Still Stuck on 90s J.Crew? Meet The Modern Prep Essentials.

Here's your starter kit

This letter is sponsored by Sperry.

Prep belongs to all of us. It’s not just for the Connecticut-bred lulled to sleep with fables of early acceptance to Ivy League schools. It’s certainly not contained to a certain proximity to water or enthusiasm for oysters. And despite its origins and current representation in fast fashion (read

Viv Chen

’s essay and then come back to this), prep has evolved since its multiple heydays in the 50s, 80s, 90s, and 2010s, even if its commercial image remains white and WASPy.

dear j.crew, i'll never be your best american girl

Prep is something cared for, steamed and tailored, and returned to season after season. It’s for people who want to dress in classic silhouettes and timeless styles because keeping up with trends is exhausting.

“Prep clothes are sensible: rain clothes keep you dry; winter clothes keep you warm; collars are buttoned down so they don't flap in your face when you're playing polo. Layering is a natural response to varying weather conditions.”

This comes from Lisa Birnbach’s seminal, satirical The Official Preppy Handbook from 1980. These first editions worth a lot of money, if you happen to spot one at a thrift store. She wrote an updated copy in 2011, True Prep: It’s A Whole New World, but I’d stick with the classic. There’s also the cannonic Take Ivy, which was originally published in Japan in 1965. If you want to double click on any of this source material, American Ivy is an incredible podcast season from Avery Trufelman on her show Articles of Interest.

But if you’re less inclined to order a rare book secondhand and a little more interested in dusting off your boat shoes from middle school, you’re in the right place. Here are some of the pillars of modern prep.

Big pants

From 2nd in 2010

This doesn’t mean sloppy. In fact, I’m a big believer that there’s hardly anything as chic as a wide leg pant. Pair this with a rollneck sweater and some loafers—you’d be hard pressed to find a situation where this outfit combo doesn’t make you feel pulled together in the colder months. Come summer, big pants plus worn-in tshirt is another classic move.

Tall people: these are SO long. And at $138, they feel approachable, especially for the quality. I have them in khaki and black.

You think Abercrombie is good now? Try it in the 90s. These vintage pants have that fatigue new pants could only ever imitate.

I’ll keep recommending these because I think they’re that good. And you can always get them for 30% off.

Vintage Polo Ralph Lauren wide leg pants for $50.

For the polished preppies among us, these trousers from Theory are so chic. I love the pleated detail.

Vintage Perry Ellis corduroy, anyone?

Wool blazer

ok boys! This is from Take Ivy

This has to be vintage. It cannot be purchased from a store with a security tag, I beg of you. Thrift stores are overflowing with brilliant wool blazers from uncles who still smoke cigars and vote a lot differently than we do. But secondhand outerwear is the great unifier? We’ll work on that theory a little later. Just be sure your blazer comfortably layers over a button down or a crewneck sweatshirt, depending on how you plan to style.

A stylish tweed option for under $50.

Similar tweed but a good example of the differences in blazer shapes from the 80s to the 90s. This is also under $50.

I guess while we’re doing a history of blazers bit, here’s a piece from the 60s that looks an awful lot like the “shakets” of today.

Ok hear me out: this with the Theory pants above…incredible.

You can tell me if I’m losing it a little, but I think this vintage airline blazer for $25 is quite chic.

Over-the-shoulder sweater

I wear the same sweater over my shoulders on every plane ride! It’s vintage and mended from 10 years ago.

“Always underdress. The goal is not to look as if you made an effort for the particular event. If you can dress for a different party (i.e., wear black tie to a cocktail party, or tennis clothes for lunch), so much the better. You give the impression of being much in demand.” Classic Lisa Birnbach. The hack to getting this look is draping a shoulder around your sweaters. We’ve talked about this before—thin cashmere sweaters are not for this! Try something cotton, which I find has a better drape than wool. A blend in fine. My favorite is a striped sweater.

Subtle neck detail, 100% cotton, and the perfect green/grey to wear over everything. Plus, it’s $25.

A timeless sweater ($250) from La Ligne that feels like the kind of holiday gift I’d love to receive.

This vintage striped sweater from Etsy would be so cool over the shoulders ($45)

I’ve never owned anything from Kule, but I’m a longtime fan. This color combo? Insane. ($350)

Here’s a more affordable option from Alex Mill for $150. There are buttons down the back!

This vintage option has stripes that feel very 90s preppy and is $25!

Another take on blue stripes <3

Boat shoes

In the Buck Mason pants + trench I always swear by

There's an unofficial shoe of the modern prep dresser, and if you've read Long Live for any period of time, you'll hardly be surprised to know it's the Sperry Boat Shoe. I picked up a new pair early this Spring. I started wearing them with jeans and suits and bare legs. The effect was brilliant: a statement shoe with the comfort of a sneaker. And this fall, I can't wait to pair mine with a big wool sweater and a vest. Sometimes I opt for a pair of bright red or blue socks with them, but most of the time, I keep it simple.

If you went for a metallic pair in 7th grade, it might be time to upgrade.

I love this vintage blue leather pair for under $50.

The patina on these! I might buy for Christian…for $40.

