Summer’s demanding schedule of spontaneous trips and social obligations necessitates a refined approach to packing. Terrence O’Connor, a sought-after creative director known for his work with top-tier artists, shares his strategies for maximizing carry-on space with an emphasis on sophisticated, travel-ready ensembles.
Effortless Travel Style
O’Connor emphasizes preparedness, highlighting a moment he was Grammy-bound with only 15 minutes’ notice, relying on a well-chosen Saint Laurent suit. His nomadic lifestyle, often spending up to 60 consecutive days on the road, has honed his ability to pack efficiently and maintain composure across time zones, a philosophy he embodies with the adage, “Jet lag is a choice.”
Wearing a suit jacket and jeans on the flight is more than just a way to channel the first-class cool of ’90s A-listers strolling through LAX: It’ll spare you from frantically steaming the jacket once you reach your destination.Jacket, $1,280, by The Anthology. T-shirt, $250, by Emily Dawn Long. Jeans, $395, by Nili Lotan. Boxers, $40, by Brooks Brothers. Sunglasses (throughout), $420, by Saint Laurent. His own hat by Ferrari. Earring (throughout), his own. His own necklace (throughout) by Miansai. Bracelet (top), $290, by Chan Luu. His own bracelet (bottom, throughout) from Barneys New York. His own bag by Balenciaga. His personal brand is built on an impeccable, yet relaxed, sense of style that translates seamlessly from international flights to high-stakes creative meetings.
Curated Travel Wardrobe Essentials
The key to efficient travel packing lies in versatile pieces that transition effortlessly. O’Connor champions a “vacation commando” approach, layering adaptable separates that offer both comfort and polish.
Shirt, $1,470, by Louis Vuitton Men’s. Shorts, $144, by 18 East. Shorts (underneath), $75, by Patagonia. Sneakers, $99, by Village PM. Stylists’ own hat by Polo Ralph Lauren. Bracelets (on ankle, from top), $175 and $195, by Chan Luu.
Opting for relaxed, striped shirts that evoke a vintage sensibility offers both comfort and a touch of retro flair. Layering swim trunks beneath looser-fit shorts provides a functional and stylish solution for varied activities.
Subtle yet stylish accessories like anklets add a personal touch, while versatile sneakers from Village PM ensure comfort for exploration. These choices underscore a practical yet refined aesthetic suitable for dynamic travel itineraries.
Louis Vuitton
Striped Long-Sleeved Shirt
Louis Vuitton
18 East
Emery Pleated Big Shorts
18 East
Village PM
1.30PM
Village PM
The Executive’s Carry-On Checklist
O’Connor’s approach to travel grooming prioritizes efficiency and luxury. He packs only the essentials: a signature fragrance, a quality toothbrush and paste, and a high-performance face lotion with SPF.
Suitcase, $1,525, by Rimowa. Jacket, $1,280, by The Anthology. Pants, $665, by ERL. Shirt, $1,470, by Louis Vuitton Men’s. Underwear, $53, by Calvin Klein. Sunscreen, $18, by Vacation. Shirt, $1,100, by Celine. Jeans, $89, by Levi’s. Watch, $47,200, by Rolex. Tank top, $149, by Zimmerli. Sandals, $140, by Bedrock Sandals. Stylists’ own belt by Charvet. Shorts, $75, by Patagonia. Stylists’ own hat by Polo Ralph Lauren. Fragrance, passport, cameras, camera chain, and book, his own.
He insists on premium undergarments, favoring Calvin Klein trunks and Brooks Brothers boxers for their superior fit and comfort. His fragrance of choice, Etat Libre d’Orange’s Experimentum Crucis, is a conversation starter, consistently eliciting compliments.
Rimowa
Cabin
Rimowa
Celine
Short-sleeved Polo Sweater
Celine
Rolex
Oyster Perpetual 36
Rolex
Levi’s
Secondhand 501 Jeans
Levi’s
Richelieu
Tank Top
Zimmerli
Bedrock Sandals
Classic LT Sandals
Bedrock Sandals
Essential for any trip are versatile shorts like Patagonia’s Baggies, suitable for hiking, swimming, or casual wear. His choice of a vintage-inspired Ferrari cap adds a distinctive, retro touch, completing his travel-ready look.
Vacation
Classic Face Lotion SPF 45
Vacation
Calvin Klein
Icon Cotton Stretch 3-Pack Low Rise Trunk
Calvin Klein
Brooks Brothers
Cotton Broadcloth Plaid Boxers
Brooks Brothers
His travel bag, a Rimowa carry-on, is meticulously organized, holding essentials like a The Anthology jacket, Louis Vuitton shirt, and a distinguished Rolex watch, signifying a commitment to quality and style even on the move.
Transitional Dressing for the Modern Executive
The art of transitional dressing is crucial for navigating varied summer environments, from client meetings to relaxed excursions. O’Connor demonstrates how to master this with versatile pieces that maintain a polished appearance.
Patagonia
Baggies Shorts – 5"
Patagonia
A knit polo, offering a more refined silhouette than a standard t-shirt, is perfect for both client interactions and evening engagements. Separating pieces from a linen suit, such as the trousers, allows for maximum versatility, pairing easily with other items for varied looks.
Shirt, $1,520, by Versace. Pants, $425, by The Anthology. Bag, $750, by Tory Burch. Towel (in bag), $810, by Hermès.
A flexible raffia bag provides ample storage without adding bulk, perfect for carrying daily essentials. These carefully selected items ensure a sophisticated presence, adapting effortlessly to any occasion.
Versace
Mouliné Jacquard Knit Polo
Versace
The Anthology
Sueded Linen Suit Jacket
The Anthology
The Anthology
Sueded Linen Pleated Trousers
The Anthology
Shirt, $1,080, by ERL. Jeans, $1,950, by Dior.
PRODUCTION CREDITS:
Photographed by Bowen Fernie
Styled by Haley Gilbreath and Avidan Grossman
Grooming by Kumi Craig at The Wall Group
Tailoring by Ksenia Golub
Prop Styling by Fitz Fitzgerald
Business Style Takeaway: Mastering efficient packing and versatile styling, as demonstrated by O’Connor, projects an image of competence and sophistication. This attention to detail in personal presentation, even during travel, subtly reinforces an executive’s brand as organized, discerning, and always prepared.
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