Can you wear the same thing to work two days in a row? Our experts answer your fashion dilemmas

Where are we at with boots?

I am so pleased you have raised this crucial issue. If you ask me – and you have – getting footwear right counts for about 30% of having a good day. Wear the wrong shoes, especially at this time of year, and your day is a bin fire before you’ve walked out of the door. This is why you always need a pair of black boots.

Comfort and walkability are non-negotiable, but life is too short to wear ugly shoes, so they need to be a bit fabulous. Ankle boots rather than knee-highs, because you are now wearing loose-leg jeans rather than skinny (please tell me you are wearing loose leg jeans rather than skinny) and knee-highs only work with skirts and dresses.

The key to boots that are cool as well as comfy is to find something chunky and with a bit of flair. A plain, flat black boot with a thin sole looks blah. A beefed-up boot, with a ridged track sole and some kind of jazzy fastening, has attitude. My most beloved boots are a previous-season purchase from Jigsaw, but basically identical to the Maldow boot (£200), and have a gold front-zip fastening that elevates them from dog-walking boots to the sort of thing Camille from Emily in Paris might wear to the boulangerie.

Hiking-style lace ups are another detail that can really lift a boot. I love the Barbour Fairfield boots, with silver D-ring eyelets for the laces and a soft padded top edge for extra comfort. I’ve seen them discounted in a few of this month’s sales. If you like the look of a laced-up boot but can’t be bothered with the actual lacing, I’d strongly recommend the chunky lace-up boot from M&S, which has a concealed zip fastening at the inner ankle. I swear by M&S for the most affordable decently made shoes on the high street, and these have an elegant silhouette that looks much more expensive than the £45 price tag.
Jess Cartner-Morley

If I don’t have a uniform, is it OK to wear the same thing to work two days in a row?

Obviously this is a trick question. You can wear what you want. But there are ways of recasting your wardrobe so no one realises you’ve worn the same thing four days in a row. I do it all the time.

I think of getting dressed like making soup – start with the broth, then just add different flavours each day. You wear a few base pieces, ideally in dark fabrics, which act as your “suit” – then rotate tops, shoes and accessories. For example, I have two dark, slightly oversized jacket/blazers (one from Acne Studios via Vestiaire, and one from Reformation). I prefer jackets that hang below the bum because you can wear them with any trouser shape. To these I add dark trousers made from crepe, viscose or Tencel as these won’t lose their shape – I like Ganni’s viscose trousers because they’re also easy to clean. I prefer my “suit” to be navy or black, but the shades don’t need to match.

Then come the changeable parts: a bright V-neck T-shirt or a print blouse, and sometimes a belt, as this changes where the same trousers sit, and whether you tuck or not. Shoes-wise, it’s all up for grabs. One day I’ll wear this “suit” with black Asics. Another, I’ll tuck the trousers into socks and wear with heeled boots.

Avoid repeat-wearing light-coloured shirts (dirt builds up in the collar) and avoid silk and linen (they crease in an hour, let alone two days). Simple things like switching your earrings from hoops to studs is a great distractor. Same clothes, different styling.
Morwenna Ferrier

What can I wear in winter if I don’t like tights?

The laddering, the itchiness, the constant need to adjust – there’s a lot to hate about tights. Thankfully the hosiery industry has started paying attention, so it’s worth trying them again.

First, sizing. Most tights use generic S, M, L etc. If you’re between sizes or at the upper end of a range, always go bigger. Tights are typically made smaller (it’s cheaper) and there’s nothing more uncomfortable than a waistband that digs in. If you’d rather skip a waistband altogether, hold-ups are a good option.

On laddering there is welcome news: Hēdoïne has a ladder-free guarantee; the Legwear Co has tested its products to last 100 washes with a 60-day warranty; and Canadian brand Sheertex (from £38 and XS to 3XL) comes with a three-month guarantee against ripping, laddering or snagging, thanks to fabric used in bulletproof vests. I realise you probably won’t take them back if they do ladder – who has the time? – but some of these brands really do work.

If tights remain an absolute no, just try a longer hemline. Team a mid-length skirt with knee-high or chunky boots, and wear with a pair of Uniqlo thermal socks or add a fleece insole for extra cosiness.
Chloe Mac Donnell

What should I wear for my commute?

Moving to Kent has added an extra train journey to my day, so I am confident when I say that layers are your friend. Things you can slide off easily, shove in a bag for the journey, and put on again still relatively crease-free at the other end. You don’t need to bring a change of clothes for the office.

Start with a pair of wide-leg tailored trousers (my favourites at the moment are from The Frankie Shop). Comfy for sitting through delays, they look good with a long-sleeve bodysuit (Everlane’s are sustainable and long in the body) to form a smart/casual “base”.

