Where are we with the boots?
I’m so glad you brought up this crucial issue. If you ask me – and you are – proper footwear counts for about 30% of a good day. Wear the wrong shoes, especially this time of year, and your day will be a dumpster fire before you even leave the house. This is why you always need black boots.
Comfort and walking are non-negotiable, but life is too short to wear ugly shoes, so they have to be a little bit fantastic. Ankle boots rather than knee highs, because now you wear wide leg jeans, not skinny jeans (please tell me you wear wide leg jeans, not skinny jeans) and knee highs only work with skirts and dresses.
The key to boots that are cool but also comfortable is to find something chunky with a bit of charm. A plain, flat black boot with a thin sole looks bland. The upgraded boot, with a raised sole and some kind of jazzy buckle, has attitude. My favorite boots were bought last season from Jigsaw, but they’re basically identical to the Maldow boots (£200) and have a gold zip that elevates them from a dog-walker to something Camille from Emily in Paris could wear to a boulangerie.
Mountaineering style laces are another detail that can really elevate the boot. I love the Barbour Fairfield boots, with silver D-ring eyelets for laces and a soft padded top for added comfort. I’ve seen them discounted at a few sales this month. If you like the look of a lace-up boot but can’t be bothered with the actual lacing, I’d highly recommend the chunky lace-up boot from M&S, which has a hidden zip on the inside of the ankle. I swear by M&S for the most affordable decently made shoes on the high street and these have a sleek silhouette that looks way more expensive than the £45 price tag.
Jess Cartner-Morley
If I don’t have a uniform, is it okay to wear the same thing to work two days in a row?
Obviously this is a trick question. You can wear whatever you want. But there are ways to change up your wardrobe so no one realizes you’ve been wearing the same thing four days in a row. I do it all the time.
I think I dress like I’m making soup – start with soup and then add different flavors each day. Wear a few basic pieces, ideally in dark fabrics, that act as your “suit” – then rotate tops, shoes and accessories. For example, I have two dark, slightly oversized jackets/blazers (one from Acne Studios via Vestiaire and one from Reformation). I prefer jackets that hang below the butt because you can wear them with any cut of pants. I add dark crepe, viscose or tencel trousers to them as they won’t lose their shape – I like Ganni’s viscose trousers as they are easy to clean. I prefer my “suit” to be dark blue or black, but the shades don’t have to match.
Then comes the changing parts: a bright V-neck T-shirt or a printed blouse, and sometimes a belt, because it changes where the same pants fit and whether you’re going to turn them up or not. As for shoes, everything is available. One day I will wear this “suit” with black Asics. Second, I’ll tuck my pants into my socks and wear them with heeled boots.
Avoid wearing light-colored shirts repeatedly (dirt collects in the collar) and avoid silk and linen (they wrinkle in an hour, let alone two days). Simple things like switching earrings from hoops to studs are great distractions. Same clothes, different styling.
Morwenna Ferrier
What can I wear in winter if I don’t like tights?
The ladder, the itchiness, the constant need for adjustment – there’s a lot to hate about leggings. Fortunately, the sock industry is starting to pay attention, so they’re worth trying again.
First, sizing. Most tights use a generic S, M, L, etc. If you’re between sizes or at the top end of the range, always go bigger. Tights are usually smaller (cheaper) and there’s nothing more uncomfortable than a drawstring waistband. If you’d rather skip the belt altogether, buckles are a good option.
There is some welcome news about ladders: Hēdoïne has a ladder-free guarantee; Legwear Co has tested its products for 100 washes with a 60-day guarantee; and Canadian brand Sheertex (from £38 and XS to 3XL) comes with a three-month guarantee against tearing, laddering or snagging, thanks to the fabric used in the bulletproof vests. I realize you probably won’t get them back if they do a ladder – who has time? – but some of these brands really work.
If tights are still an absolute no, just try a longer hem. Pair the midi skirt with knee high or chunky boots and wear with a pair of Uniqlo thermal socks or add a fleece insole for added comfort.
Chloe McDonnell
What should I wear for my commute?
Moving to Kent added an extra train journey to my day, so I’m confident when I say that layers are your friend. Things you can easily slip on, slip into your travel bag and wear again relatively wrinkle-free at the other end. You don’t have to bring a cover to the office.
Start with a pair of tailored wide leg trousers (my current favorite are from The Frankie Shop). Comfortable to sit in during a delay, they look good with a long sleeved body (Everlane’s are sustainable and long on the body) to form a smart/casual “base”.
