Brenda’s Travel Tips for Business Trips

By Brenda

Traveling for business while embracing your crossdressing identity can be both exciting and challenging. With the right strategies, you can ensure your trip is smooth and enjoyable. Here’s a guide to help you navigate packing, managing your wardrobe, and checking in with confidence. With these tips in mind, you’ll be well-prepared to handle your business trip with both professionalism and personal flair. Enjoy the experience of balancing your professional responsibilities with your unique style.

Brian's Journey to Becoming Lena: Embracing Personal Identity on the Road

Brian was no stranger to the world of business travel. As a seasoned consultant strategizing for big-name clients across various industries, he was to travel to New York for a crucial business presentation. Used to the usual business attire—a crisp suit, polished shoes, and a neatly tied tie—Brian also had a special tradition he looked forward to on his trips. When the workday ended, he would embrace his love for crossdressing, slipping into outfits that allowed him to express his personal style. His transformation into Lena, an iconic persona of an international business woman on the move, was both a personal ritual and a moment of self-expression. She wanted to make sure her wardrobe choices matched both her professional style needs and her personal comfort.

As Lena packed her bags, she thought of her top tips for blending style with practicality while on the road. She knew these could benefit others as well.

1. Pack Smart with Versatility

Lena knew that packing light yet versatile was key. She chose outfits that could seamlessly transition from day to night. Her wardrobe consisted of a classic blazer, chic trousers, a pencil skirt, and a selection of blouses in neutral colors. Each piece could be mixed and matched, creating multiple outfits without the bulk of extra clothing. She knew she would be a tourist for two days and have two evenings free. She drafted a quick list of clothing based on the planned weather conditions, aiming to present as a successful, middle-aged business professional when out and about. She considered bringing a little black dress (LBD) paired with a unisex-style trench coat as well. "Hmm, I doubt I can do carry-on this trip," she mused. "Most likely, I'll need to check baggage, which saves me from seeing what high heels and bras look like on the X-ray scanner."

What to Pack

Clothing

Business Attire: Pack a versatile selection of business outfits, including a well-fitted suit, blouses, skirts, trousers, and blazers. Opt for items that mix and match easily.

Casual Wear: Choose a few casual outfits for downtime, such as comfortable dresses, leggings, or jeans paired with stylish tops.

Accessories: Lena packed a few versatile accessories—scarves, a red belt, statement necklaces, and classic earrings—that could elevate any outfit without taking up much space. She also included a stylish, lightweight unisex trench coat suitable for New York weather, adding a polished touch to her look. A clutch is easier to pack than a purse.

Shoes

Pack a pair of black pumps with a block heel, a stiletto open-toed sandal, and flats.

Pack Shoes Wisely: Place shoes in separate dust bags or plastic covers to keep them from scuffing your clothes. Stuff them with socks or other soft items to help them retain their shape.

Grooming and Makeup

Grooming Kit: Pack a compact grooming kit with essential items like razors, tweezers, nail clippers, and a hairbrush.

Makeup: Include your favorite makeup products in travel-sized containers to save space. Don’t forget essentials like foundation, mascara, lipstick, and any specific products you use. A clean, light look is preferred to heavy makeup.

2. How to Pack

Use Packing Cubes

Organize by Category: Separate business attire, casual wear, and accessories using packing cubes or pouches. This will make it easier to find what you need quickly. I use a yellow ribbon to denote femme attire.

Protect Delicate Items: Use garment bags for delicate or easily wrinkled clothing, such as dresses or blouses.

Roll vs. Fold

Roll Clothes: Rolling clothes can save space and reduce wrinkles, especially for casual wear.

Fold Carefully: For business attire, folding neatly and placing them in garment bags can help maintain a crisp appearance.

3. Prioritize Comfort and Fit

Comfort was non-negotiable for Lena, especially when traveling. She selected breathable fabrics and well-fitting garments that allowed for movement and didn’t require constant adjustment. Her chosen heels were stylish but low enough to avoid foot fatigue. "Choose a bigger heel base, as stilettos will not work for long walks along 5th Avenue," she advised. "As a middle-aged woman experiencing menopause, comfort and fit are very important. I don’t want to get too hot and worry about my makeup or sweating profusely on humid days. This is probably why I enjoy the fall season... cool and crisp."

Tip: Choose fabrics like cotton blends or stretchy materials that provide comfort and flexibility. Well-fitted shoes and accessories that don’t pinch or dig in are essential for long days on the go.

4. Master the Art of Grooming on the Go

For Lena, grooming was a critical part of her travel routine. She packed a compact grooming kit with essential items like makeup, a travel-size hairbrush, and a lint roller. In fact, she had both a male and female grooming kit.

Tip: A well-organized grooming kit can save you time and stress. Keep your routine simple but effective, and ensure you have all the basics for quick touch-ups.

5. Checking in En Femme

Lena had only checked in en femme twice, and the second time, the experience was incredibly nerve-wracking due to an anti-LGBTQ+ motel manager causing a scene. However, she had left many hotels as Lena and returned as Lena multiple times, feeling safe. Even with the elevator apprehension causing anxiety, it usually wasn’t a problem. Now, smartphone check-in allows you to go directly to your room without any front desk intervention. I personally do not present as a female in any Hotel lobby bar to avoid followers, well actually those men who then decide to follow me to my room or trying to hit on me hard.

Confidence is Key: When checking in, approach the front desk with confidence. Your attire is a personal choice and should be respected by the staff.

Be Prepared for Questions: While most hotel staff are accustomed to diverse guests, be prepared to answer any questions with professionalism and composure.

