June 29, 2016

Headgear is a tricky thing, especially in Singapore, where confining your forehead to hair in a tiny, ventilation-deprived space isn’t exactly weather-permitting. And yet, so many have been able to adamantly rock headgear trends through the years, taking us from trucker hats to beanies and everything in between. So in proud support of those who dared to sweat for style, we take a look at the evolution of caps and hats through the years (specifically the fashion-confused 2000s).


Early 2000s: Trucker hats

Screen Shot 2016-06-29 at 5.33.29 PM Screen Shot 2016-06-29 at 5.35.26 PM

Images from YouTube

A truly terrifying trend primarily involving brands like Von Dutch and Vans, the boxy, boyish, mesh-backed baseball cap probably owes its fame to Paris Hilton during her The Simple Life years. The look spread like wildfire across celebrities and plebs alike, and unfortunately even made its way onto our shores for a good few years. We thought we’d seen the last of it before the turn of the decade, but more recently, a certain youngest Jenner has resurfaced it as a possible comeback. Dear Lord, say it isn’t so.


2006 – 2009: Beanies

One of the most unwearable options in Singapore; yet even we were guilty of rocking the occasional knitted beanie back in the mid 2000s. Bloggers and celebrities were often spotted tossing on a casual floppy beanie to complete their street-style ensembles, and fast fashion retailers churned out, by the dozen, everything from short “rapper-approved” hats to daintier, beret-inspired beanies – you know, the kind that covered your ears comfortably and chicly.


2009 – early 2011: Snapbacks


New Era New York Yankees Purple Logo Black 9fifty Snapback, $65 

Less obnoxious than the trucker hat, but frankly just as bad. Snapbacks come with a distinct pop-open adjustable strap at the back, so one size can truly fit all. Another telling feature to tell the two apart is the coloured inner bill (ie. the brim) on a snapback, which usually comes in a bright, garish colour separate from the rest of the cap. A particular hot favourite amongst our teenagers and secondary school kids, especially knockoffs of the now infamous New York Yankees cap, and OBEY.


2011 – 2013: Floppy hats

Screen Shot 2016-06-29 at 6.45.01 PM

Image from Instagram (@imjennim)

Another trend courtesy of bloggers! Or to be more specific – fashion bloggers, Instagrammers, and influencers, given the sudden rapid transition from to Instagram over this time. They come in a variety of colours and materials, but the dramatic floppy shape remains consistent. We’ll admit, these aren’t the most practical to don anywhere but Europe; but there’s also no denying how effortlessly chic a classic black velvet hat looks. They’re still circling the market right now, so don’t be afraid to pick one up for your next holiday.


2013 – early 2015: Bucket hats

Kinda cute, but these left us really confused for the most part. Predominantly worn by hipsters, goths, and anyone who went to Laneway.


Late 2015 – present: Dad caps

m30630_fr_ecom GWPink2

Adidas, Anti Social Social Club

Enter the present, and fashion is finally doing it right! We actually really dig today’s evolved version of the simple baseball cap; the “dad cap” is essentially a baseball cap, but slouchier and less structured, for a more relaxed, off-duty vibe. They’ve definitely been making their rounds on Instagram, but with good reason – they nail effortless casual while being actually comfy. Sports brands like Adidas and Nike have been quick to capitalise on it and establish themselves as icons of the classic dad cap, but if you prefer something a little more alternative, a host of indie vintage brands await you too – like the permanently sold out AntiSocial Social Club, for one.