How to Organize a Stylish Road Trip from NYC to LA?

Isn’t it absolutely thrilling how our fashion choices evolve as we journey across the world? It’s almost as if every city has its own unique fashion personality. I think this is certainly the case in the United States. Imagine this: a fabulous journey through the chic streets of New York, the avant-garde avenues of Chicago, and the laid-back style of Los Angeles. With a variety of colors, fabrics, patterns, and silhouettes to experiment with, a road trip from NYC to LA brings you up close and personal with an endless array of urban styles. So, buckle up and get ready for some inspiration for a stylish road trip from NYC to LA!

Why the NY-LA Road Trip: The Inspiration behind the Fashion-Hub Cities

New York, Chicago, and LA – what ties these cities together is their rich fashion heritage. I believe that NYC, the fashion capital, seamlessly blends high-end couture with a streetwise edge. While you wander through NYC’s neighborhoods, such as the artistic boutiques of SoHo with their unique fashion pieces and the quick-changing world of fast fashion in Times Square, you’ll observe the city’s fashion scene morphing, much like a chameleon.

On the other hand, Chicago has a mix of grit and elegance. This city is famous for its impressive architecture and is a place where you’ll find a wide variety of vintage-inspired fashion. From industrial outfits to cozy and stylish looks for the cold months, Chicago’s fashion scene blends urban style with sophistication. Wicker Park, in particular, is a great neighborhood to find 20+ year old vintage shops, popular brands, and small boutiques. Here, alternative and thrift styles are popular, offering plenty of originality for you to incorporate into your own fashion story.

And then, as you drive into the sun-soaked lanes of Los Angeles, you’ll find casual elegance in full swing. LA is renowned for its laid-back Cali style that makes comfort fashionable. While celebrity sightings might dazzle you, I think that the street fashion is equally stunning. From Venice Beach’s boho-chic vibe celebrating free spirits to the glamorous style of Rodeo Drive (remember “Pretty Woman” with Julia Roberts and Richard Gere?), you can discover fashion inspiration as diverse as the city’s ever-changing landscape.

A road trip through these cities isn’t just about covering miles; it’s like flipping through the pages of a style lookbook!

man posing by street art
Photo by Chait Goli on

Vehicle Choice: Journeying in Comfort with a Mid-Size Truck

When you embark on a road trip from NYC to LA, your vehicle becomes more than just transportation; it becomes your second home. The thrill of exploration is amplified when you travel in comfort, keeping fatigue at bay. A mid-size truck offers the perfect blend – it’s robust enough for the long haul, yet compact enough for city parking. Just like your fashion choices, your vehicle should complement the essence of your fashion journey perfectly. Consider ample storage space for your fashion finds and the durability to take on diverse terrains when choosing a vehicle.

Make sure that your (rental) car is in its best condition. I have seen many people who ignore their car maintenance and go on a road trip without any precautionary measures. Apart from the daily maintenance, there are some steps that every driver should take before embarking on any long journey.

Exploring Local Wonder: Styles Along the Streets

Get ready for the thrill of exploring a mix of street styles during a road trip from NYC to LA. Each city weaves its fashion tales right into its busy streets, like a live fashion show that changes with every corner you turn:

New York – The Ultimate Fashion Catwalk

New York City, a fashion lover’s paradise, offers a dynamic fashion scene that’s ever-evolving. Whether you prefer high fashion or street style, NYC provides endless opportunities to indulge your fashion passion. Here are some top activities:

  1. Visit Fashion District: Explore the Garment District, home to countless fashion showrooms, fabric stores, and fashion studios. You can take a guided tour to learn about the history and inner workings of the fashion industry in NYC.
  2. Go Shopping: NYC offers world-class shopping opportunities. Visit iconic department stores like Saks Fifth Avenue and Bergdorf Goodman, explore luxury boutiques along Fifth Avenue and wander in trendy neighborhoods like SoHo, Williamsburg, and the Lower East Side for unique finds. NYC also has a thriving vintage shopping scene. Stores like Beacon’s Closet, What Goes Around Comes Around, and Buffalo Exchange offer unique vintage and second-hand clothing.
  3. Museum Exhibits: Check out fashion-related exhibitions at museums like The Metropolitan Museum of Art’s Costume Institute and the Museum at the Fashion Institute of Technology (FIT). They often feature impressive collections and fashion history displays.
  4. Fashion Shows: Keep an eye out for fashion shows and events. NYC hosts Fashion Week in February and September, but there are also other fashion events and shows throughout the year.
  5. Trendspotting: NYC is where many fashion trends start. Keep an eye on what locals are wearing and take inspiration from their style.
  6. Fashion Workshops: Participate in fashion-related workshops and classes, from sewing and pattern-making to styling and fashion illustration.
  7. Fashion Photography: Explore locations and spots popular for fashion photography, like DUMBO, the High Line, and the Brooklyn Bridge.
  8. Visit Iconic Fashion Landmarks: Don’t forget to take photos in front of iconic fashion landmarks like the Fashion Walk of Fame and the Carrie Bradshaw steps from “Sex and the City.”

