
Mankind has been marking his initials on things for, oh, 2600 years or so. In ancient Rome and Greece, rulers would issue coins with their monograms as a way of staking claim to the area they ruled. Flash forward a few millennia to the Middle Ages, when kings, generals and artists used monograms in a similar fashion. Today, a groom can honor the power his friends have had on his life by giving a monogrammed gift, such as a polo or t-shirt, in advance of the big day. You’ll have your choice of size, color and type style. (A quick note on the pricing below: These are for full-priced items, but you can save on virtually all of these items by watching for sales, signing up for email lists, etc.)
For the guy who appreciates a legacy

The best-known polo shirt for nearly 50 years running, and one of the most dynamic monogram offerings around. Choose from a range of fits and materials, not to mention dozens of stitch colors and typefaces. (Gothic 3 in Purple Rage, anyone?) You or your groomsmen aren’t monogram guys? Pay tribute to a favorite pup or pastime with the brand’s ample dog, bear, and crest embroidery options. (Also, why are you reading this article?)
For the one who needs to widen his color palette

With more than 50 color options, the Lacoste polo is a style icon unto itself. Make it yours (and your fellas’) with a monogram, and you can also move around that little crocodile. Note that you can monogram up to four letters (on the sleeve, that is), instead of the usual three, which certainly puts some rather interesting words on the table…
For the guy who values versatility over brand name

An affordable and versatile choice, with a two fit options (in stretch fabric) and a wide range of colors, too. Personalize it with a monogram, embroidery, or both. If you go with the latter, you’ll have 176 logos to choose from, including patriotic ones (like American flags), quirky ones (like lobsters) and ones you will never, ever choose, but we couldn’t let pass without mention (unicorns).
For the one with a lot of groomsmen

This Austin-based brand, co-owned by Luke Wilson, offers a fun vibe, with shirt styles named after actors and movie golfers (“Spruce Willis”). Known for The Players’ Shirt, and their overall 19th hole-minded approach to golf-adjacent style. You can’t monogram a one-off shirt, but you can get custom shirts via a group order. Pro tip: If the bachelor party takes you to Austin, the brand’s clubhouse is a must-stop.
For the guy who goes by his last name

This super-breathable polo can be monogrammed with your initials, or your full name (up to 10 characters), and they do it by hand in Maine. Bonus: Available in regular and tall sizes, because we all have that friend we ironically call Shorty.
For the one who likes a lot of options

The preppy staple’s monogram offering stands out by allowing you to put your John Hancock (or rather, your J.H.) wherever you’d like, with six options to choose from. A healthy 40 color options, in three different fits, await your decision. Oh, and they also have a monogrammable garment-dyed t-shirt for $25.
For the one who appreciates simplicity

The brand has long specialized in basics, and getting a shirt monogrammed online doesn’t get much simpler than it is at J.Crew. Get one of the brand’s signature pique polos, and add the guys’ initials in one of 18 colors, and you just guaranteed your wedding party will look a little cooler at the bachelor party.
For the guy who's always on the go

The outdoor specialists make a super-soft Peruvian cotton polo shirt in 16 colors, and let you monogram up to six letters. (They memorably use “BUDDY” as their online example.) If your party includes hunting or fishing, note that Orvis will also personalize your fly fishing rods, luggage and more.
For the one who needs a classy long sleeve

To be clear: The brand does not offer monogrammed t-shirts or polo shirts. And yet, the ultra-popular online shirtmaker does offer monogramming on its namesake dress shirts. If your bachelor party includes a nice dinner, or if you want to give the guys something to wear on the day itself, this is a solid option. (Just make sure your grooms do, in fact, tuck it on your wedding day.)
For the one who actually likes uniformity

Here’s a middle option between going DIY and spending on a name brand—services like Corporate Casuals stock up on blank polo shirts, and then offer custom monograms for bulk orders. This is a great option if you have a bigger bachelor party, as you’ll save a little on each shirt, and you want something more like a uniform. This is not an option, however, if you want each shirt to feel personal—meaning your buddy Dave will have a shirt that’s subtly different from your buddy Adam’s.
For the guy who prefers small business

Here’s an idea: Get blank t-shirts or polo shirts from wherever you usually get such things, and take it into an embroidery shop to have it monogrammed. You’ll likely expand your options and save a little money, but lose a bit of the convenience of ordering online. (And, perhaps, the confidence of getting something from a name brand.) A nice move, too, if your go-to shirt brand doesn’t offer monograms.