The more casual of the tailored garments, the sports jacket is an easy starting point to adding a little more sophistication to your outfit. With a wide range of patterns on offer, opt for softer, more relaxed lines and mix it up with chinos or jeans and a pair of sneakers, so that you don’t find yourself in the sartorial deep end. Other easy options include shirt jackets in summer and bombers for winter. And if you’re feeling really ambitious, an overcoat works well with this style—the key is working more layers in thinner fabrics to keep the bulk down.

Image: Nam Nguyen

In an effort to make the suit more relaxed, and not just a workplace uniform, they’re frequently are being mixed with polos, t-shirts, sneakers, gilets and other streetwear items. And I’m not talking about tall tees here, although I’m sure it’s been done. The suit, especially if it’s well made, can be beaten as it moulds to your body. Pair it with a polo and some plimsolls (AKA slip-ons) for a more grown-up take on a group coffee catch-up.

Image: Nam Nguyen

Jeans have been done, so what’s next? The Canadian tuxedo? Can we do double denim and not look like we want to chop down a tree? The beauty about tailoring is any fabric can be used to create a suit and we’re seeing a few more denim blazers popping up in the market lately. Some are even taking it to another level and rocking the three-piece denim outfit. Yes, we see more hints of workwear in this than the purities of street but, you have to admit, it’s easier to pair with a shirt and tie than your childhood Fubu fresh tracksuit. You can break the three-piece down and wear it as separates too. And while you’re at it, maybe even trade off your Big John’s for a pair of jeans tailor made for you?

Image: The Sartorialist

We mentioned this before—suits and sneakers. Admittedly, this takes a little more thought than some of the other options but if you’re not a fan of formal footwear, it’s definitely worth experimenting with. Proper tailoring is proportionate, it’s not over sized or baggy, unless your bringing back the 1940s, so chunky sneakers aren’t something you should go for. The only exception would be New Balance as they aren’t as heavy on the padding like Nike’s LunarGlides. Plimsolls or any other sleek, slip-on silhouette is a much more effortless style to pair with tailored garments.

Image: Highsnobiety

Chinos come in many cuts and styles and by now you should have been repping the chino and sports jacket combo for years. It’s probably time to step it up a level to a pair of tailored trousers and it’s as simple as dressing exactly like you would with chinos. You really can’t fuck this one up—if there was a set of levels to learning to clean up your silhouette, this is level one. The next level would be learning to tuck your shirt in, so your legs don’t look like you stole them from your baby brother. The beauty of tailoring is that you can have your favourite fit and cut made in different fabrics. Linen or cotton for summer? Flannel and denim for winter? The options are almost endless.

Image: No Man Walks Alone

More and more people are wearing seasonal hats and although hats in general aren’t tailored, some brands are making custom or made-to-measure hats. If you’re lucky enough, you may even find a milliner hidden in your nearest alleyway. But if you’re not ready to rock the full-blown brim, you can keep it more low-key with beanies, five-panels and maybe, just maybe, you can test the waters with a fedora. Fedoras are definitely starting to see more play outside of the internet set, and beanies are the easy winter go-to. When it comes to wearing with a tailored street style the key is always balance. If you have multiple layers, a thicker beanie will work and less layers would call for a thinner beanie to give a better head-to-body ratio.

Image: Maleik Njoroge