What to Wear on First Dates

Deciding what to wear on first dates should be a piece of cake . . . if you put a little thought and planning into it.

Dating, especially in the early stages, can be nerve-racking and stressful.

You can take some of the pressure off by having first dates be coffee dates.

Meet at a coffee shop or somewhere that you can grab a coffee and sit inside or outside for your date.

Coffee dates mean casual dress, which usually makes deciding what to wear less stressful.

And coffee dates allow you to more easily and quickly end the date, if things don’t go well.

If you meet for lunch or dinner, you may feel you have to sit it out until the meal is over.

I had many first dates in my over 60 dating life.

In my experience, women typically put much more thought into what they wear (on dates or for anything) than men do.

I had several first dates who showed up looking (and smelling) like they’d just finished mowing the lawn, or had done some kind of manual labor minutes beforehand.

And several who paid no attention to how awful their breath was. How hard is it to just pop in a mint before you walk into a date?

Keep this in mind: If he doesn’t care enough to look presentable on a first date, he’s showing you what his normal state is.

Most people understand that you want to make a good impression on the first date, so you put your best foot forward.

Will Rogers is credited with saying:

You never get a second chance to make a good first impression.

If your date shows up looking unkempt and unclean, things are likely to get worse, if the relationship progresses.

THE key element in what to wear on a first date

As a woman, I found that wearing something comfortable was at the top of my list when deciding what to wear.

Your comfort will translate to more confidence in the way you’re presenting yourself, and confidence makes you more attractive and appealing.

Think about all the clothing options for women for a casual or semi-casual first date:

• Long dress
• Mid-length dress
• Short length dress
• Long skirt and top
• Mid-length skirt and top
• Short skirt and top
• Pantsuit and top
• Trousers and top
• Jeans or other pants and top
• Shorts and top
• Suit jacket with skirt and top
• Suit jacket with trousers or other pants and top
• Super high heels
• Moderate heels
• Flat shoes or sneakers
• Jewelry and accessories
• A wide range of make-up choices

I’m sure there’s more, but you get the idea. Women are faced with many more choices to assess, before walking out the door and meeting with someone who may be their ideal partner.

Compared with those for men:

• Trousers and top
• Jeans or other pants and top
• Shorts and top
• Suit jacket with trousers or other pants and top
• Flat shoes or sneakers

Men have much fewer choices to sift through.

Men’s clothing is almost always designed for comfort. Women’s often is not.

Women: What to wear on a first date

With the many clothing options we have, it makes sense to take the time to try things on and put the outfit together well ahead of time.

You don’t want to show up late to your first date, so avoid scrambling at the last minute to pull things together.

Give yourself time, if you’re going to buy a new outfit.

Allow time for shopping and maybe wearing it for a bit around the home, to be sure it’s comfortable.

Allow time to wash or have things cleaned that need it.

The good news, you can wear the same outfit for every first date, if it works with the weather forecast and location of the date.

With comfort in mind, choose:

• Clothing that won’t ride up when you sit down, perhaps exposing something you don’t want to expose.
• Clothing that is not so revealing you’ll risk having the man stare at some part of you other than your eyes.
• Clothes or accessories that won’t keep you fidgeting to straighten things. That could signal to your date that you’re disinterested.
• Jewelry and accessories that won’t leave you worrying they’ll fall off or cause discomfort.
• Shoes that you can walk on steadily and that will be good for walking, if you decide to do so on the date.
• Makeup that is lightly applied enough not to run or smudge. You may not want to risk false eyelashes that could fall off.

I always wore nicely fitting jeans and a knit top with either sneakers or flat walking shoes. I never wear makeup. Remember, my first dates were almost always coffee dates, so my casual attire made sense for me.

Men: What to wear on a first date

You have fewer choices to sort through, but you will still benefit from choosing what you’ll wear well in advance of first dates.

Since comfort typically rules with men’s clothing, I don’t need to stress that you should choose an outfit that fits comfortably, and won’t shift in ways that make you fidget.

Allow time well in advance to wash or have things cleaned that need it.

Like for women, you can certainly wear the same outfit for every first date, depending on the weather and location.

On our first date, Cosmo wore close- but well-fitting jeans, and white oxford shirt and a navy suit jacket.

Now, I’m not saying that men must wear a suit jacket, but the fact that he did sure made a strong impression on me.