5 Coastal and Preppy Halloween Costumes for 2026 | Quoddy

Every year, "preppy" ends up on the short list of Halloween's biggest costume categories, right alongside superheroes, celebrities, and monsters.

The appeal is obvious once you think about it: a preppy Halloween costume is one of the only ones you can build almost entirely out of clothes you already own. That way the pieces you do buy don't have to be boxed up on November 1st.

We put together this year's crop of preppy Halloween costumes that lean hard on pop culture and coastal style. Between The White Lotus, The Summer I Turned Pretty, and a couple of older favorites that never really leave rotation, there's no shortage of ways to build a costume around a blazer, a pair of khakis, and a good leather shoe.

Here are five that work whether you're going solo, as a couple or duo, or a group, and the Quoddy pair we'd put with each one.

Why Preppy Halloween Costumes Are Having a Real Moment

Preppy and old-money aesthetics have been building online for a couple of years now, and Halloween is catching up. The old money aesthetic first broke through on TikTok back in 2024, and it hasn't really slowed down since. Glamour reported the trend had "amassed more than 12.5 billion views on trendsetting social media platform TikTok," built around exactly the kind of traditional, heritage-brand pieces (loafers included) this list leans on. That staying power is a big part of why it's carried straight through into summer fashion cycles rather than fading out like a typical microtrend, and Halloween costumes are just the next place it's showing up.

Pop culture is doing a lot of the heavy lifting on top of that. Shows and movies set in wealthy, coastal, or New England worlds keep giving people new, specific characters to dress as, instead of just a vague "rich person" costume.

That specificity is what makes these costumes work. "Preppy costume" on its own is broad enough to mean almost anything. "The White Lotus guest who's about to ruin everyone's vacation" is one that gets the point across, yet is so simple that your friends will probably jump in on the idea too.

5 Coastal and Preppy Halloween Costumes for 2026

These five preppy Halloween costumes span quiet old-money resort energy to full coastal New England, with one deliberately loud exception mixed in.

1. Conrad and Jeremiah from The Summer I Turned Pretty

In the summer of 2025, the third and final season of The Summer I Turned Pretty took the world by storm. You couldn't scroll for a few minutes or go anywhere without hearing "Team Conrad or team Jeremiah?" Now in 2026, the TSITP movie has been filmed, and a holiday release for late this year or 2027 is widely anticipated.

With the movie hitting the big screens soon, the momentum for this series isn't going anywhere by this Halloween. An unbuttoned chambray or a plain henley, tousled hair, khaki shorts, bare ankles, and that specific brooding-boy-at-the-beach-house energy is all it takes. "Conrad vs. Jeremiah" costume splits are already a recurring theme on TikTok and Pinterest. It's also a costume that can double as basically just a well-dressed Tuesday. This is a great pick for brothers or best friends in real life.

Wanna take it a step further? Bring in a couples, group theme, or both with costumes for Belly, Taylor, and Steven, the other main characters of the show.

2. Cher and Dionne from Clueless

Plaid-on-plaid, knee socks, and unshakeable confidence never really left. This one skews easy and photogenic: a plaid skirt, a cropped cardigan or blazer, and a suede mule or loafer.

It's also one of the stronger picks on this list for two people instead of one. Best friends Cher and Dionne are a recognizable and timeless stylish pick this Halloween: with two different plaid colorways, and an optional beret or top hat, this is an easy yes for best friends who want to coordinate without matching outfit for outfit.

3. Jordan Belfort from The Wolf of Wall Street

Every other costume on this list is quiet money, but this is one is loud. Played by Leonardo DiCaprio, Belfort's off-the-clock look is a white polo, khaki pants, sunglasses, an oversized watch, and loafers or moccasins to finish it off. It's been a reliably recognizable costume for over a decade, no new movie or season needed to keep it relevant, and it's a generally easy costume to throw together last minute if in need of a solo costume.

However, if you need to plan a costume with someone else, look to the supporting characters. This solo costume can easily be made a duo by pairing with Naomi (Margot Robbie's character) or Donnie (Jonah Hill's character) throughout the Wolf of Wall St.

If you'd rather go all out than throw together the easy version, there's the dressier route: Belfort's dark pinstripe suit from the Steward Bank IPO scene, slicked-back hair, and a red tie, the exact image most people picture when they hear "Wolf of Wall Street" in the first place. It's a bigger lift than the polo and khakis, but it reads as a much sharper, more specific reference, and it's the one version of this costume where people won't need the watch or the loafers to know exactly who you are. The brown blucher and the brown Rover Penny below work under either version of the look.

4. A Guest of The White Lotus

This show isn't slowing down either. HBO has confirmed a fourth season, moving the action to the French Riviera with guests checking in across two resorts in Saint-Tropez and Cannes during the film festival, with a cast list that's kept growing by the week and a premiere expected sometime in 2027.

Nobody does "rich person on vacation" quite like this show. The costume is mostly attitude: a linen shirt with one too many buttons undone, sunglasses pushed up on your head, and the specific tension of someone who's about to have a very bad time at a very nice resort. It's one of the most-referenced pop-culture costume categories heading into this Halloween, and it photographs well because the whole look is built around a real setting, not a movie soundstage.

Here are a couple of pairings for him and one for her:

5. Coastal Grandmother

The one non-movie, non-show pick on this list, and arguably the most wearable costume here with any group number. Linen trousers, an oversized button-down, a wide-brim hat, and the general energy of having just come from a really good lunch. Unlike the others, this aesthetic isn't tied to a single title, so it won't feel dated once the next season of anything comes out.

