fashion . Styling Tips

5 Classic Shoe Styles Every Woman Should Own

Walk a mile in these timeless designs

If good shoes take you to good places, then great shoes that are designed in timeless silhouettes are bound to bring you to even better destinations. While it’s fun to splurge on the occasional trendy sneaker or mule to upgrade your style game, it’s also wise for you to invest in classic shoe styles that will fit right in with the items in your wardrobe. Ahead, we round up five must-have classic shoe styles every woman ought to have in her ‘shoedrobe’.


Slip-on sandals


castaner net a porter espadrilles charles keith slide on sandals

(Left) Castaner ‘Palma’ canvas espadrille slides,~SGD118/USD85.49 (Photo from: net-a-porter.com). (Right) Charles & Keith Buckle Double Strap Slide Sandals, SGD46.90/~USD34 (Photo from: charleskeith.com)


The ‘stylish cousin’ to the flip-flop, slip-on sandals are as comfortable and easy to wear yet look slightly dressier. Rock up to a cafe in them without looking underdressed. For a luxe yet ethically conscious footwear option, consider Castaner’s ‘Palma’ slides, which are locally made in Spain using natural linen and cotton. If you prefer designs that bear modern touches, check out Charles & Keith’s double strap sandals which feature sleek gold-tone detailing.


How to style them: Slip-on sandals look best when paired with casual-cool ensembles, so wear them with natural-looking separates, such as a beige linen skirt or a pair of loose cotton trousers.


White sneakers


reebok sneakers asos exclusive converse chuck taylor sneakers

(Left) Reebok Club C double trainers, SGD138.99/~USD101 (Photo from: asos.com). (Right) Converse Chuck Taylor sneakers, SGD83/~USD60.34 (Photo from: sg.urbanoutfitters.com


A must-have casualwear staple that deserves a permanent spot in everyone’s wardrobe. White sneakers are a fashionable, streetstyle-approved alternative to other classic forms of covered footwear, such as ballet flats and loafers. Hoping to rock a little colour on your feet? Opt for Reebok’s Club C double trainers, designed with cool lilac and iridescent details. For a pair that ‘ages’ beautifully over time, look to Converse’s Chuck Taylor All Star high top sneakers, which are made of lightweight and durable canvas.


How to style them: Keep them clean and pristine and you’ll have the perfect finishing touch to an otherwise dark muted ensemble. Alternatively, break them in and wear them with your favourite casual separates, such as denim jeans and A-line mini skirts.

Ankle boots


dear frances maroon boots by far brown suede boots

(Left) Dear Frances ‘Spirit’ boot, SGD825/~USD599 (Photo from: dearfrances.com). (Right) By Far ‘Lara’ suede ankle boots, SGD185/USD134.27 (Photo from: net-a-porter.com)


These are silhouette-slimming shoes which help upgrade your style game while giving you a little height boost. Ankle boots are great especially when you’re in the mood to play dress up, be it for a movie date with your beau or for a day of shopping with your girlfriends.


Go minimal with Dear Frances’s ‘Spirit’ boots, which have become a cult favourite among fashion influencers. These shoes feature a leg-lengthening effect and are designed with a solid, block heel to provide added support for your heel area. For a more vintage-looking design, add By Far’s ‘Lara’ suede ankle boots to cart. Made from lovely brown suede, these boots are a welcome addition for those who favour brown and beige-coloured clothing.


How to style them: Avoid tucking your trousers into your boots as they’ll make your legs appear shorter. Pair them with a cropped pair instead, or flaunt your pins with your go-to high-waisted shorts.


High-heeled pumps


charles keith nude asymmetrical pumps asos design black pumps

(Left) Charles & Keith asymmetrical pumps, SGD53.90/~USD39.18 (Photo from: charleskeith.com). (Right) ASOS Design pointed high heeled court shoes, SGD24.36/~USD17.71 (Photo from: asos.com)


Power pumps will have you walking with a spring in your step. Pumps may have a bad rep for being uncomfortable at times, however, they are still an important style essential that will help you dress the part amongst more formal settings and occasions. Go nude with Charles & Keith’s asymmetrical pumps, which help you create the illusion of longer-looking legs. Alternatively, slide into ASOS Design’s jet black court shoes, which are made of low-maintenance, faux suede material. 


How to style them: As they go with virtually everything in your wardrobe, go forth and experiment with different looks whenever you don this classic pair of heels. Wear them with a pencil skirt and button-down shirt for quick trips to the office, or with a maxi dress if you wish to appear taller and leaner.

Strappy heels


who what wear asos orange beige sandals shein white sandals

(Left) Who What Wear ‘Perla’ mid-heeled sandals, SGD74.11/~USD53.81 (Photo from: asos.com). (Right) Shein stiletto heeled sandals, SGD36/~USD26.17 (Photo from: sg.shein.com


A flattering, pedicure-flaunting shoe design that looks good on almost every woman, strappy heels are worth investing in as they provide the comfort that comes from wearing flip-flops while giving you a much-needed height boost. We love Who What Wear’s ‘Perla’ mid-heeled sandals as they are a modern, stylish take on the '90s slingback heel. For a bolder and trendier version of this classic design, Shein’s stiletto-heeled sandals are a great option to consider a well.


How to style them: Strappy sandals look best with a dress or skirt with slit details as they will also help you to visually lengthen your frame. However, if trousers are more of your cup of tea, do cuff the hems of your trousers and flaunt your ankles in order to achieve a similar leg-lengthening effect.


Which of these classic shoe styles do you like best?


(Cover photos from: charleskeith.com, shein.com and asos.com)



Next, learn how you can ace Korean fashion with just a few wardrobe staples.