How To Wear A Flat Cap: Three Looks To Ace Autumn

by Welcome to Outsons
Wear A Flat Cap

Don’t know your driving cap from your baker boy? 

Whether it’s the Peaky Blinders style Newsboy cap you’ve got in mind, or even a sleeker ivy cap, a flat cap style hat is the must have autumn accessory. Luckily this hat comes in a range of designs and is incredibly flattering on all face shapes, meaning you’ll easily find the perfect one for you.

What To Wear Your Flat Cap With

The real challenge with a flat cap is what to wear it with. You don’t want to look like you’ve stepped off the set of a costume drama (though you can take some style inspiration from Tommy Shelby…) but equally anything too casual will do a disservice to the traditional roots of the flat cap – if you pair your flat cap with a t-shirt and sliders, the fashion police may be called. Just saying. Luckily our style guide has three amazing autumn looks to keep your head warm that any guy can pull off. Here’s how to wear a flat cap: 

1. The Smart Outwear Look

A firm favourite amongst men’s style icons like David Gandy and David Beckham, the tweed newsboy cap is one of the more popular flat cap styles worn today. This is partly thanks to Peaky Blinders, which reintroduced the nation to the smart versatility of the hat. Go for a  newsboy cap in a herringbone tweed, but make sure to wear the hat with a wool coat made in a contrasting colour and weave. If you get this right, you’ll avoid looking like you’ve dressed up for a ‘20s party and keep your outfit distinctly 2020. To complete your ensemble, wear a soft scarf undone beneath your coat. This will create added texture and is an effortless way to bring some colour to your flat cap fashion. We particularly love a merino scarf in an olive green, a colour which will suit all skin tones. 

The Smart Outwear Look
Image Credit: @davidgandy_official via Instagram

2. The Creative Utility Look

While we may now associate this hat with a more dressed up look, for most of the 20th century men would wear a flat cap as part of their day-to-day work clothes. This means that nowadays flat caps still look perfectly at home when styled with utility workwear and are great for creative men who want to show off their artistic side. Whether it’s a flat driving cap, or a looser newsboy hat, you can wear a flat cap of any style with a blue utility jacket that will feel at home in the studio and at those after work drinks. Go for a plain t-shirt underneath to keep the look simple and avoid creating a messy neckline. To honour the utility look, you should wear your hat and jacket with a pair of rigid workman’s jeans that have some stiffness to the denim. This versatile look will work well with both trainers or brogue boots for the perfect autumnal outfit.

The Creative Utility Look
Image Credit: @brixton via Instagram

3. The Vintage Bohemian Look

The beauty of these hats is that, as the style has been worn for so many years, flat caps go with a real range of vintage looks. Men’s bohemian fashion uses soft fabrics and layered accessories to capture the essence of curiosity and wanderlust that artists and free-thinkers embody. Flat caps are an easy addition to bohemian attire and will give your outfit a timeless vintage feel. You can’t go wrong with a cap in a light grey with a soft blue chambray style shirt. Wear with a red bandana (an essential bohemian accessory) and tapered cotton trousers. If the weather is chilly, just add a jumper in a loose knit or a soft roomy cardigan. We like this look worn with some smart braces, but just be wary about straying too far into vintage dress up – your cap will give you a timeless feel as is.

What To Remember When Wearing A Flat Cap

Now you know how to wear a cap as part of a balanced outfit, there’s a few more things to consider when choosing the perfect one for you. The most important part of finding the right hat is to get the correct hat size. You can do this by measuring the circumference of your head with a tape measure (the floppy kind, not one from your DIY box). If you don’t have a tape measure use a piece of string and then measure that length against a ruler. If you get the wrong size your flat cap will either sit too high on your head or will tilt too far down your face. 

5 Best Flat Caps You Can Buy Right Now

As well as the three impressive hats we’ve already brought you, here’s five of the best flat caps you can buy right now:

1. Kangol Tropic Spitfire Cap In Black

2. Brunello Cucinelli Corduroy Flat Cap

3. Dolce And Gabbana Velvet Flat Cap

4. Tagliatore Plaid Flat Cap

5. Dsquared2 Wool Flat Cap

Alternatives To Flat Caps

So you prefer something more modern when it comes to men’s fashion? Flat cap aside, there are plenty of choices when finding your perfect hat. If you’re here looking for a hat that will keep the sun out of your eyes and hide any bad hair days, you might be surprised by just how stylish a baseball cap can be. Gracing the heads of Hollywood A-listers and urban creatives alike, baseball caps can be pulled off by any guy. Just make sure you check out our guide on how to effortlessly wear a baseball cap and your hat game will be on point.

Feature image: Dollar Gill

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