Preppy Guy Gift Ideas

Preppy Guy Gift Ideas


Bass Men's Douglas Rain Boot Dockers Men’s Vargas Leather Handsewn Boat Shoe Quality Umbrella from London Vineyard Vines Shep Shirts WOODIES Walnut Wood Sunglasses Leather Architect Men's Real Leather Braided Belt Timex Unisex Weekender Watch Gentlemen's Manual GiftTree Leather Bound Golf Log Journal KomalC Genuine Leather Duffel Weekend Bag KOMALC Genuine Buffalo Leather Unisex Toiletry Bag Retreez Classic Anchor Pattern Woven Men's Tie RockDove Men’s Flannel Lined Moccasin Slipper with Memory Foam Premium Personalized Coasters Set with Metal Rim Personalized 5 pc Whiskey Decanter Set Handmade Blue and White Fabric Wrap Bracelet For Men Set WIth Silver Plated Anchor World Poker Tour 500 Chip Poker Chip Set with Dice, KEM Playing Cards and 8 Drink Coasters ASNEY Upgraded Magnetic Chess Set, 12” x 12” Folding Wooden Chess Set with Magnetic Pieces DecoreBay Executive Unisex Black Wood Valet sunglasses, watch, phone, and box storage Itslife Men's Vintage Look Genuine Leather Checkbook The Official Preppy Handbook by Lisa Birnbach Gentlemen's Manual

I know guys are usually tough to shop for, but this preppy guy gift ideas list will make your shopping a lot easier and faster.

The key to any preppy guy gift ideas list is to make sure, above all else, that the items will last.

Quality made item save money in the long run are are the corner stone of a preppy gentlemen’s lifestyle.

Preppy guys are famous for buying classic items and taking care of them so they last forever.  They are also very functional and make sure every item has multiple purposes. They are almost minimalist in nature.

Great news, most of the stuff on this list are high on the quality but not overly expensive, and im my opinion, worth every penny.

Lets get started wit my preppy guide gift ideas list.

Preppy Guy Gift Ideas

1. Boat Shoes

In the preppy world, the boat shoes are king.  Preppy love quality so the brands to stick with are Sperry, Docker, and Rockport are all great options here. 

Brown leather is the safe type to get but I also really like canvas in different colors to mix things up a little.  Have fun and remember, never wear socks with boat shoes.

2. Duck Boots

The boat shoe is the Summer staple like the duck boot is for the Winter. Every Winter my duck boots come out during every snowy and rainy day but they are perfectly fine to wear everyday if you want. 

A great pair of ducks are the Winter staple for most preppy guys and even make appearances in the Fall and Spring too. The color choices makes this a very interesting shopping experience. I recommend taking the prepster with you when getting the ducks to make sure you line up with the large number of color choices.

In this case, Sperry, LL Bean, and GH Bass are great options but there are plenty more to pick from.

3. Umbrella

Every preppy guy gift ideas list needs a quality umbrella on it.  This is the calling sign of a proper gentleman that I recommend he get several (and I’m a minimalist).  I keep one in every car, a larger one in the trunk, one by the front door, and one by the back door.

These 3 are incredible choices and I have them all. The biggest difference is in the handle. The Collar and Cuffs is my favorite handle and they also make a travel version that I own and use often.

4. Anything Vineyard Vines

I buy everything Vineyard vines (and Polo and J. Crew) all the time but nothing beats the Vineyard Vines Shep shirt.  I bought 5 in different colors and wear them all the time.

Other options are the core Vineyard Vines polo shirt and their great plaid button down shirts.

Last but never least is the Vineyard Vines tie.  This is what started it all and clearly makes the statement “Everyday should be this good”.  Since this is also the motto of the average preppy guy, Vineyard vines and preppy go together like sailing and sunshine.

5. Sunglasses

Given that preppy guys are in the sun all the time, great sunglasses are a requirement.  The classic types are always the best and never go out of style. 

This includes the Wayfarer, Aviator, and Clubmaster.

