Every summer trip a professional woman takes this year is, in some sense, a working holiday. Some of that work is a single email before the pool opens. Some of it is a full client day squeezed between flights. The amount of work varies enormously — but the question of which bag to bring does not have to be complicated, if you start from the scenario rather than the suitcase.
This is a guide to choosing, organised the way real summer trips actually break down: by what kind of working holiday you are actually taking.
Start with the scenario, not the bag
Most bag-buying advice works backwards — here is a bag, here is who it is for. It is more useful to work forwards: here is the trip you are actually taking this summer, and here is what it demands of whatever you carry.
Four scenarios cover most of what “summer” means for the women VHL designs for. Each has a bag built around exactly that demand.
Scenario one: the city-to-coast handoff
A Friday flight out after a full work day, a weekend somewhere with water, a Sunday night flight back, Monday morning meeting unaffected. The bag needs to function as carry-on companion, beach-adjacent tote, and Monday-morning work bag again, often within 72 hours.
Best suited to: Jolene. Eight dedicated compartments, a trolley strap that rides on a carry-on case through the airport, and a padded compartment that fits a 16-inch laptop. It is built for the version of summer where the office and the coast are the same weekend.
Scenario two: the extended workation
One to three weeks, one destination, real work woven through most days. The bag needs to be light enough to carry comfortably every single day for the full length of the trip, and organised enough to survive being repacked each morning without becoming chaotic by day ten.
Best suited to: Ada. At 800 grams, it is the lightest of the New Work Bag line, built specifically for the days where the bag itself should never be the thing that makes you tired. A 16-inch laptop fit, structured compartments, and a silhouette that reads as easily on a café terrace as it does in front of a client on screen.
Scenario three: the high-intensity bleisure trip
A trip with a genuine business component — client meetings, a conference, back-to-back calls — bookended or interspersed with real leisure time. The bag needs to shift registers within the same day: structured and professional at 10am, relaxed and unremarkable at 8pm, without a wardrobe change of its own.
Best suited to: Amal. A 14-inch laptop compartment, a three-in-one design that moves between tote, crossbody, and shoulder carry, and an external phone pocket built for the day when the phone needs to be visible and accessible at all times. It is the bag for the trip that does not separate cleanly into “work days” and “off days.”
Scenario four: the everyday carry that just happens to travel well
Not every summer trip is a trip at all — some of it is simply the version of your regular week that happens to include more outdoor lunches, more last-minute plans, and slightly less predictable days. The bag needs to do what it always does, just somewhat more flexibly.
Best suited to: Potter, for the days that stay close to home but still demand a bag with real structure — sized for the essentials, without the bulk of a full travel bag, for the woman whose summer is busier than her holiday calendar suggests.
A quick way to decide
• Trip is under four days, mostly leisure, light work: Jolene
• Trip is one to three weeks, steady daily work: Ada
• Trip mixes real meetings with real downtime, same week: Amal
• Not really a trip — just a fuller-than-usual summer week: Potter
“I stopped asking which bag looks best for the trip. I started asking what the trip actually demands of it. The answer is almost always obvious once you ask it that way.”
Why one brand can answer all four
Most work-bag brands design for one moment: the commute, or the conference, or the carry-on. The New Work Bag line exists because the women VHL designs for do not live in one moment. The same person who needs Jolene for a weekend in Cinque Terre may need Ada for three weeks in Lisbon and Amal for a conference in Berlin that turns into a long weekend — sometimes all in the same summer.
That is the actual shape of a working holiday: not one trip, but a season of them, each asking something slightly different of the bag that has to keep up.
Final thought
A good summer bag does not ask you to choose between being on holiday and being reachable. It assumes, correctly, that you will be both — and it is built so that neither one suffers for it.
Shop Jolene → https://victoria-hyde.com/en/products/handtasche-jolene-in-orange
Shop Ada → https://victoria-hyde.com/en/products/ada-schwarz
Shop the New Work Bag collection → https://victoria-hyde.com/en/collections/women-new-work-bags
