What to wear- *SPECIAL* anniversary date?

posted 3 years ago in Dress
Post # 3
10219 posts
Sugar Beekeeper
  • Wedding: December 2012

Hi @MIBeeAlex:  First & Foremost as this is your DEBUT Post on WBee… a BIG Welcome to “the Hive”

In my first marriage (circa 1980), I knew precisely WHEN we would be celebrating our Engagement as the Ring had been picked out beforehand, and was to be picked up that Weekend.

So Yes, I went out and bought a special outfit for the occasion… a cream dress.  Very pretty.

When you have “a hunch” but you do not know for sure the timing, things will be a tad more tricky… as you say, can you keep wearing NEW outfits every.single.date ?

I will tell you this tho…

Statistically… More men propose between Thanksgiving & Valentines… and they typically do it around a Holiday, Occasion (Birthday, Anniversary etc) or on a Getaway… and often in a “special” place

So if your 5th Date-iversary is in December around the Holidays, I’d say that chances are GOOD that might be when it happens… so you’ll want to look great that particular day for sure.

Hope this helps,


Post # 4
613 posts
Busy bee

@MIBeeAlex:  Welcome to the hive! So I am in a similar boat! SO and I are going on vaca in a few weeks we are going with friends but I think he is proposing. we desided to do a date night on our own so I bought a super cute maxi for the occation.  BUT to be safe I have a cute outfit planned for every night!

my “date night dress” but in navy! its a nulti way tie but might go with the low V

Post # 5
1849 posts
Buzzing bee
  • Wedding: April 2014

What about Rent the Runway? You could “borrow” something and if it didn’t happen that night, you’d still look smokin hot, and could return it for something for when you have another hunch. 

Post # 6
71 posts
Worker bee
  • Wedding: August 2015

@Mrs Canuck:  this is a great idea!


OP, I have totally over-obsessed on outfits thinking that it was “the night” and (even though it hasn’t happened yet) it was always worth it to feel extra gorgeous and put together. Rent the Runway would be a great idea, or a used-designer website like Poshmark or EdropOff.  For myself, I have a silk/cotton blend dress by Alice McCall that I picked out for a possible-proposal date, and now that it’s the holiday season I have a sequined deco dress (a la All Saints) that I’m trying to hold off on wearing until I’m SURE it’s “the night”. Maybe this sounds a little crazy, it’s just that SO is photography obsessed and I know there will be about 600 photos taken haha. So I guess my point is, it totally makes sense to pick out something special, and I vote that you maybe come up with a few top outfits that can work for different situations. I hope he proposes at your anniversary!!

Post # 7
147 posts
Blushing bee
  • Wedding: December 2016

What does he LOVE you in? My FI loves when I wear plain black with my hair down and “natural” (I have to style it, but it LOOKS natural to him I guess haha) and black heels.

Go with something along those lines.

How much do you have in your closet? because if you are not SURE he is going to do it this date you don’t want to end up buying dress after dress haha. Shop your closet some because I know I have SO much more in there than I even know. The rent the runway idea is good. or maybe hit up a TJ Maxx or Marshalls and buy a nice designer dress there for a fraction of the cost in a style that is very YOU so you won’t be wasting the money on a new dress if he doesn’t pop the quesiton

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