I prefer the wood look and have fallen in love with my Woodies Wayfarer but I try and balance my sunglass wearing between my Aviators and Clubmasters too.

6. Braided Belts

The one way to spot a preppy from other people is in the belt he chooses to wear.  Most guys tend to play it save with leather brown or black belts, but not the preppy.

Most preppy tend to wear colorful belts with fun nautical or sport stuff on them, and they can never have too many.  I tend to prefer a different type (but the nautical themed ones are always a great options).

I prefer braided belts that come in both leather and stretch cotton.  The cotton ones come in many different colors and patterns and are a great option to mix things up.  Most of the major brands started mixing leather with other material (like plastic) that breaks apart in under a year. Most belts with latch holes are made this way so I just avoid that design. Buy quality and it will last.

I bought the 3 pack of woven belts and wear them often. These are not quality belts made in China and have very weak buckles. I have been very careful and so far they have lasted well over a year and not a single problem. Even these are not made like the others, the great price qualified them for this list. I still prefer quality belts over the cheaper pack but wanted to give a wide choice of options for this preppy guy gift idea list.

7. Preppy Watch

I have a whole separate article just talking about preppy watches and give a lot of advice in that post.  Check it out here.

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For a great preppy watch, look for a high quality simple version that you can mix and math with different bands.  If you get a few watches, make sure they all have the same band size so you can switch bands between everything multiplying your styling options.

I prefer a great Swiss or Japanese watch whenever possible and go through great lengths to avoid anything made in China.

8. Golf (Sport) Stuff

Most preppy guys are into some sport so getting something sport related is a no brainer.  Always remember, quality is the most important thing when buying anything for a preppy.

Little things like a monogrammed ball marker, green repair tool, score card holder, or even a shoe bag are great options for the golfer.  For a sailor, sun glass strap or a pair of binoculars will be an excellent choice.

8. Overnight Leather Bag

These could get pretty pricey as good bags cost several hundred at least.  I personally think its is worth every penny but make sure an investment like this will fit his personality.  For example, I love brown leather and will never mix carrying both a brown and black bag with me. Always best to make sure all your bags are at least the same color and style.

Overnight bags serve multiple purposes and can work well at the golf club, carrying gear to the boat, business travel, and carry your workout gear to the gym (stretching here).  You get the point, good bags are very versatile which is why it will be treasured by the preppy guy.

9. Bottle of Scotch

Every guy needs to try a quality scotch and it will take a few bottles to get use to it.  Why not get your preppy guy started with a great starter bottle and see how it goes.  Remember to drink responsibly.

I have a separate post about 10+ bottles of scotch for under $50 that are highly recommended.  I personally tried most of these and can say all are great buys and taste great.

You can also get those small single glass bottles to try different types but most often, you will not find the really good stuff there. Best to go with a great (but still affordable) bottle and really give scotch a chance.


Monkey Shoulder 12 year old


Glenmorangie Original 10 Year Old


Kirkland 12 or 18 year Scotch

10. Grooming Kit and Bag

I have a great Fossil grooming bag and I love the quality of the leather.  Its nice and think and screams class.  It is breaking in nicely and will last several lifetimes if I maintain it (of course I will).

Size is important since you need to find the right balance between big enough and something that will easily fit into a overnight bag.

I recently down sized my bag and can still fit everything (including the electric razor) in my small bag and it fits great in my weekender.

11. Nautical Tie

Preppy’s need to work and why not express your preppy-ness while in the office.  A great nautical tie is a perfect fit between professional and fun loving.

Finding a quality tie is important but since ties are very trendy, it is OK to get something a little cheaper since it will quickly go out of style.  I prefer Vineyard Vines but given their price tag, I often try to get a quality tie for around $20. 

Here is a great list to get you started.  Have fun.

12. Slippers

Slippers are a funny thing, some guys love them, and others will never wear them.  Know your preppy guy before you consider getting a good pair of slippers.

