It’s Date Night-Let’s Dress Up! What To Wear On The First Date

What to wear on a date seems to be as pressing a topic those of us over 50 as it is for our more youthful counterparts. We assume that it’s mostly women obsessing over clothes, but men have issues as well.

There is no one-size-fits-all answer for what to wear on a first date. It’s always a mystery trying to figure out what to wear and wondering if the two of you will be similarly dressed. There’s nothing worse than showing up in a suit and she’s in jeans, or vice versa.

So, by way of illustrating the topic I’m sharing my recent round of dates (all of which were ‘dead-ends’) with a short analysis of what worked and what didn’t work.

1. “J”- Sunday afternoon coffee date. Me-jeans, nice knit black top and flat dressy black sandals. Him-jeans (?) and a button up shirt. We sat outside and had a leisurely coffee. Perfectly appropriate for the setting and time.
2. “M”- Spur of the moment Saturday night dinner. First date, he said yes, then no, then yes again. I had on casual slacks and some type of blouse. He was dressed in jeans and t-shirt with  a vague bottom-of-the-laundry-basket smell. We had good conversation over a leisurely, expensive dinner that he paid for. He was looking for good conversation and sex. So, the dirty clothes didn’t really bother me as we weren’t going to be a good match.
3. “D”- Told me ahead of time that he always dressed casually. He was wearing a Hawaiian-type shirt (I think) and shorts. I wore jeans and blousy, casual tunic. Dinner in a place where casual worked.
4. “C”- Black slender jeans, nice shirt and black short boots. Me-white slacks,  white camisole top w/ short-sleeved sweater. We had dinner at a nice restaurant then drinks at club later. Worked just fine. I liked his style, but he chose the other woman he’d seen earlier in the week.
5. “A”- Showed up with his hair in ponytail (same as photo), jeans, t-shirt under unbuttoned nondescript plaid shirt. Me- jeans and nice blouse. Good meal in a fairly expensive restaurant on a Saturday night. He didn’t offer to pay. In his Peter Pan phase of life (his words) and just not for me. Has 16 house cats–that’s a non-starter.
6. “B”- Khaki pants and Brooks Brother knit short sleeve shirt. Me- black leggings and long white linen tunic (that covered rear and upper thighs), open to show a lacy camisole under the thin linen. A bit of a tease, but not much. Nice to average restaurant, he paid. We had a good time. Pleasant but lacking chemistry for both of us.
7. “P”- Shorts and nice knit shirt. He told me that he’d be in shorts, he was on break from college teaching. I was on my way to work so we met for morning coffee. I had on skirt and top and was overdressed based on his outfit, but it wasn’t really a problem. Never heard from him again.
8. “OM”- (that stands for old man, he was 76) Shorts, a striped t-shirt reminiscent of Where’s Waldo and a baseball cap which he kept on through 2/3′s of lunch. Me-floral skirt, nice top, sandals. I felt appropriately dressed and took his casual look to be indicative of the way he approaches dates/life, etc.  I had expected something slightly more dignified so his outfit and lack of manners was a disappointment.

Dates number 4 (architect) and 6 (therapist) win the prize for dressing appropriately for our first date. They looked comfortable yet clearly took a little time to try to make a good impression.

Sometimes clothes matter and sometimes they don’t.

This is such a personal thing that you can’t set absolute rules. Each of us has our own personal style and preferences. I was raised in The South where manners and a sense of respect or courtesy was stressed.  I like my men well-dressed, or at the very least I like to know that they can dress-up when the occasion demands it. In general, I find t-shirts unacceptable on a first date. Unless we’re going kayaking. I swoon over an expensive dress shirt.  I’ve been known to run my fingers down the arm of a man in a nice dress shirt… a rumpled t-shirt doesn’t stir my blood in quite the same fashion. You might want a rough-and-tumble, casual guy so jeans and t-shirt would be just fine for you.

The  first date is all about impressions. The two of you should be excited about meeting each other and looking forward to it. That means taking a little effort; not throwing on the first thing you come across. I always make an effort to look my best for a first date and even if I wear jeans, my blouse and accessories will be nice.

How you feel about his/her dress style will be based on a number of factors. If you’re looking for a socially active date who loves fine dining and attend plays and concerts you might gravitate more towards the well-dressed man. If you’re into camping and hiking, horseback riding and other active outdoor activities then casual wear might suit you. See what your date has on in each of his or her profile pictures to get a sense of ‘normal’ wear. Ultimately the decision about what to wear is personal. And the decision about your date will be based on a wide variety of factors, not just the clothes he or she wore on the first date.

Walker

Got a clothing story to share? Or a question? We’d love to hear it.