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.
Available in sizes XS to L.
Available in sizes 34 to 42.
Available in sizes 35 to 41.Up next: Seven more date outfits you’ll love for any occasion.
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. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.
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