Los Angeles doesn't really get winter. It gets a short season of low golden light, clear skies after the rain, and afternoons that are perfect for putting the top down. From now through spring, the city also has its busiest stretch of celebrations: holiday parties, proposals, New Year's Eve, then awards season, which runs from the Golden Globes on Sunday, January 10, 2027 to the Oscars on Sunday, March 14, 2027.
At Legends, we've been putting people behind the wheel of vintage cars in Los Angeles since 1999. This guide covers our open-top classics, how a classic convertible rental in Los Angeles works, and how to plan a holiday photoshoot, a proposal or an awards-night arrival around one.
Why a classic convertible in Los Angeles (and why now)
Summer gets the attention, but late fall and winter are the best convertible months in LA. The light is softer, the haze clears after a storm, and sunset arrives early (around 4:45 p.m. in December). That means a golden-hour photoshoot can finish before dinner.
There's also a calendar reason. Between Thanksgiving and the Oscars, Los Angeles stacks up more "arrive like you mean it" occasions than at any other time of year:
- Holiday card and family photos. One vintage convertible in the frame, and nobody needs matching sweaters.
- Proposals and engagement shoots. December is peak proposal season. A '55 Speedster on a coastal road says the rest.
- New Year's Eve and New Year's Day. Pair a convertible with our Rose Parade & Rose Bowl 2027 guide if you're heading to Pasadena.
- Awards season. Viewing parties, after-parties, press portraits and branded content around the Golden Globes and the Oscars.
- Valentine's Day. Sunday, February 14, 2027, sitting right in the middle of awards season.
Our classic convertibles, compared
Every car below is part of our classic car rental collection, maintained in-house and delivered detailed, with a personal meet-and-greet.
1955 Porsche 356 Speedster (black or silver): the European icon
Two seats, a manual gearbox and the most recognizable silhouette of the 1950s. The black Speedster runs black on red with chrome details. The silver Speedster is the cooler, more timeless take. Choose a Speedster for proposals, couples' shoots and editorial portraits, when the car and two people are the whole story.
Good to know: it's a manual. If nobody in your party drives stick, choose an automatic.
1965 Ford Mustang convertible (red or blue): the American icon
Four seats and a V8 soundtrack, and nothing reads "California" faster on camera. The red '65 Mustang pops in every frame. The blue '65 Mustang is calmer and coastal. We wrote a whole post on why to rent a Mustang convertible in Los Angeles. The short version: it's the friendliest classic to drive and the easiest to fit four people in.
1969 Ford Mustang convertible (black on black): the after-dark option
The black-on-black '69 Mustang is the moodiest car in the collection. For a New Year's Eve arrival or an awards-week after-party, it photographs beautifully under city lights.
1961 Buick Electra convertible (white): the bridal favourite
Full-size, bright white with a red interior. The 1961 Buick Electra is a natural fit for winter weddings and holiday photos with the whole family around it.
1967 and 1970 Cadillac DeVille convertibles: Old Hollywood glamour
If your plans involve a gown, a tuxedo or a red carpet, start here. The white 1967 DeVille is graceful and understated. The red 1970 DeVille with its white interior is pure '70s grand entrance. These are the cars we suggest most for awards-season arrivals.
You can browse every car by decade on our 1950s, 1960s and 1970s pages, or see the full lineup on the vehicles page.
Planning an awards-season arrival in a vintage convertible
Awards season brings premieres, screenings, viewing parties and after-parties across Hollywood, Beverly Hills and West Hollywood. A few things we've learned from 25+ years of LA productions and events:
Plan your driver for the big nights
On Golden Globes night (Beverly Hilton) and Oscars night (Dolby Theatre at Ovation Hollywood), the streets around the venues are heavily controlled. Plan the drop-off point and parking before the night, and pick a driver from your group who is 25+, licensed and insured. See our special-occasion rentals. Note that arrival access at official ceremonies is set by the event organizers, not by us. Confirm your drop-off point with your host.
Plan around the top
The top goes up as easily as it comes down. If rain is in the forecast, we'll talk you through the options when you book. For anything formal, many clients ride top-up and drop it for the final approach and photos.
Shooting content or press portraits?
Classic cars have been regulars on LA sets for decades. Our photoshoot and film car rental page covers how productions book with us. For a commercial shoot on public property, check permit requirements with FilmLA before the day.
Holiday photoshoot ideas within our service area
Classic car service covers a 50-mile radius from our Inglewood lot, which takes in almost every iconic LA backdrop:
- Pacific Coast Highway toward Malibu. Ocean on one side, cliffs on the other, best at golden hour.
- Palos Verdes coastline. Quieter roads and dramatic bluffs, close to our lot.
- Downtown LA and the Arts District. Brick, murals and city lights for a New Year's Eve mood.
- Pasadena's tree-lined streets. Craftsman homes and holiday lights. Tie it into a Rose Parade weekend.
- Your own driveway. Honestly, the easiest holiday card shoot there is. We'll deliver the car to you.
How classic convertible rental works at Legends
- Rates: classic cars start from $549/day (see pricing). Your exact rate depends on the car, date and occasion.
- Mileage: 50 miles per day included. Additional miles are $1.50 per mile. Most photoshoots and evening events stay comfortably inside that.
- Service radius: 50 miles from our Inglewood office. Beyond that, the renter is responsible for mechanical issues, breakdowns and towing.
- Self-drive: your choice on every car.
- Requirements: every driver must be 25+ with a valid license and proof of their own insurance (insurance is not included), plus a major credit card. The security deposit is released 1–7 business days after the rental closes out.
- Delivery: LAX terminal delivery and collection is $95 each way with 48 hours' notice. Delivery anywhere else is quoted per trip.
- Where we are: 204 Hindry Ave, Inglewood, five minutes from LAX. We're open Mon–Fri 9–5 and Sat–Sun 9–4, with after-hours pickup and return by prior arrangement.
Book early for December and awards season
We have one of each car, and holiday weekends and awards-season Sundays are the first dates to go. If you already know your date, lock it in now.
Ready to book? Holiday weekends and awards-season Sundays go first, and we have one of each car.
Check availability and book your classic convertible →Prefer to talk it through? Call or text 888-329-1898, or request a quote. Planning a wedding instead? Start with our wedding car rental guide.