Women’s Shoes: How and What to Wear

You can never have too many shoes”. and while some might disagree, we certainly think that the more shoes the better.

But all these shoes come with a problem: sometimes it’s just too tricky to decide what to wear! Well, there are several things you need to consider, such as the colours in your outfit, the proportions of your clothing and even the size of your feet. By thinking about these things, and following our style tips below, you’ll soon find that you can match your shoes to occasions and outfits with ease!

What Women’s Shoes to Wear With Jeans

A large proportion of us live in jeans outside of work, whether skinny, boyfriend, or bootcut. But finding the right pair of shoes to go with these can be tricky. Are ballerinas best? What about heels? Here are our tips for finding the right women’s shoes to wear with jeans.

What Ladies’ Shoes to Wear with Skinny Jeans

Our love affair with skinny jeans shows no sign of going away. They’re an absolute wardrobe staple so we thought they deserved their own section here.

The good news is that there’s a shoe for every season and occasion that you can pair with your skinny jeans. On the other hand, the slim silhouette can create proportion issues especially if you’ve got larger feet, so you need to tread carefully, go for more streamlined styles and avoid anything too heavy or chunky.

For Everyday:

For colder days, flat ballet pumps or women’s loafers are ideal. The lack of heel means they’re comfy for when you’re on your feet all day, whether you’re running errands, going shopping or at work (if you work in a more casual environment).

Round toe or pointed toe, it’s up to you. But if you’ve got larger feet, be aware that a pointed toe will elongate your feet and possibly affect the proportions versus your jeans.

For a casual look, ballerina pumps or moccasins can be teamed with skinny jeans and a striped Breton top. Make sure the colour of your ballet pumps works with the colour of your jeans (a very dark ballet pump could look a bit heavy next to very pale jeans).

Women’s brogues are another alternative for casual looks. Classic, neutral colours look lovely, but so do unexpected twists such as metallics and contrasting colours.

For a smarter look, again why not try a pair of loafers? Dark or mid-coloured skinny jeans should be worn here (leave paler ones for more casual looks). Match them with smart leather loafers in darker colours such as black or burgundy, or neutrals such as tan and nude, and a printed blouse or a long cardigan over a pretty top.

If wearing to work, by all means wear (closed-toe) heels, but avoid anything too high, platformed or strappy (these should be saved for cocktail hour – more on this later). Black heels and black skinny jeans look wonderfully streamlined and pair well with tailored blazers for the office. If your shoes have ankle straps, turn up the hems to show these off.

In the summer, sandals look great with skinny jeans. In this case, due to the straps, ankle-grazing jeans are better (or turn up your favourites if they’re slightly longer), as this will show off the whole shoe. Delicate, detailed flip-flops or thong sandals are a pretty choice for casual wear but should be avoided for work. These go well with floaty tops and paler-coloured skinny jeans.

Flat Greek or gladiator style sandals are a good alternative if you’re not particularly into floaty summer styles. These look great when paired with darker coloured jeans and a T-shirt.

For Nights Out:

Skinny jeans are the perfect piece of clothing to take you from day to evening. Again, darker colours are best. Black is best if you’re going somewhere a bit smarter, as quite often they’ll look less like jeans (some places don’t allow jeans so always best to check), but mid to dark blue also works well.

Now’s the time to put on your heels. Strappy or pumps, either works. Here you can go to town on bright colours and embellishments, so the main thing is to show them off. That means no jeans that cover the tops of your shoes. Wear ankle grazers or turn them up. Add a sparkly top under a tailored blazer and you’ve got a classic evening look that’ll take you from restaurant to bar to club.

If bright colours or bling aren’t your thing, you can’t go wrong with a pair of black strappy heeled sandals to add a bit of a dressy edge to your outfit. Nude strappy sandals will also go with most outfits so are a perfect staple pair of shoes to have in your wardrobe.

If you’re not a fan of heels, or you want to dance the night away, why not try some embellished flat ballet pumps or sandals? They’re perfect for dressing up an outfit. Pair with your skinnies, a pretty top and some sparkly accessories and you’re good to go!

Shoes and Heels to Wear with Other Types of Jeans

We’ve talked about wearing heels with skinny jeans above, but what about other types of jeans? Boyfriend jeans are enjoying a bit of a moment right now, but bootcut jeans are always waiting in the wings, so what shoes to wear? Here we go…

Boyfriend Jeans:

Boyfriend jeans are so-called because they look like they could have been borrowed (or stolen!) from your boyfriend. They’re comfy and very relaxed in terms of fit which gives them a very casual look, so unless your workplace has a relaxed dress code they should not be worn for work.

Wearing heels with boyfriend jeans may seem weird when you think about the style, but it’s actually this unexpected-ness that makes this combination work. The casual jeans look amazing when paired with smart, heeled shoes, and make a great combination for a (more casual) night out. In this case, keep your top plain (maybe add some statement earrings) and let your shoes do the talking.

For everyday, casual looks, boyfriend jeans (as you might expect) look great when paired with trainers. Whether these are the slip-on kind that are fairly popular at the moment, or the classic sneaker kind (think Converse or Reebok-style), they all look super-stylish for minimal effort, the epitome of “I just threw this on”. For a bit of a twist, try metallic or embellished women’s trainers to add a bit of sparkle to a casual look.