For my whole life, I never wore slippers but last year, someone bought me a great (and extremely comfortable) pair of slippers and I’ve been a slipper fan every since.

That was the key for me.  They needed to be very comfortable, something I could get away while wearing inside the house, and also wear while walking to the mailbox.

I love the plaid ones or something that also look like boat shoes.

13. Engraved Coasters

This is something that goes great with that bottle of scotch or decanter.  Why not personalize a great set of leather or metal coasters for your preppy guy?

I also like mixing in a little nautical theme items (or golf) to make it a little more personal.

There are personally endless material and design options here so have fun picking something that would go with his personality.

14. Decanter

No preppy guy gift idea list would be complete without a quality, crystal decanter.

Most preppy guys are already into scotch and have a few bottles at home already. Why not get him a nice decanter to put it in.  Remember to avoid any crystal with lead in it’s not good to drink lead. 

I personally like the ones that can be engraved but also like the elaborate designed ones a lot too.  Please avoid the ones made in China since I don’t trust the quality.  I have a nice one made in Italy and I love it.

15. Nautical Bracelet

Be careful here.  Some preppy guys could either love or hate bracelets.  I wore them when I was younger, hated them when I got older, and today have mixed feelings.

In order for a bracelet to mean something, it needs to be a style that he loves. Maybe he’s a sailor or loves to fish. Maybe he’s a golfer or into surfing. The bracelet needs to be an extension of him and his activities.

Less is more here as most preppy guys like understated items. Leather or simple rope items are best.

16. Poker Set

All guys love playing cards and a quality card set is a great way to spend an evening.  I personally don’t think you need the official tabled with the green felt. I had one for almost 20 years and I maybe used it twice.  It looks pretty but a pain to keep clean and offers little to the game.

Instead, put that money into a few quality sets of cards and chips.  There is a great difference between the chips and I recommend the sets that usually cost over $40.  I like a nice wooden case that can look great in your study, game room, or family room and can be taken out anytime you want to play.

17. Chess Set

Every preppy guy wants a high quality chess set to spend those quite nights in strategic thoughts with great friends and family.

I love all types from wood, stone, metal, and everything in between (except plastic).  Personally, I have a nice travel magnetic set that fits nicely on the bookshelves in my study. 

I am looking for a second (larger and totally geeky) set that I can display in my game room but these can get quite expensive. Plus I am still looking for the one that fits my personality the best. Lots to choose from and very fun to shop for.

18. Valet

A proper gentleman back in the day always had a valet but in modern times, that just is not practicable.

These great valets are extremely useful and come in many different designs. They also come in clothing valet that will hold your suit and accessories to better prepare for the following day.

I have 2 of these. One to just hold my watch collection, and another one to hold everything else. Both are extremely useful and highly recommended.

19. Leather Accessories

I love leather as it will last a lifetime if cared for properly.  It is also easy to monogram and personalize it to make it special.

Many cool guy things can come in high grain leather including gloves, book covers, wallets, passport and notebook covers, and many other things.

Remember the type of leather your preppy guy prefers and try to buy similar colors, stitching, and type.

20. Books

Every preppy guy should love the classics and having a good collection of leather books in your study not only looks great but it can provide you years of reading entertainment.

I love collecting the Franklin Mint or Easton Press editions and you can find these on eBay for a pretty good price ($20-100+).  Condition is everything and make sure you are buying the best quality you can afford.  A good book collection will be passed down from generation to generation.

No true preppy guy gift ideas list would be complete without the original 1980 copy of “The Preppy Handbook” by Lisa Birnbach. This book has been out of print for many years buy copies can still be bought used on eBay and Amazon.

This is a must for any preppy book collection.


There are countless other preppy guy gift ideas but this list of 20 will easily get you started own the right road. Remember, preppy guys love quality stuff that will last a lifetime so buy with this in mind.

In the mean time, please leave me a comment below and let me know if this was helpful.  If not, what do you think I left off and I will be happy to add it to help future readers.

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