The Big Guys Guide to Dating

After weeks, months or years since your last date, it’s finally come along! Soon you’ll be spending time in their company, enjoying good food (with wine of course) and moving onto whatever else you may have planned. If you’re here, you’re probably wondering what you should be wearing and as a big guy want to know what looks best, so read on for our top tips and ideas for what big guys should wear on a first date.

What Should Big Guys Wear on a First Date?

Of course what you decide to wear on a date is completely up to you, but we have compiled three different looks, which cover a range of activities and (hopefully) offer you some style inspiration.

Dress to Impress

If you’re off on a formal date, maybe to a fancy restaurant, the theatre or looking at spending the night at a bar, look cool smart and sophisticated in a modern suit. As well as being one of the most slimming outfits available, suits are great for showing off your sense of style. Suits are also really easy to inject a bit of personality into with bright patterned shirts and accessories whether that’s a pocket square, tie or a pair of fun socks! If you’re looking for a bit more information on suits, check out our suits guide for larger guys! It’s got loads of tips and styling advice to help you look your best.

What Should Big Guys Wear on a First Date? - Dress to Impress with a SuitBest for: A fancy date – think three course meals, watching a musical at the theatre, a trip on a boat – you get the idea.

Shop the look:

Hugo James Hazan Suit in Navy
Kariban Long Sleeve Oxford Shirt
POD Dallas Tan Shoes

Cool and Casual

If your date is more of an informal affair like a quick coffee or something fun – maybe a round of mini golf, before a stroll along the beach, a casual outfit is the way to go. However, keep it smart too. A pair of baggy jeans and a funny print T-shirt probably won’t go down too well so instead pair some straight, dark indigo jeans with a check shirt or polo shirt for a cool and casual look.

What SHould Big Guys Wear on a Date - Play it Cool and CasualBest for: Shorter dates like a quick coffee or lunch date

Shop the Look:

Espionage Medallion Print Shirt
Le Breve Leroy Jean
Roamers Black Suede Desert Boot

Comfortable, but Stylish

Spending the day with your date? Comfort is key. There is nothing worse than being uncomfortable with what you are wearing. Whether that is because you’re too hot, your trousers keep falling down or the outfit just isn’t ‘you’. Ultimately, you’ll be spending the whole day with this person and you don’t really want to be thinking about your trousers falling down or your buttons popping open. So, what to wear. Whether you are going to a theme park or visiting a national trust site, dress comfortably by pairing a decent pair of jeans with a belt, some comfy shoes and a short sleeve shirt or nice tee.

What Should Big Guys Wear on a First Date? Remember to stay comfortble and stylish Best for: All day dates

Shop the Look:

Kangol Stott T-Shirt in Grey
Raphael Valencino Indigo Jeans RV4
Front Reef Canvas Lace Up Trainers in Grey

So there you have it, three different looks for three types of first date. However, no matter what you decide to wear, don’t change who you are and remember that confidence is one of the sexiest things you can wear.


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