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The Big Guy’s Guide On What To Wear To A First Date


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Whether you’re keeping it casual at a bar or looking to dress to impress, you want to make sure that you’re looking your best for your first date. And here’s the hard truth: the best ‘effortless’ looks are anything but!

But, have no fear for first date dressing because BadRhino is here to help. From a classic overshirt and jeans to a jumper and shirt combo, say hello to the big guy’s guide to what to wear on a first date.

1. Tapered Jeans, An Overshirt And A White Tee

If you’re looking for something that’s a little more casual but shows that you’ve still made an effort, then you’ll want to make sure that you’ve got an overshirt in your rotation. Whether you prefer checked patterns or block colours, you’ll steal their heart in an instant.

Plus, having a jacket with you is the perfect excuse to to be a proper gent and offer it to your date when the weather gets a little chilly during your evening walk…

Team with a pair of tapered leg trousers that help to fit and flatter bigger thighs as well as a basic white tee that you can easily dress up or down. You can thank us later!

2. Polo Shirt And Chinos

Looking great doesn’t mean you have to get so dressed up – sometimes it just means swapping your jeans for a pair of trusty chinos.

Tread the line between smart and casual and instantly elevate any first date outfit with a polo shirt and chinos combo as your new go-to. Made from a stretchy, cotton-rich fabric, these chinos are a great must-have in your date night wardrobe.

Simply finish with a polo shirt — the design and colour choice is up to you — and get ready for a great first date.

3. Smart Trousers, Smart Shirt And Boots

Now we’re stepping up. This tidy outfit is a cut above the standard ‘jeans and tees’ fayre, and best of all: it puts posh restaurants back on the menu.

Keep your look simple with smart trousers, a matching smart shirt and boots — a classic look for when you need to make a statement!

If you opt for a long-sleeve shirt, roll up those sleeves (twice, for good measure) and pop open that top button to add a little bit of a laidback vibe to this more formal look. Tuck into a rare steak in a well done outfit that your date will love!

4. Straight Leg Jeans, A Jumper And A White Shirt

Every man needs a go-to smart-casual look that he can rock for first dates and beyond.

Give your date the right first impression and opt for a jumper styled with a white shirt underneath. Complete the look with a pair of dark-wash straight-leg jeans to tone down the formal feels of the white shirt. This look is great for a dinner in the winter or over downtown cocktails.

5. Cargo Shorts, Short Sleeve T-Shirt And Trainers

If you’ve planned a first date when the warmer weather has hit, then this can make it even harder to know what you can and can’t wear.

Whether you’ve organised to do an activity or you’re simply enjoying a drink together in a beer garden, then a pair of cargo shorts are great for storing all your essentials without having to bring a jacket or backpack in tow. Finish with a pair of casual trainers and a printed t-shirt.

Style Do’s And Don’ts

When it comes to styling, there are a few things that you can keep in mind when you’re picking your first date outfit.


1. Dress For The Occasion

No matter what you’ve got planned — whether it’s drinking at a bar or taking on an escape room — make sure that you’re dressed for the occasion.

The last thing you want is to overheat with something long sleeve on if you’re moving around or not be properly dressed for if you’re heading to a posh restaurant!

2. Feel Confident In What You Wear

The most important thing is that you feel comfortable in what you wear. If you’ve never worn shorts or prefer to stick to oversized styles, then stick to what you know.

If you’re not feeling comfortable in what you’re wearing, then this will show through to your date.

3. Opt For A More Neutral Colour Palette

Understated and muted colours keeps your look sophisticated. Think black, navy, grey and white tones when you’re putting together your look.

A brighter colour is great thrown in here and there, but try not to make your whole outfit a bold and bright red or an overbearing pink.

4. Add A Splash Of Aftershave

Smelling good is just as important as dressing right. A simple spray of your favourite aftershave can go a long way. But remember, don’t go too crazy and overpower your date with the smell!


1. Wear Open-Toed Shoes

This one is self-explanatory but open-toed shoes are a no-go for a first date. Even if the date is super casual or the weather is warm, then just stick to trainers. Please.

2. Opt For A Tie

First dates should be about making both yourself and your date feel comfortable. Ties can come across as a bit serious and can make you feel stuffy — especially if you’re in a place that’s warm! Even if you’re meeting your date somewhere dressy, a simple pair of smart trousers and a smart shirt can do wonders.

3. Wear A Hoodie

Hoodies are a great option if you’re lounging around at home but not if you’re heading on a first date. Sweatshirts are a great compromise if you’re looking for a piece that you can dress up or down.

4. Over Accessorise

You know what they say: less is more! Keep your accessories simple — think watches and sunglasses if need be — just don’t go over the top with flashy jewellery.

Shop more must-have big and tall clothing in sizes M-8XL.

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