Ready to wear: Dear Annie

If navy is my black (as in navy skirt or suit), what colour my legs? And shoes?

Greta, Wimbledon

It depends: on skirt length, shoe height and the exact shade of navy. If your skirt is short, your shoes flat, and the navy very dark then you can wear black opaque tights and shoes; or natural sheers and navy shoes. If your skirt is long and your shoes high then natural sheers will also be fine, with navy shoes. Navy opaques are also fine with navy flat shoes. The basic rule of thumb is that if you wear all navy then the navys should match up (ie be of similar deepness/lightness), which is rather hard to do. And although navy sheers can sometimes be okay, in general, natural sheers are best.

Being a bit thin on top, I find I need a hat in this cold weather. I have a nice red woolly one, knitted by my aunty, which I wear while walking. But I don't think it's quite right for work. What would you suggest?

Keith, Portsmouth

Well, what work could you possibly do that a red woolly hat would not be suitable for? I think it sounds splendid and anyway, you could always take it off just before you get to the office. Men are very bad at keeping warm, thinking it is unmanly, but given the choice between a nice, warm, glowy man and a shrivelled, cold one I know which I'd prefer.

I have hair that hangs lank. I achieve height and curl with an electric brush, then add lacquer to keep the style up. But any hat or headscarf, once on, depresses all the height and I emerge utterly flattened when I take it off. Any suggestions?

Mrs Le Cornu, Jersey

Well, nothing will keep your hair bouffed if you put something on it. It's like asking a souffle to stay souffled if you rest a dinner plate on it. I wish I could suggest some magic Annie trick but I can't. There are only two solutions: don't wear anything on your head, or adopt a flatter hairstyle.

I am a school teacher and feeling very upset at being made redundant and forced into early retirement. I am very interested in style and love my clothes. I hope to coach kids at home, but my tailored trousers and jacket and silk shirts do not seem appropriate. Some women look so good in jeans but I've never found they flatter me. I' m nearly 60, a size 14 with a bit of a tummy (not excessive) and I'm 5ft 51/2 in tall. Can you suggest a make of jeans or have you any other ideas?

Margot Lee, Harrow

I absolutely don't think you should wear jeans. Jeans suit some people, but as you've found they're not for you. Your tailored trousers, as long as they're not too tight, could easily be worn at home. Silk shirts can be worn outside the trousers for a more casual look. You sound in pretty good shape, so if you can spend a bit of money, this is what I suggest: Capri pants (to the ankle with a tiny slit) with straight hemmed shirts (ie not with shirt tails). Something in a linen mix would be nice, as this is a fairly stiff fabric and would not cling to the tummy area (as silk, I have to say, would). Flat pumps or loafers would be comfortable and ideal (you could also try ballet pumps, that cost around pounds 10, as they are divinely comfortable). A nice scarf around the neck would also be good, I think. You can pick these things up anywhere, but places such as Jaeger do particularly stylish pieces.

I'm in a spot of bother. I cannot think what would be a suitable item of clothing to buy my girlfriend for Valentine's Day. I don't want to be cliched and buy lingerie but instead would like to buy her something that is rather special and classic. Anything with understated elegance would be perfect. It doesn't have to be a whole outfit, but perhaps an accessory?

PS: I have a small worry concerning cufflinks. Does one wear silk cufflinks only for evening dress and heavy cufflinks for only daywear, or does it not matter?

J, Maidstone

Well lingerie is cliched, but it is lovely to receive. Where men invariably go wrong is buying something in red and black (or all red) and few women would chose to wear scarlet underwear. You can buy something from La Perla (the Rolls-Royce of underwear) that is luxurious and she might never buy herself. Also avoid "fantasy" underwear that men buy for their women to wear but which is usually for themselves (if you see what I mean). Of course there are some girls who like wearing scratchy lace crotchless panties, or cut out bras, but they are in the minority. What about something from Prada (their shop is in London's Sloane Street)?

A purse, bag, or pair of shoes would certainly be welcome. Or what about a silver heart from Tiffanys, designed by Elsa Peretti? (Prices start from pounds 40.) But everyone is different, and I think what means the most is something that comes from the heart.

One Valetine's day the man who later became my husband cooked me a meal (he has a pathological fear of kitchens so this was no mean feat). After he had served up the spaghetti with tomato ketchup that he had lovingly prepared (bless), and poured my favourite wine, he presented me with a Valentine's card, a fabric heart which he had made himself from one of his old shirts and safety-pinned to a bit of card. Inside the heart he had stitched in his Great Frog ring, a silver skull, and a ring that meant a great deal to him. It was special, and it certainly was a classic. As for cufflinks, in fashion, as in life, there should be no rules - only guidelines. You should wear what you want when you want.

Send your fashion problems to: Dear Annie, Independent on Sunday, 1 Canada Square, Canary Wharf, London E14 5DL, or fax them on: 0171 293 2043. Annie regrets that she cannot enter into personal correspondence