A little heel action feels cute with the right sock and a bare leg, if you ask me.

Tartan plaid (but not too much)

We might need a whole letter for Princess Diana outfits…

I mean, do what you want, but I think a touch of plaid, particularly, tartan, is the second-most festive move next to a peppermint hot chocolate. If you’re the type, try tying a tartan ribbon in your hair. Look for tartan lining in vintage jackets. There are ways to embrace the print without asking people to start calling you “Bunny.”

I have it on good authority these are VERY comfortable platforms. Hill House does great tartan, so keep an eye out for their holiday collection. In the meantime, these are on sale for $150!

A very special vintage tartan bag that would look cool with an all white outfit and riding boots.

Ok, imagine this hemmed super short with black tights and boots for the holidays.

This shirt from Frank & Eileen peaking out of a navy sweater…divine.

Vintage GAP tartan skirt in 6 for $30.

Vintage J.Crew men’s vest in medium for all your tartan layering needs.

Pleated skirt

Kelly Rutherford? A real modern prep icon

I can’t be the only kid who grew up romanticising school uniforms. I loved the knee high socks, the crest on the cardigan, but more than anything, those perfect pleated skirts. As an adult, someone confused my October 31st outfit as a Nancy Drew costume…and it was very much the pleated skirt to blame. The key here is finding a length that feels good to you. I’d order something on eBay that’s super long and work with your tailor to bring it to just the right spot where you feel good wearing it with tights to a meeting and with a blousy top and denim blazer to dinner.

This pleated skirt from Land’s End comes in a bunch of sizes and is under $50.

This vintage DKNY skirt is def modern prep, but I can picture it with a huge oxford and loafers.

Please don’t ask me how I found a site where you can make a custom tartan skirt for under $200.

Not pleated, but this $30 vintage Max Mara skirt is very much deserving of a mention.

Simple + chic anges b. skirt for $40.

Busted denim

Bet you weren’t expecting a NASCAR x Long Live moment

This is the most complicated and essential detail to the modern prep look. This, I hate to inform you, has to be vintage 90% of the time. You’ll need denim that looks like it’s lived twice as long as you have. I’m not talking about holes in the knees or under the butt (truly? I’m at a loss for words). I just want a little distressing on the hem and the faded look that only comes from a yearly wash and hang dry. Maybe I’ll do a whole denim letter soon…

Are Wranglers comfortable? No! Do they give you the best bum of your life? Yes. And they’re $50.

Vintage Levi’s for $65 (32x32)

Another $50 jean that comes in long, too.

Vintage Levi’s 505s for $45 (34x30)

Vintage Wranglers Cowboy Cut for $36 in 36x36.

Monogrammed (almost) everything

People are divided on this, and I get it. But I am a Monogram Person, and therefore, will be espousing their glory. A monogrammed gift says, “Hey, I was thinking of you weeks ago and decided you would like this enough to own it with your initials on it.” And instead of sporting a brand or label, you can stake your claim in an item you plan to take care of and treasure for decades to come. Even better? Set an alert for “vintage monogram (insert initials here)” for yourself or someone you love.

Monogrammed flannel PJs that come in tall sizes for under $100! Lands End, baby.

I’m a big believer in monogrammed notebooks.

Take Your Time with Dianna Cohen

put me on to this one.

Or why not Gucci’s monogram? This cutie bag is under $300.

Signet ring

This one, for example, is under $200 on Etsy.

I bought myself a Shinola signet ring when I graduated undergrad and have worn it every day since. There’s something about a pinky ring that feels a little old fashioned and special. Plus, you don’t have to spend a lot of money to get a really high quality one/start to build your jewelry collection.

A Shinola classic for under $200.

Vintage. Bold. Sterling Silver. $70. Also a size 9.5, so kind of big.

Here’s a similar style 1970s malachite signet ring for under $100.

This RING! It’s over $2k so this is not a budget find, but it’s so timeless and kind of a similar shape to my engagement ring. I’ve been really into browsing

At Present

recently.

I love how subtle this signet ring is from Fewer Finer.

Another subtle option that would be very cool stacked. This is $250.

Plus, a cool diamond-y version for under $200.

Wool overcoat

Love means…wearing a wool coat with bare legs apparently?

What would Love Story be without Ali MacGraw’s camel wrap coat? Likely still an incredibly depressing, semi problematic (“love means never having to say you’re sorry”) film, but you get where I’m coming from. Get thee to a thrift store! These are expensive to ship because they’re heavy, so sometimes secondhand sellers will mark them up just because. Stick to 100% wool. And remember, you can always get the lining replaced, usually for $100 at a tailor.

If you want to match, here’s a pretty close twin for you! It’s under $600.

$55 and size 14 from Pendleton!

Here’s the below jacket via eBay (different brand ofc but same idea) for $72.

This coat from ALIGNE is more a silhouette I’d go for. It’s under $500, which can be hard to find if you’re shopping new.

Yes, I know, it’s not wool, but for $100, this gem deserves a moment.

Thank you for reading Long Live. It means so much to me. You can shop my favs here, follow along on Instagram + Tiktok, shop my Notion template, and as always, respond to this dispatch for my direct line x