I'm a 30-year-old man but I still dress like a student

Dear RosemaryI'm turn 30 next birthday and work as a graphic designer in a young agency in the southeast. I tend to dip in and out of various trends but have no real "look". My wardrobe is a mish-mash of stuff I've picked up over the years.

Because I work indoors and don’t do a lot of moving around, my clothes tend to stay in pretty good shape for a long time, so I’ve had some stuff for ages. I feel as if I still dress like a student and I’d love a bit of advice as to what I could do to push me towards a more grown-up but not stuffy look, maybe some advice on what would suit my job but could cross over into home life too. (I have a 20-month-old son and I just got married.)

Some days I wear a hoody and jeans, tomorrow a slim-fit polo and skinny jeans, the day after a shirt and chinos. The only constant seems to be my Converse Chuck Taylors, which I have in black, white and sand.

Steve, by email

Steve, take heart: you’re not the only graphic designer whose job allows them to be perhaps more casual than they’d like.

First, and here is a harsh lesson that all men – and women – would do well to learn: hoodies are not acceptable dress once you have left the confines of college. It doesn’t matter if you’re wearing them in an “ironic” way or if your life and job leave room for you to be supercasual. You are a grown-up, and hoodies are for sports, Sundays and sick days – with no exceptions.

Hoodies aside, your dress options sound quite nice, and there is no reason you should have to hem yourself in with one specific “look”. It can be quite freeing to dress like a shirt’n’slacks man one day and in skinny jeans and a graphic T-shirt the next.

Be sure to always wear the right size. Many men imagine themselves larger than they are (steady on, we’re talking about shirts) and wear items that pucker at the chest and gape at the shoulders, or trousers that gather at the ankles. Avail of the assistance of the sales people looking to liberate you from your money, and get measured.

When it comes to jeans, going for a more tailored style (but not, please, with brown shoes) can make a big difference. Try Scotch Soda (above) at larger Avoca stores – they have a true-blue denim jean that is gorgeous and falls somewhere between casual and dressy. For T-shirts, try Topman and Zara for more fitted and less slovenly shapes.

In general, though, there are three things worth investing in: a stylish coat (I quite like Zara’s, above, faux fur collar aside, €199); a decent haircut, in which a human being takes out a scissors and, in a considered fashion, cuts your hair, rather than razing it all over; and a good shave. Combine these three elements with a pair of skinny jeans and your Converse and, provided there’s not a hoody in sight, you can’t but look dapper.

I need some ankle boots  that are kind to the calves

I’m thinking of my winter wardrobe and want to go down the ankle-boot route. What options are there out there that channel the Isabel Marant/Katie Holmes look, on a skinnier budget, without making my less-than-lithe pins look unnecessarily chunky?

Aoife, by email

Unfortunately, fashion hasn’t quite advanced yet to the stage where designers are inventing ankle boots that flatter the fuller calf. This is because fashion doesn’t care about the fuller figure.

My personal bitterness aside, there is no specific guide to buying (semi-)flattering ankle boots; as calf measurements and curves vary from person to person, it’s a matter of trying on ankle boot after ankle boot to see what works for you.

As a general guide, I would not buy a boot that hits the calf, unless it covers the whole thing. If it cuts your calf halfway up it will serve only to make it look like two unattractive lumps of meat, rather than, er . . . one.

These cowboy ankle boots, from Zara (above, €79.95), take a leaf out of Marant’s book, but at a fraction of the price. They’re leather, too, and they’re not too high so shouldn’t cripple you on the morning journey. The angle of the boot is important, too; they angle down at the front so your legs should appear to emerge from them like a blossoming flower, rather than squashing out over the top.

These tan boots from Buffalo (above, €155) are another Marant-alike on the high street at the moment. From experience, I can tell you that Buffalo’s ankle boots are some of the comfiest out there – it helps that these have a chunky heel and aren’t gravity-defying. They might be a little high on the calf, depending how long your legs are, but they’re worth a try.

These Penneys boots (above, €20) are a little more Acne than Isabel, but at that price, who’s complaining? The colour will look great with denim, especially, and they’re cut low enough on the calf so that they won’t cut it in two. They also come in black.