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Will You Be My Best Man? 34 Brilliant Ways to Ask Your Mate

Whether you’re playing it cool or planning a dramatic proposal, here are some seriously creative ways to ask your best mate to be your best man, many of which you definitely won’t have thought of…

Man in checked suit adjusting his best man's buttonhole

The ‘will you be my best man?’ chat can actually be pretty nerve-racking as conversations with your best mate go. You know that the answer is almost certainly ‘yes’, but you still want to impress your pal and mark the moment. Handily, we’ve done the hard work for you in terms of ‘will you be my best man?’ ideas – you just need to pick one that’s personal to the man in question and that reflects your relationship. 

It could be that you’re planning a ‘bromantic’ pre-wedding bike trip, love nothing more than enjoying a dram together or are both cheese fiends – whatever your vibe, there’s a best man proposal gift to suit, plus card ideas aplenty to get your feelings down on paper. You want to get him onside now before he starts working on his speech, after all. These ‘will you be my best man?’ suggestions should do just that…

NB: We have included third party products to help you navigate and enjoy life’s biggest moments. Purchases made through links on this page may earn us a commission.

‘Will You Be My Best Man?’ Gift Ideas

1. The Best Man Personalised Print – £25, Just For You

Personalised silhouette movie poster style art print reading The Best Man

Do best man proposals get more cinematic? We think not. Make him the star of your show by giving him this movie style art print and your intentions will be crystal clear.

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2. Personalised 'My Perfect Best Man' Print – £35, Wordplay Design 

Colourful word based art print featuring customised phrases, places and dates

Same kind of idea, just with more scope for in-jokes. Customise this colourful print to suit your best man-to-be and remind him of the awesome times you’ve had. 

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3. Gilded Monogram Glass – £14, Anthropologie

Collection of clear tumblers with different letters etched on in gold

If you prefer a more subtle style of personalisation, this cool gilded glass will fit the bill. You’ll just need something to pour into it for the proposal...

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4. Islay Single Malt – £55 for 70cl, Fortnum & Mason

Bottle of single malt Islay Scotch whisky with two etched whisky glasses

Smokey and creamy with a distinct hint of a sea breeze, this fine single malt will go down a treat when popping the ‘will you be my best man?’ question. Roaring log fire optional.

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READ MORE: A Complete Guide to Best Man Duties

5. Build Your Own Gift Box for Him – from £18, The Tartan Blanket Co

Picture of man from behind wearing a navy backpack with a neutral tartan blanket rolled at the top

Sticking with the Scottish vibes, you can make this DIY box as minimalist or luxurious as you fancy with the choice of lambswool or cashmere tartan scarves or blankets with the option of adding everything from socks to soap to snacks to mugs (and more). If you’re planning a Scottish wedding it’ll have even more impact. 

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6. Personalised Portable Camping Fire Pit – £69, Oakdene Designs 

Man putting a burger onto personalised metal campfire that's cooking chicken kebabs

Snuggle by the fire or get some steaks on the barbie and ask him to be your best man by way of a personalised fire pit. Weekend away optional. 

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7. Personalised Blue Insulated Cooler Backpack – £14.99, Hitched Shop

Royal blue cool bag backpack with initials stitched in black onto the front flap

The coolest take on a cool bag we ever did see, this insulated backpack is ideal attire for stag dos and the office alike. His initials can be embroidered in a wide array of shades and fonts, so have fun with that. 

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8. The Essentials Mixed Beer Case – £35.99, FarmDrop

12 beers in cans and bottles displayed on a marble counter

These 12 beers are just begging to be added to that cool bag and they’ll make for something more interesting than your average six pack. 

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9. Hot & Spicy Letterbox Charcuterie – £30, The Real Cure

Selection of cured meats, cheese, olives and cocktail sticks displayed on a wooden table

The perfect accompaniment to a few beers after you’ve asked him to be your best man (he'll need them to cool off after sampling this spicy salami selection). 

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10. The Penguin Book of Modern Speeches – £14.99, Oliver Bonas 

The Penguin Book of Modern Speeches in white and orange design with an illustration of Obama on the cover

Handing this book over might give the game away in itself but be sure to follow up with the big question and a feeler as to whether you’re expecting Obama-level speech skills. At least he can swot up if you’re setting the bar high.

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READ MORE: 21 Best Man Toast Ideas to End His Speech

11. ‘Will You Be My Best Man?’ Telegram – £14, Imperial Telegrams

Two vintage telegrams with retro stamps and a personal note

Correspondence with your best man doesn’t get more old-skool than via telegram. Custom made featuring vintage stamps, he’ll feel honoured when this drops onto the doormat. 

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12. Personalised Silver Mechanical Pocket Watch & Fob with Diamond Emblem Monogram – £39.99, Hitched Shop

Man in a suit holding a silver Art Deco style pocket watch engraved with the initial M

Equally classic, this art-deco style engraved silver pocket watch is a snappy addition to any suit and will encourage him to be bang on time on your wedding day. 

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13. Kingsman + Drake’s Silk Pocket Square – £55, Mr Porter

Close up of a dark grey suit with a burgundy silk pocket square

Speaking of snappy suiting, this handmade silk pocket square is as dapper as they come. Present him with this when you ask him to be your best man and you won’t have to consider groomsmen colourways at a later date either. 

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14. A Tie – from £10, T.M. Lewin 

Assortment of different coloured ties secured together with an orange tie in the shape of a bow

If you’ve decided on your wedding suit styling, kit him out early by giving him a tie when you pop the question. 

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15. Brushed Rectangular Cufflinks – £15.99, Hitched Shop 

Close up of a man securing a silver monogrammed cuff link onto a white shirt

You may as well go the whole hog – sleek and understated monogrammed cuff links will go with every suit and shirt combo and become a go-to for decades to come. He’ll think of you everytime he gets all dressed up.