Chicago – A Fashion-Forward Blend

Chicago’s fashion scene is a rich tapestry of styles and influences. Here are my favorite fashion-related things to do in Chicago:

  1. Go shopping: Shop along Michigan Avenue, known as “The Magnificent Mile”, which boasts a wide array of luxury boutiques and department stores. Other great shopping areas in Chicago are Oak Street in the Gold Coast neighborhood (upscale boutiques, luxury stores, and high-end fashion), Wicker Park (vintage stores, boutiques, and alternative fashion styles) and State Street (mix of well-known retailers and affordable fashion options). Stores like Crossroads Trading Co., and Kokorokoko offer thrift shopping experiences.
  2. Chicago Fashion Incubator: Visit the Chicago Fashion Incubator at Macy’s on State Street to learn about local emerging designers and their creations.
  3. Museum Exhibits: Explore fashion-related exhibitions at museums like the Chicago History Museum and the Museum of Contemporary Art Chicago and learn about Chicago’s historical significance in the fashion industry, especially in menswear and retail.
  4. Chicago Fashion Shows: Attend local fashion shows and events to see the work of emerging designers and to keep up with the latest trends.
  5. Fashion Workshops: Participate in fashion-related workshops and classes, including sewing, pattern-making, and styling.
  6. Street Style Photography: Capture street style moments in neighborhoods like Wicker Park, Logan Square, and Pilsen.

Los Angeles: Comfort as the Epitome of Fashion

Los Angeles is a major fashion hub with a diverse and vibrant fashion scene. Here are some of the best fashion-related things to do in Los Angeles:

  1. Go shopping: Explore the Fashion District in downtown Los Angeles if you like wholesale showrooms, fabric shops and boutiques. Other great places to check out are the iconic Rodeo Drive in Beverly Hills (known for its luxury boutiques and designer stores), The Grove (a popular outdoor shopping and entertainment complex), Abbot Kinney Boulevard in Venice Beach (known for its eclectic mix of boutiques, art galleries, and unique fashion finds) and thrift stores like Jet Rag, Wasteland, and American Vintage.
  2. Museum Exhibits: Visit museums like The Getty Center and the Los Angeles County Museum of Art (LACMA), which often host fashion-related exhibitions and displays.
  3. Street Style Photography: Capture street style moments in neighborhoods like Silver Lake, Arts District, and Downtown Los Angeles.
  4. Attend Fashion Events: Keep an eye out for fashion shows, pop-up markets, and fashion-related events happening in the city throughout the year.
  5. Eco-Friendly Fashion: Look for stores and events focused on sustainable and eco-friendly fashion, which is a growing trend in Los Angeles.
  6. Hollywood Walk of Fame: Take a walk along the Hollywood Walk of Fame and observe the fashion history and style associated with Hollywood’s stars.
  7. Melrose Avenue: Wander along Melrose Avenue, a trendy street lined with fashion boutiques, vintage shops, and streetwear stores. It’s a hub for unique and alternative fashion.

Creating the Wardrobe: Chic Comfort is Key

A fashion road trip requires a wardrobe that’s not only chic but also incredibly comfortable. Your fabrics should breathe, your designs should offer a comfortable fit, and every outfit must be photo-ready!

Check the weather forecast for each city you’ll be visiting and pack accordingly. NYC can be cold in the winter, Chicago experiences all four seasons, and LA is generally warm, but it can get cool in the evenings. Think relaxed-fit denims that allow for easy movement as you explore new cityscapes, flowy maxi dresses that capture the essence of LA’s relaxed vibe, dainty tops for a touch of elegance, and oversized blazers that effortlessly transition from day to night.

Spice things up with chunky accessories or experiment with unique color palettes to create that effortlessly stylish look that’s perfect for the road. After all, you’re not just traveling; you’re making a statement with your style at every stop along the way.

Tip: I’ve collected 20 must-have travel accessories for women to get you started. I hope this list makes packing easier for you.

Additional tips for a stylish road trip from NYC to LA

Here are some additional tips for a stylish road trip from NYC to LA:

  1. Fashion Apps: Use fashion apps and websites to discover local boutiques, vintage shops, and fashion events in each city. These can help you plan your shopping and style adventures.
  2. Fashion Magazines: Bring along fashion magazines for inspiration and to stay updated on the latest trends.
  3. Hydration and Snacks: Staying stylish also means staying comfortable. Keep water and snacks in the car to stay energized during the journey.
  4. Plan Your Route: Plan your route to include time for shopping, fashion exhibits, and other activities in each city.
  5. Personal Style Journal: Bring a journal or use your smartphone to document your journey, making note of favorite fashion finds and outfits. One of my favorite apps to do this is ‘Polarsteps‘.
  6. Music Playlists: Create a stylish playlists to set the mood and enhance the overall experience.
  7. Take a spectacular road trip from Las Vegas: dedicate some time to explore the Las Vegas area away from the Strip. The city is perfectly positioned to give you some amazing experiences.


In this road trip from NYC to LA, you’ll embark on a fashion journey that’s as diverse as the cities themselves. New York, Chicago, and Los Angeles each offer a unique fashion experience. As you explore, your vehicle choice matters and your wardrobe should be a mix of chic and comfortable, adaptable to different climates. Capture the street styles of each city and make the most of your visit with our fashion tips.

In New York, discover the ultimate fashion catwalk. Chicago blends grit and elegance, while Los Angeles epitomizes casual comfort. Whether you’re shopping, attending shows, or exploring, embrace the fashion diversity of this epic road trip.

Document your journey, stay inspired, enjoy the diverse fashion landscapes ,and have fun as you explore these fashionable cities. Safe travels and happy styling!

If you have any questions about the above mentioned information, please let me know in the comment section below. I’m happy to help you. Safe travels!

Author: Daphne

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