I’ve always thought February gets a bad reputation. Yes, it’s grey and cold and everyone’s abandoned their New Year resolutions, but it also brings the perfect excuse to whisk yourself away somewhere lovely. My partner and I have made it a bit of a tradition now to plan something for Valentine’s week, and honestly, I spend far too long thinking about what to pack.
This year, I’m completely obsessed with that retro travel romance aesthetic. You know the look I mean. Think Grace Kelly boarding a plane in the 1950s or Brigitte Bardot lounging on a yacht. There’s a reason those images still capture our imagination decades later.
So, wherever you’re headed this February, here’s how I’d approach getting dressed.
Beach Escapes: Floral Maxi Dresses and Jumpsuits
For beach holidays, I always reach for floral maxi dresses first. They’re forgiving after a big lunch, they look gorgeous billowing in the sea breeze, and they photograph incredibly well. I’d suggest hunting for styles with defined waists rather than completely shapeless ones. A cinched middle gives you that lovely hourglass silhouette while the flowing skirt does all the hard work of keeping you cool.
Colour-wise, I’m drawn to coral tones, pinks, greens and blues this season. They complement sun-kissed skin beautifully and feel inherently romantic without being too saccharine.
Jumpsuits are my backup option when I want something slightly more practical. Last year I found this wide-leg number covered in tropical leaves, and I wore it approximately seven times in ten days. No regrets. The beauty of a jumpsuit is that you look pulled together with zero effort. Chuck on some gold hoops, slide your feet into woven sandals, and you’re sorted from morning coffee through to evening cocktails.
City Breaks: Pencil Dresses and Skirts
European cities demand a bit more thought, don’t they? You want to look smart enough for that restaurant you’ve booked but comfortable enough to wander for hours without developing blisters or a bad mood.
I absolutely love pencil dresses for city breaks. There’s something about that fitted silhouette that makes you stand taller and feel more confident. I’d steer towards rich colours like burgundy, black, teal, or midnight blue, These tones feel special and they look fantastic in photos against old architecture.
If you prefer separates, a well-cut pencil skirt paired with a silk blouse gives you more outfit options from fewer pieces. I’m particularly fond of high-waisted skirts in heritage patterns like houndstooth or subtle checks. They have that lovely vintage feel. Add a blouse with interesting details at the collar and you’ve got an outfit that works for galleries during the day and candlelit dinners later on.
Do bring a cropped jacket or blazer. Evenings can turn chilly quickly, and nothing ruins a romantic stroll quite like shivering.
Countryside Stays: Swing Dresses and Swing Skirts
This is my favourite kind of getaway, if I’m honest. A cosy pub with rooms, long walks through muddy fields, coming back to a roaring fire. Absolute bliss.
Your clothes should be warm and practical but still make you feel pretty. Swing dresses are perfect for this. The relaxed fit means you can enjoy a full Sunday roast without any discomfort, but the feminine shape keeps things from veering into frumpy territory.
I’d suggest warmer colours for the countryside. Sky blue, rust, lilac, rich burgundy. These tones look gorgeous against bare trees and grey skies. Layer with chunky cardigans and add woolly tights when the temperature drops. Ankle boots are essential.
Swing skirts work equally well if you prefer separates. A flared midi in corduroy paired with a cosy roll-neck jumper is my go-to walking outfit. Then I’ll swap the jumper for something slightly smarter when we head to dinner. Packing becomes much easier when you plan these little switches in advance.
Staycations: Shorts, Blouses, Pullovers, and Jeans
Staying home together can be just as romantic as going anywhere, and I refuse to spend the whole time in tracksuit bottoms. Well, maybe some of the time.
For pottering about and popping out for brunch, I love tailored shorts with a pretty blouse. It sounds summery but it works in February if you add thick tights and a chunky pullover on top. The key is choosing pieces that feel intentional rather than grabbing whatever’s nearest.
Good jeans are your friend here too. A pair that fits properly, worn with a crisp shirt or a nice knit, looks effortlessly put together for anything from farmers’ markets to cooking dinner at home. I think the secret to staycation dressing is simply avoiding your default loungewear. Save that for actual lounging. When you’re doing something together, even if it’s just making pancakes, wear something that makes you feel good.
Road Trips: Retro Trousers and A-Line Dresses
I find road trips incredibly romantic. No fixed schedule, just following wherever the road goes, stopping when something catches your eye.
The challenge is looking decent after hours crammed in a car. Creased clothes and a grumpy face aren’t the vibe we’re after.
High-waisted retro trousers are brilliant for this. Wide legs in cream, camel, pastels or navy worn with tucked-in tops look fantastic at every pit stop. Stripes are my weakness here. They feel so perfectly suited to adventures.
A-line dresses are another winner because the shape doesn’t crease badly and they’re comfortable for long journeys. Choose a midi length in a vintage-inspired print, something with small florals or geometric patterns, and pair with comfortable sandals or flat boots. You’ll look like you’ve stepped out of a 1960s road movie, which is precisely the point.
Whatever your February plans look like, I hope you dress in a way that makes you feel wonderful. Sometimes the right outfit turns an ordinary trip into something that feels like a proper adventure.
