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As we slowly emerge from the pandemic and start attending events like the Epsom Derby, it’s natural to feel a bit lost when it comes to dressing up after such a long break. Louise, who reached out to our Wardrobe Whisperer column for advice, is not alone in this dilemma. The key is to rediscover your fashion confidence and embrace something new and exciting.

After two years of casual wear, the idea of formalwear may seem daunting. However, getting back on track doesn’t have to be complicated. Here are three simple rules to guide you through the process:

Rule 1: The Clothes
When choosing your outfit, consider the dress codes carefully. While the Epsom Derby is relatively lenient, other events like the Royal Enclosure at Royal Ascot have specific requirements. Opt for a midi dress, a jumpsuit, or a tailored suit, but make sure to adhere to the dress code guidelines. Solid colors are timeless, but don’t be afraid to experiment with prints if you find something truly beautiful.

Rule 2: The Shoes
Comfort is key when it comes to footwear. Opt for mid-height block heels or dressy flats to keep your feet happy throughout the day. Pointed toe slingbacks and minimalist mules are stylish and versatile choices. Avoid chunky flat sandals and make sure to break in new shoes before the event to prevent any discomfort.

Rule 3: The Hat
Contrast is key when it comes to choosing a hat for the races. Instead of matching your hat to your outfit, opt for a headpiece that stands out and adds a finishing touch to your look. Supporting British milliners is a great way to find a timeless piece that can be worn with various outfits for years to come. Padded hairbands and fascinators are acceptable at most events, but make sure to check specific requirements, like the size of the headpiece for Ascot’s Royal Enclosure.

By following these simple rules, you can confidently navigate the world of formalwear and make a stylish comeback after a long break. Embrace the opportunity to experiment with new styles, colors, and accessories to create a look that truly reflects your personality and fashion sensibilities. Join the conversation and share your fashion tips for dressing up after a long break.