I caught it again last week. He’s got a perfectly good outfit on — clean tee, well-fitted trousers, the whole thing thought through — and then he slings a battered old backpack over his shoulder before we head out. The bag undoes everything. An outfit is only as good as its least styled part, and honestly? Most guys don’t even realize.
So I did what I do: I made notes. Not a gift list, just the bag styles that actually get used, organized by the life you’re living — weekend trips, the office, a day at the beach, or a flight somewhere. I’m a closet person by nature, but summer travel made me study bags like they’re wardrobe staples. Because that’s what they are.
1. The leather holdall: the buy-once piece
A proper leather holdall is one of those rare things that gets better with age. The more you use it, the more character it picks up, and if you buy it well and look after it, it can outlast you. It’s timeless, it reads grown-up, and it goes with everything.
It’s the bag for a weekend away, a work trip, or even just a gym session before the office. Size-wise, you want enough room for a change of clothes, a change of shoes, a wash bag, and your extras. A laptop compartment and a few zip pockets for valuables make it a keeper.
Here’s the honest part: leather luggage is expensive, and I know that’s a real consideration when you’re budgeting. But think of it as the investment piece — you pay up front, and you spend less for years. If that’s the path you want to take, names worth looking at: Luca Faloni, Velasca, Mismo, and Bennett Winch.
2. The elevated tote
You don’t need a big bag for a day at the beach, an afternoon in the park, or wandering between a café and a bar. Nine times out of ten, a simple tote does the job. The free canvas one from the record store? Fine for carrying books. But for the rest of summer, you can do better.
Spend a little more and you get something durable that actually works as part of the outfit instead of just a tool for a job. I’m a fan of a nice nylon tote with a bit of color — the slightly oversized kind that’ll hold a beach towel without looking stuffed. Adsum, Battenwear, and Arket all have options that fit the bill, and ELLIKER, Klättermusen, Montbell, and Mismo are worth a look too.
3. The wash bag
Okay, I’ll be blunt: if your electric toothbrush, contacts, and aftershave are living in a plastic sandwich bag, we need to talk. It’s not exactly a polished look — and it’s completely avoidable with a real wash bag.
One that’s the right size fits all your toiletries, so you can drop it into your main bag without toothpaste staining your shirt or the sole of a shoe meeting your toothbrush head. Go fancy with a little leather number — Velasca, Dunhill, and Smythson do this well — or keep it casual with canvas from Porter-Yoshida & Co., Topo Designs, and Sunspel.
4. A proper suitcase
Suitcases are expensive, but if you travel a lot, they’re worth splurging on. A top-tier case makes packing easier, airport transit less stressful, and gives you real peace of mind when you hand your stuff to baggage handlers who handle things… with enthusiasm.
You have two routes: the classic leather route, like Globe-Trotter or Louis Vuitton, or the modern hard case. In my opinion the hard case is the smarter pick, and Rimowa is the best brand in the business. The catch: prices tend to run well over $1,200 (that’s the £1,000 mark the original pricing sits at). On a tighter budget, Carl Friedrik and Floyd are the ones to check out.
5. The suit carrier
Ever tried traveling with a suit? It’s almost impossible to arrive anywhere without it looking like a crumpled mess. And if you’re straight off the flight and into a meeting, you don’t have time to fix it.
Prevention beats repair, so the fix is a purpose-made suit carrier. Not the one the dry cleaners gave you — a piece of luggage that looks the part and carries your other things too. A good one lets you transport tailoring without creasing it: some fold in half and clip together, others wrap around a holdall, and the best have zip pockets for accessories. Bennett Winch makes some of my favorites in this category, and Mismo, BRICS Life, and Hawes and Curtis are solid alternatives.
6. The nylon messenger
Messenger bags are super practical, but they can look a bit boring. The trick is to go for a slouchy nylon one that’s less structured and more relaxed — that’s what keeps it looking current.
This is the office bag. It’s comfortable to carry, easy to swing out of the way on a packed train, and handy to unzip on the fly without taking it off. It’s also great for summer because it leaves your back free to breathe. Solid options: COS, Snow Peak, Porter-Yoshida & Co., ARCS, and Carhartt WIP.
7. The folio
If all you’re carrying is a few documents, a backpack or messenger is overkill. That’s what a folio is for — basically a large leather envelope, just the right size for some A4 documents and maybe an iPad. You carry it under your arm and call it a day.
Folios are especially good in warm weather when you’re heading to the office and don’t want a bag making you sweaty and creasing your shirt. They look sharp, too. Carl Friedrik, MR P., Mismo, Smythson, and Bennett Winch all make ones worth considering.
8. The outdoorsy backpack
Heading into the hills this summer? A flimsy everyday backpack won’t cut it if you’re walking further than a couple of miles. If the plan is to actually get out into nature, you need something comfier, bigger, more breathable, and more supportive.
A proper hiking pack carries extra layers, lunch, water, and everything else the trail throws at you. Look for a padded back, and if you can find one with a mesh backplate for ventilation, even better. Osprey, Arc’teryx, The North Face, and Patagonia all have plenty of options that are practical without sacrificing style.
9. The crossbody bag
Sometimes a full-size bag is overkill. All you need is room for keys, wallet, phone, and maybe sunglasses. That’s the crossbody — the perfect small-scale summer carry.
A compact sling worn across the body keeps your essentials close without weighing you down or making your back sweat. It’s ideal for city breaks, dog walks, festivals, or days when you’re just hopping between coffee shops with a paperback and your AirPods. Look for lightweight technical fabrics, weatherproof zips, and a few compartments for easy organization. And wear it confidently — this is a functional, fashion-forward move, not a throwback to 2005 waistpacks. Mismo, Klättermusen, Stone Island, and Carhartt WIP all make good ones.
Quick FAQ
Do I really need nine different bags? No — pick the three that match how you actually spend your weekends and workdays. Most people need one carry bag for trips, one everyday bag, and one small bag. The rest is upgrade territory.
Where do I start on a budget? Start with the elevated tote and the crossbody. Both are the most-used, most-visible, and most affordable categories here — and they do the most for how your outfit reads.
Is the expensive leather holdall actually worth it? Only if you’ll use it often enough to let it develop. It’s an investment piece, not a weekend purchase — if trips are a couple of times a year, save your money for a good hard-shell case instead.
One more thing: I don’t own most of these — my boyfriend does. Which is exactly how I got the data. He’s been walking around New York with a different bag for three weeks straight, and I’ve watched which ones get used and which ones sit in the closet. That’s all this list really is: field notes.
Related reads: capsule wardrobe essentials and my guide to budget finds that don’t look cheap.
