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Picking date night outfits can be tough whether it’s your first date or your 25th. The perfect outfit needs to be flattering and comfortable, plus it shows off your personal style. To cut down on outfit changes, polling your friends and last-minute shopping sprees, we’ve teamed up with the guys from StyleLikeOurs.com and put together five perfect date night outfits to wear this winter.

50 Shades of Grey

grey stylish jumper - the clothes maidenSource // Grey Embellished Jumper

Yep, you better believe it’s freezing cold outside – and if you’re a girl who hates to be cold, then wrap up warm in a pair of high waisted skinny jeans and a cosy grey knit. Because this is date night, feel free to go for a jumper with some fancy details on it, from cutesy embellishments to a studded collar.

Boho Vibes

bohemian red dress - the clothes maidenSource // Red Knitted Swing Dress

You can’t ever go wrong with a bohemian inspired swing dress. To finish the look off, team this dress with a pair of ankle boots and a felt hat. The perfect combination to stand out from the crowd, instead of blending in. Your other half will definitely be impressed.

Dogtooth Texture

date night outfits - the clothes maidenSource // Dogtooth Blazer

If you have an evening date planned, then we recommend you dress appropriately – such as adding a stylish dogtooth wrap to your outfit. Not only with this style look good, it’ll keep you nice and warm for when you step outside of the cinema or restaurant.

Keeping it Casual

casual date outfit - the clothes maidenSource // Snake Print Trousers

If you have a casual date arranged, but still want to look as though you’ve made a real effort – then you can’t go wrong with a pair of chic snake print trousers. Team them with a pair of loafers, a knit and a duster jacket and you’re on your way to looking like a million dollars!

Effortlessly Chic

chic fashion blogger outfit - the clothes maidenSource // Black Skort

A skirt is a smart solution for adding an instant chicness to your style. A skort is a timeless piece of clothing, what looks great, smart and stylish, you can’t beat this cut. Complete the look with a black fur coat, a ribbed jumper and don’t forget to wear a pair of tights! You don’t want your pins to freeze off!

Avery Parker