Tip of the Hat: Decoding a Guy’s First Date Accessories

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There’s nothing quite like first date butterflies – you wonder what kind of spark there will be, pray that you don’t spill food on yourself and spend hours meticulously primping. But for all that time spent getting yourself mentally and physically prepared, don’t forget to take a hard look at what your man is wearing on a first date – even his choice of accessories can convey a distinct message about his personality.

As a fashionista and the community manager for Loveawake, the premier online community for singles, I know about the importance of a proper first date wardrobe. I’m here to help you read between the lines – or paisley or plaid – to learn whether he’s second date material or just a fling.

Hats: Obviously there are far too many types of hats to make a sweeping generalization. Though hats are a distinct way for a guy to show his personality, they can sometimes scream for too much attention on a first date. Venues where a hat is OK: outdoor sporting event (baseball cap), speakeasy (fedora), poetry slam (beret), skiing (beanie) or monster truck rally (trucker hat).

Nice watch: Some guys’ idea of a “nice” watch is simply that it ticks and doesn’t have a superhero on it. If your man flashes a classy timepiece, it shows he is traditional and wants to put his best foot forward.

Scarf: In spring and summer: Prissy. You’ll probably have to put your coat down for him to cross a puddle. In winter: Mature. It takes a big man to admit he’s cold.

Sunglasses: He thinks he’s too cool for school. It’s important to look into your date’s eyes when you’re getting to know them, and let’s face it, it’s not like he had to dodge a crowd of paparazzi on his way to meet you. Occasion where sunglasses are OK on a date: You’re outside and squinting uncomfortably to see your love interest.

Cufflinks: Let me just wipe my drool… ah yes, cufflinks – they show ambition. Not a lot of guys own them, even if dress wear requires them. They’re truly an investment piece, and show he cares about his appearance and where he’s going in life.

Umbrella: Meticulous. If he thought to check the weather before your date and made the effort to lug an umbrella with him, he’s clearly a planner – and a keeper! Added bonus: there’s room for two under that umbrella.

Suspenders: He thinks he’s unique. Unless he’s Steve Urkel, suspenders are a guy’s way of showing how “different” and cool he is. He’ll try to sell you a story about how he found these ol’ suspenders at a thrift store in Williamsburg, but trust me, he spent $500 to look that vintage.

Bracelet: Sentimental. Do you know any men who wear bracelets that don’t have some sort of significant emotional meaning? Ask him about it as an icebreaker and get to know what makes him tick.

The bottom line is that you have to give any man points for accessorizing – it’s so much easier to just throw on a shirt and jeans rather than go that extra mile. When a guy puts in the effort, take notice of these non-verbal cues to see if he could be your perfect match.