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Friday, June 18, 2021
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What to Wear on a First Date in 2021

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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:)

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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.

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!)

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…)



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