys want to see what you actually look like, not someone who’s buried under a load of cosmetics and earrings, necklaces, and bracelets. Keep the perfume at a provocative but modest level—guys have a tendency of choking on that stuff if too much is worn.
  4. Men tend not to keep up with women’s fashion. Therefore, your best bet is to go with colors and styles that are tried and true. I’m not saying to be boring about it, but using a first date as a way to try out the latest trends in women’s clothing may not be the best etiquette to go by. You can save that stuff for later dates.
  5. Lastly, don't break your budget looking for designer clothes; there are plenty of ways to get quality women's fashion at a discount, and most guys won't know the difference.