A Woman’s Guide to Menswear-Inspired Style: Key Pieces and Styling Tips

Oversized clothing has taken the fashion world by storm in the last few years, from giant sweatshirts and t-shirts to oversized blazers and loose wide-leg trousers. Not only is our leisurewear getting larger, but so is our office attire. This trend is continuing to gain popularity because of its versatility to wear with other styles and because it is extremely inclusive, it looks good on pretty much any shape or size.

This year fashion designers continue to include oversized blazers and wide-leg trousers in their lines and the term ‘Preppy’ has been thrown into the mix. Unlike the preppy Ralph Lauren polo shirts of your youth, this new version is extremely sophisticated. They’ve taken inspiration from classic and vintage women’s fashions such as crisp white shirts, pearl button-down cardigans, A-line skirts and your favourite oversized blazer to complete this fashion-forward look.

woman wearing oversized trench coat
The trench coat is a classic example of mens styles in women’s oversized fashion

Although oversized leisurewear will always have a place in our wardrobe we can expect to see a move towards this more refined style through the autumn and winter months. I love this move back to vintage fashions, the classic silhouettes together with more modern styles are fun, yet feminine and feel easy to pull off with just a few key items.

So what exactly are these items and how can you add them to your existing wardrobe, let me show you how.

woman wearing overzised suit
oversized jackets and blazers are ideal for layering

Oversized Blazers & Jackets

The way we’ve worn oversized blazers has changed many times. Last year you might have worn one with fitted cycling shorts, this Autumn you’ll wear them with short mini skirts, floaty boho dresses or long wide-leg trousers.

Oversized blazers have a powerful masculine vibe that pairs perfectly with soft feminine styles such as skirts or dresses. If you want to appear more casual wear one with a crisp white tee and a fun tartan mini skirt. For the office combine them with a white shirt or ruffled blouse and oversized trousers or an A-line skirt. The versatility of this style makes it ideal for every body type and easier to mix and match outfits as you want.

This year tartan and tweed are more popular and warmer over the winter months so investing in an oversized tweed jacket will be worth it and easy to accessorise with. Large chunky scarfs, belts and burgundy handbags all work well with this look.

It may remind you a little of your nan but it’s exactly this vintage style that’s making a comeback and there are some amazing bargains to be found in vintage shops.

wide legged trousers style
Wide-legged trousers are a great oversized look

Wide-leg trousers and a Ruffled Blouse

Meghan Markle has made super long wide-leg trousers her go-to style and it’s easy to see why. On their own they look masculine but worn with a fitted top or a feminine ruffled blouse they appear softer and elongate your body.

The long drapey fabric will make you look taller and slimmer and can be worn from the office to the bar afterwards. Mixing them with a top that has ruffles, delicate lace or embroidery is a great way to showcase your feminine side whilst embracing this masculine look.

When you buy a pair of wide-leg trousers, focus on a few key items:

  • Choose high-waisted – This will make your waist appear slimmer, and lengthen your legs.
  • Consider cropped wide-legs – Taller girls will be able to pull this look off better, or wear it with heels if you are shorter.
  • Look for men’s wear fabric – focus on materials like tweed or herringbone that will drape well and stand out against a fitted top.
  • Shirts and High-Waisted Shorts

If you are not sure long wide-leg trousers are your thing then a pair of high-waisted shorts may be better. Crisp shirts and suit-style shorts in natural colours are fun and sexy. By letting your legs do all the talking you can wear a simple top half and still look understated yet classy.

Khaki is making a comeback this fall and would give your shorts a military feel, so think vintage 50s and wear them with t-bar heels and a fitted top for a striking combination. If you’re wearing them to the office neutral ballet flats and a matching oversized blazer will work better and are an interesting alternative to a skirt.

Again the high-waisted element will slim down your waist and the short length will accentuate and lengthen your legs which is great if you are on the shorter side like me. This look also works well with a belt, especially one with a gold buckle to draw attention to your waist.

oversized blouse and skirt
You can pull of a vintage style with a blouse

Oversized Button-Up Shirt and Belted Waist

Ah the classic white shirt, we all have one right? Well they never really go out of style which is great because it can be worn in countless ways. A fitted shirt works well with trousers but sometimes you just need something a little different.

An oversized shirt reminds me of vintage fashion and I can imagine wearing one with chinos and ballet flats like housewives from back in the ’60s. They’re not fussy or fancy but worn with a blazer and smart handbag and suddenly you are modern, super stylish and sophisticated.

If you want to change it up even more a belted waist will take your shirt from boring to impressive. For an evening out you could wear it with a gorgeous silk skirt in khaki or black.

Think quiet luxury; golds, pearls and expensive-looking handbags which will complete your ‘debutant’ outfit. This is another trend you want to watch out for and is doing the rounds on the catwalk.

ladies wear tweed
Tweed is always a good winter option

Tweed Mini Skirt and Boyfriend Blazer

Mini skirts and boyfriend blazers go together perfectly. With 90s fashions heavily influencing us right now it was inevitable that tartan and tweed mini-skirts would be reappearing too. Take some inspiration from films like Legally Blond and Clueless and be brave with different colours and textures.

Kitten heels and platforms will always look good with this style but for a modern take that’s a little more sophisticated than sexy, I would wear mine with some tall structured boots and an oversized handbag. It can be a fine line between understated and too much.

Classic White Button-Up and A-Line Skirt

This perfect pairing is very much in line with the Preppy trend around at the moment. There were numerous versions of this on the catwalks this year but mostly the shirts and skirts were worn with tall boots and oversized jackets.

This is a classic combo that would be suitable for many occasions so I would play around with different colours and patterns to make it more interesting. Perhaps a brightly coloured blazer on top or make your skirt bold with a floral pattern or Leopard print if you really want to be on trend.

a line skirt and blouse

Waistcoats

Smart tailored clothes always work well with more casual pieces and a masculine waistcoat is one way to achieve this chic look. To be honest you can’t go wrong with a waistcoat they will complement nearly any outfit. Celebrities around the world have been wearing them to film festivals, premiers and parties.

They are the perfect option for layering as you can wear them open over shirts or t-shirts or wear them on their own with a blazer or jacket over the top. For a casual look wear them with a pair of jeans or dress them up with suit trousers or a maxi skirt for the evening. I would stay away from brightly coloured or patterned versions as they are a little reminiscent of your great uncle Bertie, but neutrals or monotone shades will complement most colours in your wardrobe.

Conclusion

Menswear-inspired clothing has become a fashion staple and continues to shape new trends, not many of us could imagine that the humble waistcoat would become the epitome of fashion once again. The great thing about this trend is its versatility, there are endless combinations you can achieve with just a white shirt, blazer and wide-leg trousers.

It’s accessible to women of all shapes and sizes and actually flattering. Not only is it super chic it’s also fun and sophisticated, no one does strong, independent woman better than one wearing a man’s blazer.

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Chloé Safilo
Chloé Saffio is our resident Fast Fashion Expert for the UK Urban and Streetwear scene. Her eyes have been constantly glued to social media for the last 10 years giving her an unrivalled insight. In her spare time, she used to like shopping and lying in the sunshine and making the pilgrimage to Ibiza. Now, she is a tired and grumpy new mother and back from maternity leave as the full time FFN writer. Chloe lives in London where she completed her journalism degree at the University of Roehampton. She lives in a small flat Putney with her fiancée Christian, daughter Sofia, and their French Bulldog Coco. And she's on the look out for a nice house and garden at a bargain price,