Packing the right sneakers can make or break a trip, especially when your days swing from airport marathons to spontaneous city wanders. We road tested Vans and Converse side by side so you know exactly what is worth space in your carry on. The winners deliver comfort, grip, and outfits that look pulled together without trying. Here are six pairs that will keep you moving and still look good in photos.
Vans Old Skool Sneakers
The Vans Old Skool shines when you want one sneaker that does almost everything. The rubber waffle sole grabs slick subway steps and rainy sidewalks, so you feel planted even with a backpack on. Cushioning is moderate, but it spreads impact across the foot nicely for terminal dashes and museum loops.
Styling is painless because the silhouette reads classic without trying too hard. Dark jeans, a breezy dress, or tech pants all lock in with the Old Skool stripe and low profile. You will appreciate how the suede and canvas age gracefully, picking up character instead of looking tired.
For travel days, the shoe balances comfort and structure so your feet do not feel sloppy after hours of wear. It is not a plush runner, yet it holds up through long city days better than expected. If you only pack one pair, this is the go to that covers flights, coffee runs, and casual dinners.
Vans Sk8-Hi High Top Sneakers
If you like a bit more support, the Vans Sk8-Hi adds ankle coverage without losing the laid back vibe. The padded collar helps stabilize when sidewalks tilt or when you zigzag with luggage. The waffle sole again is the hero, keeping traction on wet crosswalk paint and smooth airport floors.
These skew slightly heavier than low tops, but the tradeoff is welcome on long walking days. The high top frame hugs the heel so your foot does not slide on downhill blocks. You feel comfortably locked in while still maintaining that street friendly look.
Styling leans toward jeans, cargos, or leggings tucked into the collar for a clean line. In cooler climates, the extra coverage keeps ankles warmer during early morning departures. When your itinerary mixes sightseeing and casual nights out, the Sk8-Hi brings stability and style in one carry.
Vans Classic Slip-On Sneakers
When you want zero fuss, the Vans Classic Slip-On is the airport hero. Slide in and out at security with one hand while the line keeps moving. The shoe is light, breathable, and easy to pack, so it disappears in your bag and reappears ready for a stroll.
Grip is solid for a slip-on thanks to the waffle outsole, making quick pivots with luggage feel secure. Cushioning is modest, so plan it for short to medium days or pair with supportive insoles. The low profile keeps outfits simple and unfussy, which is perfect when you are hopping between trains.
For weekend getaways or carry on only trips, this is the throw-and-go option that earns its keep. It pairs with shorts, dresses, and joggers without a second thought. If comfort and convenience are priorities at the gate, you will reach for these first.
Converse Chuck Taylor All Star Low Top
The Chuck Taylor Low Top is the icon you can match with almost anything. Lightweight canvas keeps your bag less bulky and your feet airy on warm days. The slim profile slides under wide leg pants or sits clean with cropped jeans for a timeless look.
Underfoot, cushioning is minimal, which you will notice on extra long walks. For city hopping and casual sightseeing, it is perfectly fine, especially with a thin insole. Traction is dependable on dry pavement, though it prefers fair weather over heavy rain.
What makes this pair great for travel is versatility and ease of styling. When outfits must multitask, the Chucks blend into daytime tours and low key dinners. Bring them when you want light, simple, and effortlessly cool without taking up space.
Converse Chuck Taylor All Star High Top
Take the classic Chuck formula and add ankle coverage for breezy or mixed weather days. The High Top shields against cool drafts on trains and late night strolls. It also gives a touch more stability around the ankle without adding much bulk.
Like the low version, cushioning runs minimal, so think moderate walking and frequent cafe breaks. The canvas breathes well, but it does not love heavy rain without a quick waterproof spray. Style wise, it pairs nicely with tapered pants or layered looks under a trench.
When the itinerary swings from museums to rooftop views, the High Top keeps outfits coherent and casual. It photographs well in travel shots thanks to that iconic patch. Pack it if you want classic energy with a practical nod to cooler climates.
Converse Chuck 70 Low Top Sneakers
The Chuck 70 Low Top levels up the classic with better padding and a sturdier build. You get a slightly thicker sole and a cushier insole that smooths out long museum laps. The premium canvas feels durable, which helps when trips stretch beyond a weekend.
While still not a running shoe, the added comfort is noticeable by late afternoon. The shoe has a touch more weight, yet it rides steady on urban terrain. If you value a vintage look with modern comfort, this is the sweet spot.
Styling is effortless, especially with neutral colorways that dress up better than standard Chucks. They transition from jeans to casual trousers without missing a beat. For full day travel where you want style plus staying power, the Chuck 70 earns a top slot.
