If you follow me at all you are probably aware of my style preference: tomboy. Still feminine, but always with unexpected masculine elements to tie up the look. It makes me feel confident and most myself. The menswear-inspired fashion is always trendy, I’d say. Personally, I love to see women on the streets who wear at least one garment or accessory borrowed from the menswear section (if you haven’t seen my Youtube series What Everyone is Wearing in New York, please do). Sure, if you are a beginner to this trend, then you better start from brogues and classic menswear basics, like tailored pants, oversized blazers or outerwear (one you should really invest in!) that look unisex. Keep on scrolling to find out 5 key pieces to nail tomboy style.

Oversized Blazer

Oversized wool blazers not only offer the same allure as their cotton counterparts (the boxy, draped on the shoulders ones) but they also provide a touch of extra warmth thanks to their weightiness. It’s a win-win; style and substance. Take a look at my favourites in the carousel below.

Wool Coat / Trench coat

Temperatures are dropping and that means we all need to start dressing for mid-winter weather. That means a sturdy trench coat or a wool coat even, depending on how chilly your hometown is. Selecting your fall/winter go-to requires balancing warmth and style. Thankfully, the trend for boxy peacoats and oversized trench coats is not going anywhere. When in doubt, go for dark. If you already have plenty of navy, eye-catching shots of colour should make a good statement. Menswear outerwear will make you look cool with little to no effort, trust me.

Boyfriend Jeans

Comfort is key. Who’s with me? You can’t go wrong with a good pair of blue jeans – and I like loose-fitting boyfriend jeans in a medium wash. The slouchy and sometimes oversized silhouette is always relaxed, making them a go-to jean comfortable enough to live in day in, day out. Boyfriend, baggy jeans have got all the fixings to become your new go-to. If you’re going for that casual-cool aesthetic that earned jeans their staple spot in closets all over the world, look no further than this style. Though the general rule is that these pants are oversized in some capacity, there is a range of silhouettes, and no matter the design, the boyfriend jean is forever classic. They’re a style to keep in rotation for seasons to come, which means a good investment piece.

Oxford Shoes

The spotlight of any outfit: chunky brogues. They add an element of dimensional design, height and edginess to the otherwise casual look. Who needs a pair of heels to make a statement anyway? I certainly don’t. The sole is the edgy twist we need on such a sophisticated and classic design. Keeping in mind both comfort and style, these shoes work perfect because they meet at the intersection of formal and casual.

Tailored Pants

The art of tomboy style starts with elevating your basics. And a pair of relaxed but also refined trousers are one of the most important foundation pieces. A fine-looking pair of tailored trousers makes anything you wear look good, whether you couple them with a simple knit top like mine, a chain necklace, a chunky knit, or a pair of sneakers. For the colder months, though, it’s nice to have a couple of pairs in heavier-weight fabrics such as wool. Below you can find an edit of relaxed straight tailored pants ready to be the hero of all of your fall/winter tomboy ensembles. (Because I know you’re wondering, this bag I’m wearing is Kate Spade.)

Who else loves a good tomboy moment? Tell me in the comments!