ask sabatino- proper date attire

Dear Sabatino:

I am recently divorced and have been trying to talk to this woman at my job for months. She finally agreed to go out on a date with me.  I’ve decided to take her to a local Tapas Bar here in town, but it’s been a long time since I’ve been out on a date and I don’t know what I should wear.  I don’t want to be too dressy, but don’t want to look like a slob.  What would you recommend?



Hi Jared!

First dates and impressions are super important, so I’m glad you’re taking your attire in to serious consideration.  I think the first step is to consider the mood you’re trying to set.  If it’s cool and casual, then your clothes should present that and likewise if it’s romantic and formal.

Also, consider where your date is taking place, you don’t want to be overdressed for the location.  I love the idea of a tapas bar because you can order a few small dishes and split them, without looking like you’re eating a whole bunch, and usually they’re relaxed settings great for conversation. We have a local tapas bar here that I use frequently for first dates.  It’s a little classier than “jeans and t-shirt”, but not formal enough for a suit.  I usually show up with a nice pair of jeans, button down shirt, no tie, and a nice pair of ‘dressy shoes” (You can tell I’m no fashionista).  The combo says relaxed, but clean.

Now, lets talk jewelery. Lately I’ve been seeing a lot of guys accessorizing with too much jewelery- that was odd for me to even type.  Here’s how I see it on a first date:  A watch is acceptable, and maybe even encouraged, but make sure it goes with your look. Don’t wear a super fancy watch with jeans, just don’t.  Don’t wear rings. Your class ring from 1998 is absurd and unattractive.  A small chain around your neck is acceptable, but keep it tucked in your shirt. Stay away from heavy necklaces- she’s in to YOU, not Mr. T. and I pity the fool who thinks otherwise.

Hats.  ugh.  I dislike hats on a first date unless you’re going to a ball game or a hoedown.  You may keep women around with your charm, but you win them with your eyes.  Let her gaze.

Facial hair is a toss-up, really.  I think in your situation, the safe bet is to wear your facial hair like you would for work.  So if you’re clean-shaven at the office, be clean-shaven for her until she says otherwise.  If you are a member of ZZ Top, then maybe you should keep the beard- just promise me you’ll brush it.

I think that covers most of the basics.  If you have any other questions, please ask, because I’m sure I left something out.  Good luck, Jared!  Any of you women want to weigh in on this??  What are some of your first date turn on’s and turn off’s?  I’m sure Jared would love the advice.

9 comments on “ask sabatino- proper date attire

  1. My FAVORITE is when a guy smells like soap and water. Also, is wearing a great sincere smile. You can’t go wrong when he just genuinely looks like he wants to get to know you as a person (not as a potential girlfriend or wife, yet).

    • That’s a good point. You don’t want to wreak of too much cologne, like you just stepped out ot a French whore house, but the “clean” smell is always a crowd pleaser- and you can’t go wrong with a smile.

  2. Also, you spelled “marriage” wrong.

  3. Jared when is your date? Sorry to be so nosy but I’m rooting for you buddy! I’m a female gazer on dates especially first dates. I will take you in from head to toe not because I’m judging you or anything but because first impressions speaks volumes. Your “look” allows me to measure how important this date is to you. It’s pathetic to some and a deal breaker for others but you won’t know where she falls until you meet her that’s why you should follow your heart. I would check in and see how you feel and how you would like to “show up” on this date. I believe the more comfortable you are, the more your inner you shines and nothing is more sexy than being authentic. It shows you’re confident and ready.

    In 2012 I was a serial dater until I met someone by surprise that has been occupying my mind since I’ve met him. He hasn’t a clue about attire but I guess this time around it doesn’t matter… he has substance and that was the turning point.

    Good Luck!

  4. Good advice Sabatino but you better hope your date doesn’t take my advice because she will be way overdressed! ha

    • caligulamugler, since you’re here, what would you suggest Jared’s lady friend wears on this first date to a tapas bar? I love hearing the female perspective!

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