woman wearing a dress with a faux leather skirt and a sweater top

Heading to out for a night at the theater this winter or just want an elevated date night look? This week’s What to Wear board showcases a rich chocolate brown palette, a trend we’re seeing a lot in fashion trends for women over 50 this season.

The faux fur jacket adds a touch of luxury, while this faux leather dress steals the show but is equally comfortable for a night out. The statement clutch and gold embellished suede heel complete the look with a touch of sophistication.

Pro tip: when choosing your date night outfit for, opt for a shorter coat like the one featured here. This way, you can skip the coat check lines and head straight to your seat. You won’t have to worry about bulky outerwear taking up precious space where you are seated.

what to wear to the theater, an all brown outfit with a faux leather dress, faux cropped jacket, gold studded handbag, brown suede gold embellished heels from dolce vita and brown leather cashmere gloves
Shop This What to Wear Look

So, whether you’re planning a romantic date night at the theater, ballet, Broadway show, or just want an elevated winter date night outfit idea, this What to Wear board provides the perfect inspiration for a chic and stylish theater experience.

Key takeaways from this What to Wear board:

  • Embrace the chocolate brown trend, a popular choice in fashion trends for women over 50 this season. While I am not one for fast fashion trends, this one is going to be around awhile; browns are so versatile.
  • Opt for cozy and comfortable pieces that are still stylish and sophisticated.
  • Choose a shorter coat for ease of movement and storage while out.

Remember, confidence is the best accessory! So, step out in style and enjoy your date night.

Additional tips for your What to Wear on a date night:

  • Consider the dress code and dress accordingly.
  • Choose comfortable shoes that you can walk in easily.
  • Accessorize with statement jewelry or a scarf to add a personal touch.
  • Most importantly, have fun and enjoy the evening!

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