As we enter this transitional season it can be difficult to know how to accessorise our looks in a way that keeps us looking on-trend but also feeling appropriate for the change in weather. So we put our thinking caps on at Sloanie HQ and came up with a quick go-to style guide for the preppiest headwear options out there as we move from summer through to fall. 

Baseball Cap


Daily Mail

The ideal preppy accessory for your laid-back daytime look for summer sun and crisp fall days, the humble baseball cap looks best a little beat up in our opinion. Choose a trucker style for a more urban, hip hop look (think Cara Delevingne, Rihanna and Rita Ora) – or a good old fashioned baseball cap, sporting your team crest of course, for an altogether preppier style. Great for hiding a bad hair day or an unbrushed barnet on the way home from the gym or yoga studio, we love the tomboy style that model Alessandra Ambrosio is rocking here, and you’ll see below that baseball caps get the royal seal of approval too: K-Middy’s a big fan, and so are we!



Felt Fedora


Cooler weather brings with it a whole host of cosy cover-up options, and Brit model Rosie Huntington-Whitely is a big, big fan of the felt fedora. The fedora can be boho or super smart depending on how you style it, and looks as much at home at Glastonbury as it does Bond Street or Sloane Square. Fedoras also came out in force at Royal Ascot this summer, in stark contrast to the event’s profusion of elaborate hats and fascinators. Above, Rosie’s gorgeous plum colored felt accessory gives her sleek airport arrival a cosy fall update that doesn’t scrimp on preppy style one bit. Just gorgeous. Her look below exemplifies this perfectly in her chic camel coloured felt hat, Burberry Prorsum monogrammed blanket poncho and knee high Louboutins.  RH-W, we absolutely adore.


Cossack Hat

Faux-fur alternatives available and advised, the furry Cossack hat looks stunning on winter shoots in the English countryside, best paired with simple pearl stud earrings and rosy cheeks from all that fresh air. Pippa Middleton wore hers to Cheltenham Festival last springtime, and positively oozed Sloanie style with her oversize sunnies and statement dress coat. Sister Kate rocked hers seven years earlier, proving the longevity of this particular trend. But you needn’t be all dressed up like a Middleton to sport one of these cosy headpieces – they look great with a Barbour jacket and wellies, bringing a dash of glamour to the field on chilly countryside weekends.


Hello Magazine


Tell us about your can’t-live-without hat by dropping us a comment below. Or why not take a selfie and post it to Instagram using the #SloaneRanger #SloanieHats hashtags? We’ll look out for you on there and regram our faves.


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  • Sloanie dearest,
    You haven’t written anything in ages! I always look forward to reading your posts, and you’ve kept us all waiting quite some time. Please do post soon.
    Plaid Is My Favourite Colour