What to Wear on a First Date

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Women in white top

A friend (and reader) just wrote in to ask what to wear to a date in 2021. My brief answer was “cute eyeletty tops” such as the ones above (in any color, not just white), but let's discuss more…

Here's her question:

People in my state (including me!) are about to be fully vaccinated, so I'm beginning to think about going on first dates again. I used to just grab happy hour drinks in my work clothes, but now my work clothes are zelle leggings with holes in them and hoodies from college. I'm in the midwest, so we're not super formal (a lbd for a first date would be overboard) and I have a fairly large chest that needs to be accommodated into a top. I have jeans from the before, but no “date tops.” What are your favorites?

I responded:

Oh good question! My vote would be for soft tops that are tactile/nice to touch and/or some of the eyeletty things out right now (I just updated an old post with a widget – Ann Taylor, jcrew/factory, Boden) — but I’ll pose to the hive.

(Here's the widget update to the the white tops for work post with the eyeletty things; usual suspects like Ann Taylor, Boden, J.Crew, and Banana Republic are represented…)

I found a few more selections just to make a nicer graphic for the top of the post — white eyelet popped to mind because I know there's a ton out there in stores right now (I always do love a nice white top for spring) — but a lot of these come in black or other colors.

Pictured above: one / two / three / four (multiple colors) / five (multiple colors)

I told my friend we'd pose the question on what to wear on a first date to the Hive, given that I've been happily married for almost 12 years. But I went on a lotttttt of first dates back in my day (like, a lotttttt), and my theory on “what to wear on a first date” was pretty set in stone, at least with the guys I was trying to date back then. I think it all boils down to this: wear what you feel confident in.

{related: tips for online dating for smart women}

But of course I had a few more rules for myself that I thought might be fun to share and kickstart discussion — again, these are just the ones that I had for myself; I'm not necessarily saying they should be your rules…

  • Nothing requiring lots of yanking or adjusting (truly, #lifegoals)
  • No dresses or skirts (after I showed up to one lunch date in a sheath dress — because I'd come from work — and he immediately got weird and asked if I'd “dressed up for him.” (Even now I'm eyerolling hard — that should've been my first red flag.)
  • Nothing requiring Spanx or other shapewear (see above, but also because then it's awkward if the date goes well). (I have never liked my midsection, so a floaty top was always my favorite, but there are of course a ton of cute crop tops out there right now!)
  • Nothing with too much skin (but you do you!). For me, I think for me this was a comfort issue — if the first date turns out to be a total dud, as so many of them do, you don't want to be sitting there looking like HOT DATE when you're feeling more like “When can I go home and binge Netflix?”
  • But: bonus points if you can find something tactile (in winter, cashmere or a supersoft sweater works great!)

{related: finding time to date when you're superbusy}

In summertime, eyelet tops like the above would have been my go-to (with jeans) for a date. In fact, the eyelet tank at far left is similar to the black top what I wore on my first date with my husband. (That said, I did MEET my husband while wearing a black jersey dress from Banana Republic (and red heels) — but it was a friend's birthday party, so different “rules” applied.)

Readers, do tell — what's your advice on what to wear on a first date in 2021? Cute tops and jeans? Skirts and dresses? (How does footwear play into your planned outfit? I always wanted to feel comfortable walking several blocks in my shoes, so that further constrained some of my outfits…)

Psst:

Hunting for great books on dating when you're busy? Readers have loved Evan Mark Katz's work, and Kat thought this book on the technical side of flirting and body language was really helpful back in her dating days.

14 Comments

  1. There’s no right answer but I totally disagree with Kat’s advice to not wear a dress or a skirt. I am a believer that if you feel like you’re on a date, it feels more like a date. I always try to look a little special or more polished than regular. Helps get me in the mood!

    1. I had a rotation of sleeved fit and flare casual dresses I wore for first dates, usually with flats or flat sandals. Dresses made me feel feminine and pretty, and I didn’t have to worry about things matching. I could also wear them for more casual days at work.
      My first date with my husband I wore a long sleeved fall colored paisley dress and knee high boots.

    2. I haven’t been on a first date in a very long time, but I wouldn’t rule out a dress or skirt for myself. I am someone who doesn’t present as particularly feminine (more of a tomboy lawyer vibe, I guess?) and “flirty” top styles don’t work well for me for a bunch of reasons. So I tend to get a better reaction from men in social situations when I am wearing a simple skirt or dress. I have thought I could do a study of how much more often my BF and guy friends make casual physical contact with me when I am wearing a dress. Plus, with the current SEUS weather and mostly outdoor activities, I am finding midi and long skirts to be the most comfortable.

    3. I advocate the opposite of Kat’s advice: so long as you are comfortable in them, wear a skirt or a dress. Pragmatically, if it’s summer, jeans are really hot. You can wear Keds with a skirt and still look cute and dressed up; the same with jeans might signal that you didn’t put much effort into looking nice.

      1. On a first date though, I don’t want to look like I put in much effort! That’s for the second date, if I know I like the person.

        1. Would you go out on a second date with a man who looked like he put no effort into the first date?

    4. +1 I also never wear skirts/dresses to work (engineer) so wearing one helped me get out of work mode.

    5. Yeah I have a bunch of comfy, casual dresses that I wear all the time for dinner with friends, etc., that I wouldn’t consider “dressing up”. They’re easier than putting a whole outfit together, so if anything, they’re the lazy option! Especially in the summer when it’s too hot to wear jeans.

  2. I don’t thing any of the shirts pictured would look good on someone who is larger-chested (like myself and the reader who originally asked the question). Any better suggestions for us well-endowed ladies who don’t want the whole outfit to be ABOUT that fact (ie. in the way that any of the pictured necklines would).

    1. A boxy shirt (de-emphasizing the chest) but cropped (so you don’t lose all shape). I have lots of this type of tee from Madewell, which I wear with high-waisted jeans.

      1. Instead of boxed, I would do a half-tuck for this style, and roll the sleeves a little if they hit mid-boob.

    2. I like boat necks – and am very well endowed. A boat neck will show some skin, including the clavicle, but wont be an arrow pointing to your cleavage (hello v-necks), or just drapery on a boob shelf, which some higher necks feel like.

    3. There was a previous post for an eyelet top from Banana Republic that you might prefer. That top was, coincidentally, delivered to my house while I was reading this post. It is as pictured and the quality feels nice. It’s a white shirt that is not see-through (except the eyelet on the sleeves as intended)! Unfortunately, I will likely be returning it because I somehow overlooked the puff sleeves, which are pretty much always a no-go for my broad-shouldered physique.

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