Bootcut Jeans:

Bootcut jeans have been making a bit of a stealthy comeback, so we can’t forget them! While the obvious answer is that you wear boots with bootcut jeans, this doesn’t always have to be the case. The shape of bootcut jeans means that they lend themselves well to heeled shoes, so pretty much anything goes (avoid wedges though).

For daytime, opt for a chunkier heel, either as a sandal or a pump. Ideally you want to go for a heel that’s between 1 and 3 inches. Add a pretty blouse and a light jacket and you’ve got a smart-casual daytime look that’s perfect for meeting up with friends, or running errands.

For evenings, break out the strappy sandals and stilettos! The daintier styles look amazing with bootcut jeans. Black is a staple for a reason, but bright colours and metallics will provide a focal point for your outfit. Add a pretty top and you’re ready to go!

What Women’s Shoes Should I Wear with Trousers?

So now you’re sorted with what shoes to wear with your jeans, what about other types of trousers?

Cropped trousers:

With cropped trousers, it’s best to avoid heavy or chunky shoes as they’ll break up the look of your outfit. Keep shoes fairly dainty and streamlined for the most elegant looks.

Mid-heeled, peep-toe pumps look lovely with cropped trousers as the heel lengthens the leg. The same applies to wedges. However if opting for wedges, make sure they’re strappy or cut lower on the foot to offset the chunkiness of the heel.

For flat shoes, ballet pumps can work well, but it depends on the style of trouser you’re wearing. If you’re wearing slim-fit or cigarette-style trousers, these are a classic accompaniment and very Audrey Hepburn, but if your trousers are wider then ballet pumps will look too dainty.

Palazzo or wide-leg trousers and jumpsuits:

After years of skinny-fitting trousers, wide-legs are back with a vengeance. They’re great because they’re comfy and relaxed, but paired with the wrong shoes they can look very unflattering.

Avoid trainers, loafers, moccasins and other more substantial styles as these will create too much of a bulky look. Instead, you should opt for pretty ladies’ sandals (espadrilles are a stylish choice for day to day or on holiday), delicate flat shoes or heeled pumps. These styles will each create a contrast with the wide trousers that is super-stylish in its own way.

Keep tops fitted to avoid a too-relaxed look, and you’re good to go!

What Shoes to Wear with Skirts and Dresses

Now we’ve covered jeans and trousers, what about skirts and dresses? Again, there’s a shoe for every outfit, it’s just a question of finding the right pairing…

What Shoes to Wear with Pencil Skirts

Pencil skirts are a wardrobe staple for many women due to the fact that they’re figure-slimming and work for pretty much any occasion.

For work, you can’t go wrong with a classic court shoe. Stick to more neutral colours if you want something that goes with everything and you’ll have the foundation for the perfect office outfit.

For nights out, you can funk up your pencil skirt a bit. Even a plain black one can be taken from day to night with the right shoes! The key is heels. Try a pair of brightly-coloured or patterned courts or funky strappy sandals, but make sure these are the focal point of your outfit – avoid clashing colours!

What Shoes to Wear with Maxi Skirts and Dresses

The great thing about maxi skirts and dresses is that they look as fabulous with flat shoes as they do with heels, so you can be comfy as well as stylish! However, sandals work best with this type of look as they’re less heavy, so it’s a good look to have in mind for summer months!

Flip flops, gladiator sandals or plain, flat sandals all look lovely with maxi dresses. If you’ve got a very highly-patterned dress, go for a more neutral shoe (black, tan and nude all work well). Metallics, particularly gold, work well for summer months as well.

For a more co-ordinated, formal look, why not try picking a single colour out of your dress and matching your shoes to that?

If you’re heading out on the town, wedge sandals make for a pretty, relaxed and summery look that’s still dressy enough to party in. Keep them strappy to offset the chunkiness of the heel.

What Shoes to Wear with Mini Skirts and Dresses

With mini skirts and dresses you have to be careful and err on the right side of scandalous. That means avoiding very high and very strappy stilettos and instead opting for lower, more chunky heels or flat shoes.

You should also avoid more bulky styles such as Oxfords as they’re just too chunky to pair well with shorter skirts. The one exception to this is trainers, more of which below.

Low to mid height block heels are all over the shops right now so there’s a plethora of choice. These look lovely with mini skirts. Wear with tights when it’s a bit colder and go bare-legged for summer.

For a more casual look, flat sandals bring a relaxed, summery vibe on warmer days, and work in pretty much any style or colour. Avoid flip flops, however, unless you want to look like you stepped out of The OC.

Also on the more casual side, and perhaps surprisingly, trainers work well with mini skirts and dresses. Keep to classic, less bulky styles and you’ll have a great day-to-day look that’s also super-comfy and works throughout the year!

Conclusion

When selecting the right pair of women’s shoes to wear, it needn’t be tricky. As we’ve discovered, there really is a shoe for every occasion, and every outfit, and by following our top tips, you’ll be the best dressed (and shod) wherever you go!