Which One Matches Your Effort Level?

Some of these preppy Halloween costumes come together in an afternoon; others take a little more planning. Here's how we'd rank them.

Making It Work for One Night

You don't need a full break-in period to wear a new pair of leather shoes for a single night out. Wear them with a real sock rather than sockless the first time, and give them a short walk around the house before you leave so you know exactly how they feel before you're standing in them for hours. If you're planning to keep wearing the shoe well past October, which is really the whole point of this list, our guide on how to break in leather boat shoes covers how to do that properly over the following weeks.

If you're deciding between a boat shoe and a loafer for one of these looks, our comparison of boat shoes vs. loafers breaks down which one fits which occasion. And once the costumes come off and the weather turns, our guides to chukka boots and slippers cover the rest of the season.

Shop the Nine Pairs

All nine pairs from these preppy Halloween costumes, in one place, scroll through to browse.

Repurposing for New Occasions

A boat shoe or penny loafer you bought for one night doesn't have a natural end date the way a costume does, it just moves on to the next thing on your calendar.

The Runabout works for cookouts, tailgates, or travel days, and the Calais boat shoe fits a boat trip, a beach weekend, or a casual Friday at the office. The navy boat shoe from the White Lotus pairing covers anything outdoorsy or waterside, while the burgundy tassel slip-on works for a dressier night out. The Clueless Moxie Mule and the Coastal Grandmother sand suede loafer both suit office, dinner, or holiday-party wear. And the brown blucher from the Belfort look pairs just as easily with jeans or chinos once the polo and khakis are gone, making it a comfortable everyday option well past October. The Rover Pennys in Brown and Capetown Trail work the same way, with a lug sole that suits cooler, wetter weather, and the Capetown pair slots into the same dressier-night-out rotation as the burgundy tassel slip-on.

Getting that kind of mileage out of a leather shoe does mean giving it a little upkeep, especially if a boat shoe ends up somewhere actually near water. Rinse off salt water or sand as soon as you can rather than letting it dry into the leather, and let wet shoes air dry away from direct heat or sun, which can crack and stiffen leather over time. A leather conditioner every few months keeps the material supple and helps it resist water rather than absorb it, and rotating between two pairs, rather than wearing the same one every day, gives the leather and the footbed time to fully dry out and recover its shape between wears.

Shipping Times: Will It Arrive by Halloween?

Not every Quoddy style ships on the same timeline, and that matters a lot more in late October than it does the rest of the year. Before you order, it's worth knowing which category your pick falls into.

In-stock pairs are processed within one business day and ship within 3 to 4 days from there, plus standard transit time. The Runabout Shoe and Calais Boat Shoe (TSITP), the Moxie Mule in Mushroom Suede (Clueless), the Brown Blucher Shoe and Brown Rover Penny (Belfort), the Navy Quoddy Head Boat Shoe, Capetown Trail Rover Penny, and Burgundy Windham Tassel Slip On (all White Lotus), and the Sand Suede Penny Loafer (Coastal Grandmother) are all true in-stock pairs, so every pick on this list is a safe bet even ordering close to Halloween itself.

If you go looking through the rest of Quoddy's styles beyond this list, keep in mind that Made to Order pairs run on a longer build time, generally around 4 to 6 weeks depending on the style, with a rush option available depending on the time of year and material availability. If you're eyeing one of those for Halloween this late in the season, it's worth reaching out to Quoddy's customer care directly to confirm it can realistically arrive in time.

When in doubt, check the product page itself. Quoddy labels in-stock styles clearly, and a quick message to customer care can confirm exactly where an order will land before you commit to it.

Final Take: Building a Preppy Halloween Costume That Lasts

The best preppy Halloween costumes borrow a specific, recognizable character rather than a generic idea of "prep," and they hold up because the elements are things you'd wear on a normal Saturday. Pick the reference that fits you or your group, build around clothes you already own, and finish it with a real leather boat shoe or loafer.

Frequently Asked Questions About Preppy Halloween Costumes

What is a preppy Halloween costume?

A costume built around classic prep, old-money, or coastal New England style: blazers, khakis, boat shoes, loafers, and clean, neutral colors, often tied to a specific pop-culture character rather than a generic "prep school" look.

What are the most popular preppy costumes for 2026?

The White Lotus, The Summer I Turned Pretty, and Clueless are all showing up in 2026 costume trend coverage, alongside the evergreen Coastal Grandmother aesthetic and the reliably popular Jordan Belfort look from The Wolf of Wall Street.

Can I wear a boat shoe or loafer without breaking it in first?

Yes, for a single night. Wear a real sock the first time out and walk around the house briefly beforehand. A full break-in matters more if you plan to keep wearing the shoe regularly afterward.

Do I need to buy a whole costume, or can I build one from my closet?

Most of these looks are built from wearable pieces: a linen shirt, khakis, a blazer, a plaid skirt. The shoes are usually the one piece worth buying new, since they're also the piece you'll keep wearing.

What's the difference between a boat shoe and a penny loafer for these looks?

A boat shoe reads more casual and coastal, better for beach or resort-set characters like The White Lotus or Summer I Turned Pretty. A penny loafer or suede mule reads more polished and collegiate, better for Clueless or Coastal Grandmother.

Is the preppy costume trend just for women?

No. Jordan Belfort or the brothers look from The Summer I Turned Pretty is menswear-driven, and boat shoes, bluchers, and loafers all work across these looks regardless of who's wearing them.