Purveryors of smart casual brands know this well: Their designs are made with a smart mix-and-match mode in mind.
New-to-town Japanese casualwear retailer Uniqlo, for example, has created basic skinny jeans in eight colours and tank tops in 15 trendy colours including indigo and blush pink this season.
'A simple T-shirt can be worn in many ways,' says Uniqlo Singapore's marketing division manager Yasuhiro Hayashi.
'We believe that each customer has his or her own distinct style and will come up with a way to wear it and look smart.'
American casualwear giant Gap, meanwhile, has taken the more classic route, focusing on 'classic casuals' like chinos and cardigans that can go easily with more on-trend duds like a jumpsuit or sequined top.
Says its regional marketing communications manager Jimmy Lim: 'Someone may wear a pair of skinny jeans with high heels while another pairs them with sneakers.
'They are two completely different looks that show off two different personalities and that's all part of style.'
We get four stylemeisters - home-grown stylist Jerome Awasthi, local actress Pamelyn Chee, American model Rory Greer and housewife-cum-socialite Cheryl Lee - to share how they put the chic into casual.
TAKE IT EASY
Here are some tips for turning casual dressing into a class act.
Pile it on: Layering tops of different lengths such as a cropped vest over a long tank top adds contrast and texture, making you appear dressier than you actually are.
Pairing formal separates such as a cotton blazer with more casual counterparts creates the same effect.
Bling it on: Jewellery - be it a basic gold bangle or statement necklace - lends a touch of formality and can turn an outfit from dull to dazzling in a jiffy.
Boho boo boo: Unless they are meant to be, baggy clothes risk making you look like a bag lady.
Your tee should just skim your figure and straight-cut jeans - one of the most classic denim cuts - should sag only slightly at the knees when worn.
Get shorty: Shorts - be they bermudas, cropped jeans or hot pants - will always look informal. The trick is to watch the length.
Too short - anything above mid-thigh - and you might come across as tarty. Too long - anything below the knee - is likely to make you look like a style dork.
Material girl: Fabrics like linen and light knits always look more luxe than regular cotton.
Flip-flops flop: Tall, stylish people may be able to carry these off, but we suggest you banish flip-flops from your wardrobe unless you are wearing them to the beach.
Choose multi-strapped or embellished sandals, sneakers or ballet flats, which look less sloppy but are just as comfy.
If you insist on wearing slippers, pair them with a dressier outfit such as a maxi dress or a tank top and cotton pants for a look that is easy yet eclectic.
FLATS ARE FAB
Home-grown actress Pamelyn Chee lived in fashion capital New York for seven years but finds the laidback vibe of Los Angeles more inspiring.
A self-described casual dresser, the 25-year-old is now back in sunny Singapore.
The star of the recent Channel 5 telemovie, A Kucinta Family Reunion, who used to fly to the City of Angels regularly for acting work, notes: 'The weather there is a closer match to Singapore's, yet the way the people there dress isn't sloppy.
'Instead of T-shirts and slippers, the girls wear sundresses or pair a well-cut tee with jeans. It's a sunny place, but they still put in effort.'
Indeed, she exuded effortless chic when she turned up for this photo shoot wearing skinny jeans, a printed tank top and '$2.50 Tat Sing slippers'.
Yep, the star of the upcoming local film Basket Ballet is right at home in flip-flops - she has 15 pairs.
The 1.71m head-turner says: 'I don't usually like wearing heels because I'm already quite tall.'
She has this tip, though: 'I avoid looking sloppy by sprucing up with accessories and layering. You can do casual dressing well just by injecting some personal style.'
Casual dressing is... when style meets comfort at a decent price.
My personal casual style is... a well-cut top and jeans or a sundress that's not too short, with flip-flops or ballet flats. I also accessorise with belts, jewellery and a hairband.
My favourite casualwear retailers are... home-grown streetwear brand Collage in Far East Plaza, multi-label store Black Market in Jalan Pisang, which stocks unique pieces, and multi-label boutique Blackjack in Forum for designer streetwear.
I once dressed too casually... for a film gala last year. My manager told me about it at the last minute so I headed down in my work clothes of T-shirt and jeans. To my horror, everyone else was really dressed up. But the damage was done so I sat through the whole film anyway.
The key to stylish casual dressing is... to accessorise, be it with a wide belt or tiny pendant. Make sure your hairstyle matches and maintain good skin. It's about the whole package.