A Guide To Choosing Dress Shoes

Whether it’s wedding season, you have an interview coming up or  want to learn about dress shoes, this blog will outline the different types so you can understand how to identify them.

And as always I haven’t been sponsored to write this, just sharing information that I’ve picked up so that it can help you. So strap in!

This is really similar to an Oxford but even less detailed. These were ‘the trainers of the 19th century’ and were a lightweight boot alternative you could run about in.

Look out for laces living free without a stand and no toe cap in sight. Dress shoes like these are perfect for someone with wider feet. With more of a space between the laces, they don’t need to be tied so tight.

In my opinion they are a little basic but no harm in having a pair if that’s the fit that calls out to you. These days you can find many modern takes on these with jazzy fabrics and chunky heels if you’re a thrill seeker with fashion.

A brogue is for someone who enjoys a touch of fun in their shoe. They have an old school dapper to them I think. Brogues can add personality to an outfit really well so even the plainest suits look more interesting.

This design comes from Scotland and Ireland as ‘brog’ is Gaelic for shoe. The signature preforated patterns were origninally punched in to let water out when these shoes were worn in damp conditions.

When the Prince of Wales wore these in the 1930’s golfing, they became more fashionable. Nowadays brogues are a timeless choice that many people pick for occasions like weddings or even just to perk up that work suit.

This shoe style takes its name from the monks who originally wore them as the closed design provided more protection than their traditional sandals.

It’s actually quite similar to an Oxford in shape and construction with the same toe cap sometimes.  The main difference being the fastening is a buckle going across instead of laces.

I enjoy a monk-strap shoe as they are a less picked style that are just as smart as your Oxford or Derby. It’s nice when many people are wearing the same thing to have something slightly different yet still appropriate.

And remember to match the shoe buckle to your other metals like your belt buckle, watch, jewellery etc as you’ll really look like you know what you’re doing.

Loafers became fashion items in 1930’s America and are based on shoes worn by Scandinavian fishermen. You see many woven types even these days harking back to this.

It’s believed that the ‘penny loafer’ term was coined (haha) when young men would put a penny in their loafers for the bus ride home after a night out.

These shoes are usually confused for a moccasin which is more casual. A loafer has more of a proper heel and sole to it whereas moccasins are typically in a suede and have a thin rubber sole.

Lacesless shoes are effortless. Lending themselves to casual dressing just as easily as smart. Many people enjoy them in the summer with a lighter suit fabric. Shorts and a nice shirt work well too. An intentional sock makes them cooler weather ready as well.

I think they are a great classic style that have elegance and a preppyness that works well with lots of outfits.

Yes there’s always chatter about to sock or not to sock. I’d say there’s no right or wrong answer these days. Do what feels like you and suits the occasion. If you like showing that bit of skin but need some support, you can get plenty of hidden socks.

It can be nice to pick a skin tone shade as showing more skin makes you look taller. With a short, a nude shoe will make it look like you have long legs. And it’s good if your suit is a flashy colour and you’d like your shoe to blend in and let the clothing draw that attention.

These badboys started as horse riding boots which even Queen Victoria owned. But it was The Beatles who brought them into the mainstream in the 1960’s. The style is named after Chelsea where they’d hang out. It’s not just the music we have to thank them for!

They tend to sit just above the ankle and have elastic on the sides so you can slip your foot in. Nice and easy again like the loafer. And we like easy 🙂

Boots like a Chelsea are great alternatives to a dress shoe and keep your ankles warm for those colder days. Also good if you prefer having a plain foot with your outfit. Perhaps a printed suit calls for foot simplicity.

If the elastic is in a cool contrasting colour, a roll up could be a nice way to show off that feature and say ‘hey I have style’.

Of course they work perfectly for smart and casual occasions and I think a boot like this will get many wears. Definitely a good piece to have at your disposal.

Even more casual than the Chelsea is the Chukka boot. Charactarised by a round cap-less toe, laces and two or three eyelets. They come up to the ankle typically.

This style is what Clarks are known for and do best in my opinion. After being worn by British soldiers in the deserts in WW2, they became popular civilian wear too. They are commonly known as a ‘desert boot’ to most. You can still find them searching this term online.

If you’re looking for something slightly out of the norm these are another nice alternative to a classic shoe or boot. As a stylist I love suggesting pieces that are less often chosen! Also nice for smartening up a jean as well as making formal look less formal.

All of these styles can be found in the classic suit colours. Your blacks and browns, tans and cherry reds. Which of course are pretty essential to have and I’d say having a couple is a must.

But nowadays there’s such a range of other colours to have fun with too which I do reccomend. Suits and smart dressing have less rules and more room to express yourself. Which is great, have fun with your fashion choices!

Try a pattern, a two tone, a funky lace. Many of these shoe styles have a range of heels these days as well. Chunky platforms and contrasting colours to the upper.

These shoe styles don’t have to be worn with suits. Wear them casually too and play with that mix of dressing up and down your looks.

You also don’t always need to wear a dress shoe with a suit these days. A plain clean trainer has become more accepted. Try good quality sandal in the heat or a boot in the winter. Suits have so much scope and possibilities with creative styling!

Trousers also don’t always have to be long. It can be flattering to have a slightly shorter length. This can make the wearer look taller as sometimes too much fabric can drown us.

Pair your footwear with a fun intentional sock to show off. Perhaps a colour that ties in with your outfit or a funky pattern that expresses your personality in some way. Accessorise and pay attention to detail. Formalwear can be fun 🙂

And that’s a wrap! If you’d like some more personalised advice, please do get in touch and I can help you put together the perfect look for any occasion. Or indeed if you know someone who needs some guidance for a special event, Personal Styling experiences make great gifts.