Walking dates are gaining in popularity, whether it’s a local walk around the park with a friend and a coffee or a trip to the countryside with your partner for a day-long hike. It’s an inexpensive way to catch up with someone, get some fresh air and exercise.
However, it's important to make sure you're wearing the right gear for performance and comfort. So, we've compiled what to wear on a countryside walk date, meaning there's zero guesswork necessary for the occasion.
What to Wear on a First Walking Date
A Waterproof Jacket for Ladies
Even if you think the weather is going to be beautiful, there is always a chance that it will rain at some point in the UK. So, taking a waterproof jacket is a smart idea.
- A jacket in a packet - This should be your go-to on warmer days. They basically do what they say on the tin: they fold up into a small bag, which takes up minimal room in a backpack! You can go for a neutral shade, such as grey or navy or go bold in red, bright blue or purple.
- An overhead smock - Sometimes, light rain can hang in the air all day, but that doesn’t mean you have to hide indoors. An overhead waterproof smock is a great option for fine droplets and is an easy jacket to layer when you need extra warmth. With three large pockets on the front and an oversized hood, it's as practical as it is stylish.
- A ¾ length raincoat - If you’re expecting a heavier forecast, you might want a longer length coat for a walking date. The mid-thigh length is flattering on all figures and is long enough without feeling restrictive. It’s lightweight enough for warmer days, but again, you can always layer a fleece underneath if the temperature drops.
- A bomber jacket - The ultimate cool girl item has to be the bomber jacket. The oversized look is very on-trend but still waterproof and super practical. Our Ripon style comes in a myriad of colours, so you can go for your favourite bright colour or opt for a neutral to go with your entire wardrobe.
A Waterproof Jacket for Men
- A walking jacket - Men love practical clothing items and a walking jacket is perfect. We’ve revamped our bestseller with newer colours but with all its original features: stormproof cuffs, soft lining, lots of pockets, a foldaway hood and so much more.
- A bomber jacket - If the weather is cool with light rain, a bomber jacket is a great option for a walking date. It’s one of our most practical jackets too, with plenty of pockets and a fold-in hood. With a line-up of wearable neutral tones to choose from, it's designed to complement your existing country wardrobe.
- A pack and go jacket - How often do you leave the house without a jacket when you really need one? Our pack-and-go style is perfect for unexpected weather. Stick it in your backpack for hikes or leave it in your car for city centre walks.
- A hiking jacket - For longer walks in the cold, you'll need something thicker. Our hiking jackets are designed to be fully waterproof for maximum practicality, and have clever seams to lock in warmth even in gale-force winds.
Sturdy walking boots for Ladies
Again, it doesn’t matter what time of year you go on a walking date, you'll always need sturdy, practical, comfortable footwear. Whether you opt for trainers or boots is up to you, but they must have a good tread and be comfortable enough to wear for hours at a time. Of course, we’re talking about countryside walks here so it will depend on your location as to whether you can get away with a softer shoe.
Women are often put off by walking boots as they’re not the most stylish type of footwear around. However, if you go for walks often or just generally spend a lot of time outdoors, walking boots are a must. They offer that extra support around the ankle, heel and ball of the foot that regular shoes don’t.
Sturdy Walking Boots for Men
An essential for any country gentleman, our leather walking boots are designed to protect your feet and ankles and are made to last. They can take a few wears to break in properly, so make sure to wear them around the house a handful of times before your walking date.
Want to know who’s clocked up some serious miles in their boots? Meet some of the famous walkers who’ve turned their love of the outdoors into incredible adventures.
A Rucksack
You can’t go on an outdoor excursion without a bag to carry your extra gear in. A rucksack is the easiest bag to take with you. It spreads the weight on your back and shoulders and leaves you hands-free to take on uneven terrain. If you’ll be out for the day and carrying lunch/dinner around, our 20l rucksack is the better option for you. Try to only take the essentials because whilst these rucksacks can take a lot of weight, your back won’t be able to after a couple of hours!
For shorter walks where you still need a few essentials, our pack-and-go style is ideal. It’s perfect for storing a couple of drinks, snacks and a pack and go jacket. Its 25l storage is much bigger than you might think so you could even store a blanket in for a picnic halfway through your walking date!
Walking Date Outfit Ideas for Each Season
Spring/summer
To make an outfit, consider the below items for spring and summer walking dates. You need to stay cool but don’t forget about sun protection for your skin, eyes and head! Even on cloudy days, UV rays can still get to your skin so always pop some suncream on every few hours. Here are a couple of items that you can consider for warmer days.
- A cotton T-shirt or vest - You’ll need something that wicks the sweat so stick to cotton T-shirts and sportswear.
- Loose-fitting shorts - You might want to cover your legs if in woodlands or if you’re prone to heat rash or bites. For most of us, shorts are a great option for warmer weather.
- A baseball cap - You need to keep your head from getting too hot!
- Sunglasses - Protect your eyes from the sunlight and look super cool at the same time? What’s not to love?
Autumn/winter
Autumn and winter walking date outfits require a bit more preparation as often you have to pack extra layers, just in case the temperature dips even further. It’s never a bad thing to be too prepared! Here are a handful of pieces that we always grab before a cold weather walk.
- A base layer top - Thermals are the ideal base layer top but you could opt for a cotton T-shirt instead.
- A fleece mid layer - Fleeces are great for layering as they tend to be thin but still full of warmth. You can always pop it in your rucksack if it gets too warm.
- Thermal leggings (if it gets particularly cold) - People who get cold often swear by thermal leggings so if it’s freezing outside, you might want to consider wearing a pair under your trousers!
- Stretchy trousers - You need to be able to move freely so walking trousers are the best option. However, any trousers that are fitted and stretchy are just as good. Try not to wear any denim jeans or skinny jeans though as they’re not always very comfortable.
- A woolly hat, a scarf and gloves - Haven’t you heard that heat escapes from your head and hands? Cover them up and add a scarf if it’s freezing too. Bonus points if they all match!
FAQs About Walking Clothes for Women & Men
What shoes are best for a walking date?
Go for comfortable, supportive shoes like trainers or casual boots. Make sure they’re clean and in good condition.
Should I dress casual or smart for a walking date?
Aim for smart-casual. Think neat jeans or chinos with a nice top or shirt – relaxed but still put together.
What should I avoid wearing on a walking date?
Skip anything too formal, overly sporty, or uncomfortable. Heels, stiff shoes, and clothes you can’t move in are best left at home.
How can I stay comfortable but stylish on a walking date?
Layer up with well-fitted casual pieces, add a jacket or knit for polish, and keep accessories simple.
Walking dates are inexpensive when you’ve got your outfit sorted. Take your own snacks or meals, don’t forget your refillable water bottle and spend the day in the great outdoors. Take your partner, friend, parents, family, friends or just yourself and soak up some vitamin D!