Room Privacy: Use "Do Not Disturb" signs to avoid unexpected interruptions.

Research hotel policies regarding room reservations and dress code. Most hotels are LGBTQ+ friendly, but it’s good to be informed.

Bring identification that matches your travel documents.

Research local LGBTQ+ friendly spots or communities in your destination. It can be helpful to know where to find supportive environments or shopping options. Lena once attended a local "Gurlz" dinner from a forum invite and enjoyed it because she knew there were 12 other "Gurlz" attending.

By the end of her trip, Lena had not only achieved her business goals but had also embraced her personal style with grace. Her journey was a testament to the power of thoughtful preparation, proving that with the right approach, crossdressing while traveling for business could be both stylish and effortless.

Conclusion: A Journey of Balance and Self-Expression

As Brian arrived in New York and took a yellow taxi to his hotel, he began becoming himself as Lena and his mood shifted, feeling confident and ready. Her meticulous planning was going to pay off. During the week, Lena planned to attend museums, art galleries, window shop with poise and elegance and explore the city in her favorite outfit.

The day had been a travel whirlwind with flight delays and Brian was eager to unwind. As he checked into his hotel room, he smiled, thinking about the evening ahead. In his room, room service was ordered while Lena unpacked her special bags—a sleek, discreet packing case that contained her female wardrobe. She was excited to finally wear the elegant dress she had chosen for this trip: a fitted black dress with delicate lace details. The dress was complemented by a pair of open-toed pumps and a matching clutch. Lena carefully laid out each item on the bed and took a moment to admire the outfit. It was her way of balancing her professional life with her personal passions.

The transformation was both thrilling and soothing. She began with a warm bath, followed by a meticulous grooming routine. Lena enjoyed the process of choosing the right makeup, applying it with precision and making sure everything was perfect. The final touch was a spritz of her favorite perfume. As she looked in the mirror, she felt a wave of satisfaction. The dress fit perfectly and she felt both elegant and empowered. Confident and apprehensive she was ready to venture out into the world.

With a contented sigh, Lena headed out of the hotel room before the dreaded fear changed her mind (there is always that voice in the back of your head telling you not to do it). New York is known for its vibrant nightlife and charming streets and is relatively safe and LGBTQ+ friendly. She decided to start the evening with an early dinner at a quaint bistro recommended by local crossdressers. The restaurant had a cozy ambiance and a reputation for excellent cuisine with a quiet service approach. This was a perfect way to relax and just enjoy the moment.

Walking through the city streets, Lena enjoyed the feeling of the cool evening air and the subtle click of her heels against the pavement. Her dress swayed gently with each step and she couldn’t help but smile at the admiring glances she received. She felt confident and at ease, a stark contrast to the formal constraints of her workday.

At the bistro, Lena was greeted warmly and led to a table by the window, where she could enjoy her meal while people-watching. She ordered a glass of Chardonnay and the chef’s special for the night—a decadent seafood risotto. As she savored each bite, she felt a sense of liberation and contentment. This was her time, her space and her moment to be unapologetically herself. After the delicious dinner, Lena decided to explore a bit more. 

The meal was exquisite and Lena took her time enjoying each course, savoring every moment. She found herself chatting with fellow diners, who complimented her style and engaged her in light conversation. It was refreshing to connect with others in such an open, relaxed setting. Lena felt safe and accepted.

After dinner, Lena decided to stroll along Battery Park. The city’s iconic skyscrapers illuminated the night sky and the cool breeze felt invigorating. She wandered aimlessly, soaking in the sights and sounds of New York’s vibrant financial district, feeling a deep sense of liberation and joy. On a whim, she took the Staten Island Ferry, passing the Statue of Liberty. She felt liberated, the gentle wind in her hair and the glow of happiness spreading across her face. A couple of discreet selfies captured the moment to cherish later. This evening proved to be memorable for Lena, after years of balancing her dual identity.

As the night drew to a close, Lena returned to her hotel room, still savoring the evening’s experiences. Room service brought a bottle of Chardonnay and some cheese bites as she prepared for the following day's business meetings. The all-important makeup removal and moisturizing routine was carried out. She laid out her outfit for a day of touring art galleries in Soho and several museums—a full day of just enjoying the city and wandering wherever curiosity led her.

With a satisfied smile, Lena prepared for bed, already looking forward to her next adventure. She knew that every business trip was an opportunity to balance the demands of work with the joy of self-expression, making each journey uniquely rewarding.

While window shopping earlier, a moment of clarity struck her as she caught her reflection in the glass. The reflection wasn't an illusion but a real depiction of herself at this time, in this place, as she truly was—in mind, spirit and physical presence. What once felt like fantasy was now reality. Her mind shifted into a gentler, softer state and even her gait slowed and became more natural (well, she was wearing high heels). Lena’s anxiety and hyper-vigilance, though present, were now in the background, no longer front and center. With this newfound calmness, she carried herself confidently throughout the day, blending seamlessly into the bustling crowd of busy businesspeople navigating New York City.

This confidence and fearless approach gave her the courage to also take the subway (she had a Metro card ready), which was exhilarating—no one noticed her as they stared at their smartphones, playing Candy Crush or catching up on social media. She did this several times for short trips, loving every moment.

Not only did she enjoy public transit, but she also relished the ferry ride. Maybe next time, she would go up in a helicopter—that would be something, wouldn’t it? And what to wear—stockings or pantyhose? A mid-length skirt and ankle boots?

Wearing ModCloth

Kenyan femulator Dennis Karari