An oversized shirt can be layered on top followed with an unstructured blazer, or a soft chunky knit with a slouchy bomber jacket. A trenchcoat is the ideal top layer as it’s light enough to be stowed on a luggage rack. I also carry a large-ish tote bag with shoulder straps – it will sit upright on the carriage floor.

The big issue is footwear, of course. To avoid switching footwear, try GH Bass for smart but comfy loafers and Cos for more of a loafer/pump hybrid: Springcourt has a great selection of minimal trainers which are also super comfortable – I’m a fan of the heavy canvas.

A word to the wise: however chic your jumpsuit is, it’s probably best avoided for the daily commute in case you need to use the train loos.
Melanie Wilkinson

I hate jeans – can you change my mind?

Jeans are the cornerstone of any modern wardrobe. Find the right ones and you’ll never want to wear anything else. One caveat – you’ll need try loads on. There’s merit in ordering a few pairs online (check the returns policy) and trying them on at home with your own clothes. Go broad for your first search, with different shapes, washes, sizes and lengths, and try them with tops that you often wear. That way you’ll get an idea of what the jeans-wearing you actually looks like.

Next, think about shoes, to get the length right. Jeans should sit over a pair of trainers and cover your socks, but hit just below the ankle with boots. If you’re a statement sock fan, experiment with a cropped length. That works for trainers and sandals in the summer.

Slim-leg jeans will always have their place but at the moment, baggy wide-leg jeans are the thing. Try Weekday or Acne. A darker wash is always classic, especially with straight-leg styles. APC are the pricey OGs here, and Uniqlo does a more affordable version: their Selvedge Regular Fit Jeans – at a very reasonable £39.90 – often sell out because they fit well and keep their colour for ages.

Craft denim is now a category in and of itself. For those with money to burn, Japanese brand Kapital makes jeans that look like works of art made at Woodstock. Of course, you could get creative and make your own version.
Lauren Cochrane

Are there any non-sport trainers acceptable for a middle-aged man?

Yes, though it’s best to leave the bells-and-whistles styles to the kids. Keep it classic with pared-back styles from Nike and New Balance. The latter’s collaborations with brands like Junya Watanabe and Aimé Leon Dore offer an insider level of style cachet while remaining completely wearable every-day.

Experiment with colour, but to get the most wear out of your trainers, avoid bright shades. This doesn’t mean you shouldn’t wear pink – a pop on a trainer is very pleasing, especially if you wear a lot of neutrals. Just keep it relatively subtle. Middle-aged-male-style-poster-guy Brad Pitt wore Gucci’s bold coloured collaboration with Adidas on the red carpet last year and topped the best dressed lists. Style hack: bog standard Adidas Spezials come in a variety of shades at a lower price tag (£80) and are arguably cooler.

One tip, from Belgian label Dries Van Noten, is that a Francis Bacon colour palette will always serve you well. By this I mean pairing two (or three) colours that are slightly off kilter – one can be sludgy, the other brighter , say khaki and pink, or rust and pale blue. Air Max Pre-Days come in some of the best colour combos, and if you take a smaller size it’s worth looking at the women’s styles too.

If that sounds too much like hard work, stick with neutrals. New Balance’s M990GB2 in grey/cream look the right amount of fashion and its 997H style in rust-coloured suede with white accents (£95) is a good dialled-down colour edition. To design your own, Nike offers a customise service on Air Max 90 – £152.95 for UK sizes 5½ to 14.
Helen Seamons

My daughter wants a handbag. She’s 17. Help

As a bag person, I distinctly remember my first handbag and how grown-up it made me feel. They are practical too, minimising the likelihood of earpods, phone, or wallet being left on the bus.

While a designer bag might be out of reach for your 17-year-old, there are plenty of high-street dupes but without a price tag. Monki has some great choices: its £20 Y2K-style padded baguette bag is bang on trend.

Another plus of a high-street bag is she could get a couple of different styles: a small crossbody bag for going to town with friends, plus a shopper style with room for a laptop for work/college/uni.

Pull and Bear has a great alternative to the viral nylon Prada bag for £17.99. If she needs something roomier, newly revived Topshop (available at Asos) has a great designer-look tote with weave detail that looks more expensive than its £25 price tag and is great for carrying books and a water bottle.

If you’re going for a slightly higher price point, JW PEI is an LA brand with styles in colours to suit all personalities: its Eva bag, £59, is smart enough for going out and cool enough for every day.

Depop is the place to look for something more unique – it has so many preloved and vintage bags, like this 1990sshoulder bag by Roxy at £30. I can guarantee her friends won’t have the same.
Rosalind Donoghue

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