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Whether you’re exploring the cobblestone streets of Paris, the vibrant neighborhoods of New York, or the historic charm of Prague, a long weekend city break is always a great idea. But I always struggle packing for a weekend away, especially if I don’t have a checked bag. I want to look chic without overpacking or being charged extra baggage fees. My solution? A capsule wardrobe that’s versatile, stylish, and fits snugly into a carry-on.
So, I’ve pulled together the perfect weekend trip packing list of just 14 pieces of clothing, to create 7 outfits for every occasion on your weekend away. I’ve also linked my favourite items below, but of course you can work with items you already have. The key with this packing list? Keep the colours neutral and you’ll have an infinite number of outfits!
Your 14-Piece Packing List:
- 2x T-Shirts (one white, one black)
- Dressy Top (something that can transition from day to night)
- Dressy/Flowy Trousers (think light fabric, perfect for day and night)
- Dress (classic little black dress is perfect)
- Long Denim Skirt (versatile and trendy)
- Leggings (comfy yet stylish, ideal for travel days)
- Sweatpants (for ultimate comfort without sacrificing style)
- Blazer (adds a polished touch to any outfit)
- Hoodie (cozy and casual for layering)
- Bomber Jacket (edgy and cool, perfect for those in-between weather days)
- Heels (a must for those nights out)
- Converse (classic and comfy—I also love the platform ones for an elevated look!)
- Crossbody Bag (black usually goes with everything!)
Keep reading to see how you can use these 14 items to create your 7 outfits and the perfect city break packing list.
Day 1: Travel Chic & Effortlessly Cool
Day Outfit: White T-Shirt + Sweatpants + Bomber Jacket + Converse
As you embark on your journey, you’ll want to be as comfortable as possible. The white T-shirt paired with sweatpants gives you a relaxed and easy-to-move-in outfit. Throw on the bomber jacket for warmth, especially if the weather is chilly or if you’re dealing with unpredictable airplane temperatures. Converse will keep your feet comfortable during transit, and a crossbody bag ensures your essentials are easily accessible.
Evening Outfit: Dressy Top + Long Denim Skirt + Heels + Blazer
After settling into your accommodation, you might want to head out for a casual dinner or a stroll around the neighbourhood. Transition to your dressier top and pair it with the long denim skirt for a chic, effortless look. The bomber jacket adds a cool edge and warmth, perfect for an evening out. Swap the Converse for heels, and your crossbody bag is ideal for keeping your hands free while you explore your new surroundings.
Day 2: Elegant Urban Explorer
Day Outfit: Black T-Shirt + Long Flowy Trousers + Bomber Jacket + Converse
For a full day of sightseeing, you’ll want an outfit that’s comfortable enough for walking but stylish enough for all those photo opportunities. The black T-shirt tucked into your long flowing trousers gives you a trendy yet practical look. Layer the bomber jacket for those crisp autumn mornings. Converse are again the best choice for walking around the city.
Evening Outfit: Dressy Top + Dressy/Flowy Trousers + Heels + Blazer
After a day of exploring, it’s time to dress up a bit for dinner or drinks. Swap your T-shirt for the dressy top – this combination is both chic and comfortable. The blazer adds a polished touch, making the outfit perfect for a more upscale restaurant or a night at the theatre. Slip on your heels to elevate the look, and keep your crossbody bag.
Day 3: Laid-Back Brunch and Late Nights
Day Outfit: White T-Shirt + Long Denim Skirt + Bomber Jacket + Converse
For your third day, whether you’re visiting museums or relaxing in a café, you’ll want a look that balances style and comfort. Pair the white T-shirt with the long denim skirt for a casual yet put-together outfit. The bomber jacket keeps things relaxed and is ideal for the fluctuating temperatures you might encounter indoors and out. Converse shoes keep you comfortable during those long strolls.
Evening Outfit: Dress + Heels + Blazer
On your final evening, pull out all the stops with the classic little black dress (LBD). This piece is a go-to for any stylish night out. Pair it with the blazer to add structure and warmth. The heels will complete your sophisticated look, perfect for a fancy dinner or catching a show.
Day 4: Travel Home in Style
Outfit: Leggings + Hoodie + Blazer + Converse
As your trip comes to an end, you’ll want to travel home in comfort. The hoodie paired with leggings offers ultimate relaxation without sacrificing style. Layer on the blazer for extra warmth and cosiness, especially if you’re catching an early flight or train.
And there you have it—7 stylish outfits from just 14 pieces of clothing! By mixing and matching these essentials, you can create a versatile wardrobe that’s perfect for any city break. So, next time you’re packing for a long weekend, keep it simple, keep it chic, and enjoy the adventure!
