It’s that time of year again! Though, frankly, I’m more excited about surrounding myself with mountains of chocolate than thinking of ways to splurge on my sweetheart and, oh, to dress for the occasion.

Though many people say Valentine’s Day is overrated, I won’t judge you for stressing out over the choice of outfits – because I feel the same! These days, the chilly air is keeping me all bundled up, which makes it even harder to pick a cute, foolproof, failsafe and appropriate outfit.

When it comes to dressing for a date, there are always so many rules floating around. But the cliché is true – it all boils down to picking what makes you feel best. Here are some handpicked pieces suitable for almost any cold-weather date scenario.

1. Monochrome Dress from Koo

While it’s advisable to look a little more polished, I’d go for this fuss-free long-sleeved dress, cast in an understated black-and-white print all over, and wear a popping lipstick to dress it up.


2. Sweater Dress with Shoulder Cutouts from chuu

Bravo for having the confidence to show off some skin, but given the chilly temps these days, going all off-shoulder might not be very practical. This relaxed sweater with cutouts at the shoulder exudes comfy chic and shows just the right amount of skin. If I’m feeling sexy, I might pair this with a tight skirt and bright heels.


3. Sweater Dress from Babi n Pumkin

A slightly draped sweater dress is a lovely and practical choice for almost any winter date – it creates a low-profile look while still accentuating some curves. Think about how ridiculous it is to freeze your butt off in a short dress and heels – you’d treasure this comfortable dress even more! I’d pair this creamy-hued option with black leggings.


4. Cowl Neck Sweater from LIPHOP

Loved for the same reasons as the above sweater dress, this cowl-neck sweater is a great choice if you’re looking to show a hint of skin. Just pull the cowl neck down a little. I’d say the style is especially great for casual dates.


5. Long-Sleeved Skater Dress from Camellia

I enjoy showing some curves when feeling up to it. But if it’s a feast filled with sumptuous food, I’d go for a more forgiving silhouette. This dress is simple, sweet and a great option for a first date. Its cinched waist will give you some shape while the flowing skirt provides just enough room to breathe.


6. Belted Wrap Coat from CHERRYKOKO

You can keep warm and look alluring with awesome outwear like a classy coat. I am digging the Olivia Pope style (Isn’t everyone?), hence this sassy wrap-style coat with a matching waist sash for a feminine fit. Not only does it keep you warm – it looks fashionable too.


7. High-Waist Skirt from Attrangs

A cropped knit top with a tailored high-waist skirt like this one looks hot but fuss-free. It’d go perfectly with the coat from #6!


8. Stretchy Faux Leather Pants from SHOPGIRLS

If you want to keep the body heat in while still showing your curves, these faux leather skinny pants would be a great choice. The pants create a warm and decent look when paired with the perfect dress.


9. Riding Boots from migunstyle

I just love the skinny pants and riding boots combo – it is my favorite go-to for winter and works for every occasion. The minimal embellishment and sleek gold-tone buckle on this pair ooze a lovely mix of preppy and smart.


10. Pointed Flats from Picapica

It’s more comfortable to walk in flats – the style makes it easier for me to relax and just be myself, which is what’s really important. Plus you can’t go wrong with nude shoes – they never overwhelm and match well with everything!