9 Cute Outfits to Wear for Your Anniversary Date

The good news is if you’re at the point where you’re celebrating an anniversary with someone, it’s likely you feel comfortable wearing anything in front of them. The bad news, however, is that the A word often puts a degree of pressure on the date’s participants to, in short, step up their game. Whether it be by planning a special evening or, as we prefer (and the topic of today’s post), wearing an especially amazing outfit, you want to do something to show your S.O. that this day is important to you and that you’re grateful to be reaching such a milestone together.

So in the event that you’re the lucky one who gets to simply show up for the date looking like yourself 2.0, today we’ve got you covered with nine outfit ideas that are totally relatable, fashionable, and, most importantly, anniversary-worthy. Keep reading to see the outfits, courtesy of some of our favorite street style stars, and shop some of the pieces you may not already have in order to get the look.


Crop Top + High-Rise Jeans + Pumps
(Image credit: A Love Is Blind)


Lace Midi Dress + Heeled Sandals
(Image credit: Collage Vintage)


Blazer + Black Pants + Heels
(Image credit: Collage Vintage)


Lace Camisole + Button-Up Skirt + Pumps
(Image credit: Style du Monde)


Floral Minidress + Flats
(Image credit: Collage Vintage)


Sheer Detail LBD + Statement Shoes
(Image credit: Collage Vintage)


Blouse + Leather Miniskirt + Heels
(Image credit: Style du Monde)


Statement Top + Jeans + Non-Basic Flats
(Image credit: Style du Monde)


Wrap Minidress + Contrast Heels
(Image credit: Style du Monde)

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. It was a less expected route, seeing as she was graduating from business school at USC when this all began, but it has turned out to be the best one for her. Fast-forward to 2024, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was an intern starting out. Currently, she focuses on a weekly mélange of shopping content. As far as her personal style goes, she's largely drawn to classic pieces and neutral basics but will always make an exception for something colorful, printed, or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a good party is dressing up for one. On weekdays, she can usually be found at home eating something delicious for dinner and trying to force her husband to watch Summer House.