Failsafe date outfits

It’s hard to advise on date wear without sounding like a 1950s etiquette guide. Of course, men aren’t difficult to dress for. Broadly speaking, their ideal girl wears tight jeans and white vests by day, and little black dresses by night.

But unless you live in a rom-com, your own wardrobe is probably a little more fashion forward. And that’s where the dilemmas start. Yes, a date is a sales pitch of sorts and, yes, you want to please. But if that means masking the real you, you’re asking for trouble down the line.

[See also: 5 ways to tell if you fancy him]


So, here are three man magnet looks, one of which can be adapted to showcase you to best advantage jewellery and accessories add individuality to generic date clothes. Make up should be radiant but appear minimal (‘appear’ being the operative word). After that, it’s down to you.

Jeans, heels and top

Elizabeth hurley and Janina Gavankar illustrate the casual combination.
Elizabeth hurley and Janina Gavankar illustrate the casual combination.


Men love this rather yawn-making combo. You can’t go wrong with jeans, especially with wiggly-walk heels, and happily, they never look like you’ve tried too hard. If you’re so inclined denim also provides some ballast for an edgier top. Or, if you really are a pH 5.5 girl next door, jeans are perfect with a pretty camisole and cardie. He’s already imagining you two chatting over the muesli.

Pencil skirt

Christina Ricci and Myleene Klass create curves wearing pencil skirts.
Christina Ricci and Myleene Klass create curves wearing pencil skirts.


Part of date-dressing is flagging up your assets (or should that be ass-ets). So, if you can pull off a pencil skirt, do it. It’s no less sexy than a mini, but never looks desperate or like mutton. This look works best if your date follows a day at the office. Cue sexy secretary fantasies.

Killer dress

Kelly Brook and Blake Lively wear figure flattering dresses.
Kelly Brook and Blake Lively wear figure flattering dresses.


Weirdly, men respond best to clothes they can describe in one sentence, e.g. ‘She was wearing this little red dress’, not, ‘She was wearing these peg leg trousers, with layered jersey vests, a cropped cape and a floaty scarf. Dresses should strike the right balance between demure and figure hugging. Neat little shifts are good, as are translucent wispy things (all men have sheer goggles). Careful though.
Discerning dudes can interpret frocks as mumsy. If in doubt team with heels and high drama jewellery.

A must to avoid:
Sadly, some of the best clothes are universal man repellents. Wait until you’ve been together for six months, before breaking out any of the following:

  • Directional tailoring

That super structured, practically square, dove grey dress you picked up in COS? The one that completely obscures your figure? Unless he’s an architect, or gay, he’s going to hate it. Just saying.

  • Empire line smock dresses

These make men think of pregnancy.

  • Playsuits

Short playsuits ones can indeed be creepily kiddie-like. The long ones are just plain mad in male eyes – probably because they look like they take ages to take off. They also double the size of anyone’s bum.
Ditto, harem pants and culottes.

  • Long A-line skirts

Hippie chic tends to go down badly with lowest common denominator men.
If your art teacher could have worn it, leave it in the wardrobe.

  • Out there cleavage

They have a point here. For once, men and the catwalk are in agreement.

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