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16. Bespoke Wedding Socks – from £12, The London Sock Company

Gift box containing a pair of bright pink socks with a note to a best man

Select a sock style, shade, and gift package of choice and send this to your mate alongside a handwritten note asking him to be your best man. It might just be the first he’s shed a tear over socks. 

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17. Tom Ford Neroli Portofino Conditioning Beard Oil – £46, Selfridges

Tom Ford conditioning beard oil

Give him the gift of a glossy beard when you ask him to be your best man and he’ll thank you for months. A tiny dab of this conditioning beard oil goes a long way and it’ll make wedding day grooming a dream.

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18. Personalised Hip Flask – £25, Dust and Things

A man in a suit holding a personalised brown hipflask in both hands

A quintessential groomsman gift, a bespoke hip flask will deliver a little pre-best man speech Dutch courage (just make it a nip). 

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READ MORE: The Best Groomsmen Gift Ideas for Every Budget

19. Spreadable Whisky Single Malt Marmalade – £9.99, Firebox

Jar of spreadable whisky

Potentially a safer bet on your wedding morning, this single malt marmalade is the perfect present for a whisky loving best man. 

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20. Cheese of the Month Selection – £45.50, Neal’s Yard Dairy 

Slab of slate on a navy tablecloth with four different cheeses and a sharp knife

Seasonal cheese straight to his door is sure to make the prospect of being your best man even more irresistible. 

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21. Modena Diamond Blue Photo Frame – £16, Oliver Bonas

Geometric diamond blue, gold and white photo frame

A geometric diamond mantelpiece staple for a diamond guy – put a photo of the both of you in the frame before you ask him to stand by you on your wedding day. 

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22. Leather Credit Card Holder Wallet – £30, Vida Vida

Man opening a brown leather card holder embossed with initials in gold

An elegant leather gift that’ll look better with time, like the both of you really. Hot press his initials on in gold for a classy ‘will you be my best man’ gesture. 

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23. Lonely Planet’s Epic Bike Rides of The World – £24.99, Oliver Bonas

Lonely Planet Epic Bike Rides of the World book

Whether as stag do inspo or simply to help plan a trip away with your soon-to-be best man, this is a must on any cyclist’s bookshelf

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24. Charbonnel et Walker Mini Heart Dark Chocolate and Sea Salt Caramel Truffles – £6.50, Liberty London

Baby blue heart shaped box of Charbonnel et Walker dark caramel and sea salt truffles

A sentimental (and tasty) token to accompany your best man proposal. Who can say no to these dark chocolate and sweet and salty liquid caramel chocolates, not to mention the chance to rep your best pal on the biggest day of his life?

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‘Will You Be My Best Man?’ Card Ideas

Personalised ‘Will You Be My Best Man?’ Cards

25. Scratchcard – £4.95, Chips & Sprinkles

Pale blue card with a scratch off silver balloon and personalised message asking will you be my best man

Scratchcards always have an edge of excitement and this one even more so. Add your best man’s name and choose between a grey, pink or blue balloon to really put his mark on it.

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26. Best Man Card – From £3.06, Foxes On Boxes

Best man card with illustration

Simple, meaningful and sure to be a keeper long beyond the day, this illustrated card can be tailored to your heart’s desire, from the details of your groomsman to the printed message inside.

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READ MORE: How to Write a Short Best Man’s Speech

Stylish ‘Will You Be My Best Man?’ Cards

27. Chalkboard ‘Will You Be My Best Man?’ Card – £3, Norma & Dorothy

Chalkboard style card with the title will you be my best man

The writing’s on the wall/chalkboard with this one. The textured card and brown envelope make it feel more formal too. 

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28. ‘Will You Be My Best Man?’ Calligraphy Card – £2, Sarah Burns Prints

White card with a will you be my best man message written in calligraphy style writing

An affordable yet expensive looking card, you can tailor both the shade of the script and the envelope to suit your wedding theme.

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29. Top Job Best Man Card – £2.80, Joanne Hawker 

White card with top job for a top man slogan written on the front

Like a best mate appraisal, this card will convey exactly what your best man means to you in no uncertain terms. 

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30. Secret Message 'Will You Be My Best Man?' Card – £4.50, Here’s To Us

White card with a black envelope on the front containing a note asking will you be my best man

Why limit your best man to one envelope opening experience when you could give him two? This secret message card prolongs the excitement. 

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31. Simple 'Will You Be My Best Man?' Card – £3.50, Too Wordy

White card with a will you be my best man message written in black brushstroke lettering

Contemporary hand lettering makes this elegant card stand out. If he’s a straightforward guy in the style stakes, he’ll love this one. 

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32. The Gentleman Notecards – £20 for 10, Papier

White notecard with a header featuring a man's name, a top hat, a bow tie and two umbrellas crossing over one another

Fancy and yet understated at the same time, tailoring notecards and writing your ‘will you be my best man?’ message by hand is a choice move, plus you can send notecards to everyone from other groomsmen to colleagues when you buy a set. 

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Funny ‘Will You Be My Best Man?’ Cards

33. You’d Rock It In a Suit’ Card – £3.50, Wordplay Designs 

Funny card implying that the best man won't look as good as the groom in a suit

A little bit tongue in cheek, your best man will be all smiles after receiving this fun card in the post.

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34. Simply The Best Card – £3.50, Poppy’s Papercuts at Papier 

Black and white line drawn card with an image of Tina Turner and a simply the best message

Serenade him via this Tina Turner card – he’s about to be simply the Best Man after all. 

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Wondering how to get your father involved in your wedding planning too? Read our guide to father-of-the-groom duties.