An oversized shirt can be layered on top followed by an unstructured blazer or a soft chunky knit with a relaxed bomber jacket. A trench coat is the ideal top layer as it is light enough to fit on the luggage rack. I also carry a large shoulder bag – it stands upright on the floor of the carriage.
The big problem is footwear, of course. To avoid changing shoes, try GH Bass for smart but comfortable loafers and Cos for more than a loafer/pump hybrid: Springcourt has a great selection of minimalist sneakers that are also super comfortable – I’m a fan of the heavy canvas.
A word to the wise: no matter how chic your jumpsuit is, it’s probably best to avoid it for your daily commute in case you have to use the train toilet.
Melanie Wilkinson
I hate jeans – can you change my mind?
Jeans are the cornerstone of every modern wardrobe. Find the right ones and you’ll never want to wear anything else. One caveat – you will have to try a lot. It makes sense to order a few pairs online (check the return policy) and try them on at home with your own clothes. For your first search, go wide with different shapes, colors, sizes and lengths and try them on with tops you wear often. This will give you an idea of what the person wearing the jeans actually looks like.
Next, consider the shoes to get the right length. The jeans should lie over the sneakers and cover your socks, but the boots should touch just below the ankle. If you are a fan of socks, experiment with a short length. This applies to sneakers and sandals in the summer.
Skinny jeans will always have their place, but baggy, wide-leg jeans are the thing right now. Try Weekday or Acne. A darker shade is always classic, especially with straight cuts. APCs are the expensive OG here, and Uniqlo do 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 color for a long time.
Craft denim is now a category of its own. For those with the cash, Japanese brand Kapital produces jeans that look like works of art made at Woodstock. Of course, you can be creative and make your own version.
Lauren Cochrane
Are there any non-athletic trainers acceptable for a middle-aged man?
Yes, although it’s best to leave simple styles to the kids. Stay classic with modest styles from Nike and New Balance. The latter’s collaborations with brands like Junya Watanabe and Aimé Leon Dore offer an insider level to the style label while remaining totally wearable every day.
Experiment with color, but to get the most out of your sneakers, avoid bright shades. That’s not to say you shouldn’t wear pink—popping out in sneakers is very comfortable, especially if you’re wearing a lot of neutral tones. Just keep it relatively subtle. Middle-aged poster-boy Brad Pitt wore Gucci’s boldly colored collaboration with Adidas on the red carpet last year and topped the best-dressed list. Style trick: the standard Adidas Spezials come in a variety of shades for less (£80) and are undeniably cooler.
One piece of advice from Belgian label Dries Van Noten is that the Francis Bacon color palette will always serve you well. By this I mean the pairing of two (or three) colors that are slightly different – one can be pale, the other lighter, say khaki and pink, or rust and pale blue. The Air Max Pre-Days come in some of the best color combinations, and if you size up, it’s worth checking out the women’s styles as well.
If that sounds too much like hard work, stick to neutrals. New Balance’s M990GB2 in Grey/Cream look just the right amount of fashion, and its 997H style in rust suede with white detailing (£95) is a good toned down edition. To design your own, Nike offers a customization service Air Max 90 – £152.95 for UK sizes 5½ to 14.
Helen Seamons
My daughter wants a purse. He is 17 years old. Help
As a bag lover, I clearly remember my first bag and how grown up it made me feel. They are also practical, reducing the likelihood of your headphones, phone or wallet being left on the bus.
While a designer bag might be out of reach for your 17-year-old self, there are plenty of high-street dupes out there, but without the price tag. Monki has great choices: its Y2K-style padded baguette bag from £20 is a real trend-setter.
Another plus of the high-street bag is that it can take on several different styles: a small shoulder bag for going out on the town with friends, plus a shopper style with a laptop compartment for work/college/university.
Pull and Bear has a great alternative to the viral nylon Prada bag for £17.99. If she needs something roomier, the newly revived Topshop (available at Asos) has a great designer-looking bag with woven details that looks more expensive than its £25 price tag and is great for carrying books and a water bottle.
If you’re looking for a slightly higher price, JW PEI is an LA brand with styles in colors to suit all personalities: its Eva bag, £59, is smart enough for going out and cool enough for everyday.
Depop is the place to go for something a little more unique – there are so many favorites and vintage bags, like this 1990s Roxy shoulder bag for £30. I can guarantee her friends won’t have the same.
Rosalind Donoghue
For more tips, articles and the answer to the weekly style problem, sign up to the Guardian’s new Fashion Statement newsletter