Making the Grade

Back to school fall fashions for adult learners.

I bought a pair of Bally loafers for fall on Friday that brought on a wave of nostalgia. They are very similar to the blucher moccasins I wore to school and made me reminisce about all the classic preppy clothes of my adolescence and collegiate years. My style is still essentially the same but just a bit more sophisticated now that I live in NYC instead of Boston.

I’m a visual person and always think in images. I can’t start any post without finding photos to illustrate what I’m trying to convey with words. The first place I went to for my back to school theme were movies set at boarding schools and college campuses.

One of the silliest films that has the best preppy fashions is Making the Grade from 1984 with Judd Nelson. It’s not streaming anywhere but luckily someone uploaded the full film to YouTube. The plot is one of the usual tropes of an outsider trying to fit in where he essentially doesn’t belong but the clothes make it worth watching.

The Sure Thing from 1985 is also a bit silly but Daphne Zuniga wears the best fall/winter New England college classic fashions as she spars with John Cusack on their comedy of errors road trip across the country. Her sweaters alone deserve their own future post. It’s also not streaming but another person was kind enough to upload it to YouTube.

The 80s were a treasure trove of prep school films and Class from 1984 is a not so great film with great preppy fashions. It’s free to watch on Amazon Prime. I don’t want to give too much away if you haven’t seen this one but Rob Lowe and Andrew McCarthy play roommates who have a falling out over an older woman. It also stars John Cusack who, fun fact, I matched with on Raya years ago but who promptly unmatched with me after I sent a very innocuous message.

You could also watch some of the more high brow preppy films like Dead Poets Society with duffle coats that remind me of all the ones I wore in college. There is also School Ties but I don’t think it’s as good as the rest. Love Story is another classic rich boy poor girl story with iconic preppy fashions.

Before someone says that this fall fashion post is too early and summer isn’t over yet, blah, blah, blah, hate the game not the player. By the time it’s actually cold enough to wear fall fashions, all the good stuff will be gone. One of my friends in Spain sent me a link to a sweater from a certain retailer that he knows I will want for fall that hasn’t been released in the US yet. They completely sold out within days.

On Friday, I also posted an update to my Quilted Jackets, Field Coats, and Barn Jackets post on my OG Habitually Chic blog. I found a great vintage 90s Hermès Paddock Jacket from Margiela years that I can’t wait to wear this autumn. That’s the exact one above. The closest version available now is the Toteme oversized quilted jacket which is on sale now. It runs big so you may be able to size down one to two sizes.

I can’t resist a grey cashmere sweater and Cos makes some of the best quality ones so I just ordered their new grey cashmere sweater. Their sweaters usually run large so you can probably size down at least one size and sometimes two but check the dimensions before ordering.

If you want your white tee shirt to peek out above your sweater, choose a higher neck one like this classic fit crewneck t-shirt.

I don’t wear jeans that much except in the fall so I just ordered these curvy cropped kick-out jeans in the dark wash. I wish the lighter color looked exactly like they do on the model because I would get those too if they did. The already raw hem means you can cut them to your perfect length. I use Fray Check to keep them from fraying too much and looking messy.

I bought the Bally leather loafers from Net-a-Porter but the burgundy and brown are already almost all sold out since I posted them in my Instagram Stories yesterday. They do have black in a full size run though. You can find more brown leather here in stock and brown suede here. I found they run true to size.

You can find a less expensive but very similar brown leather loafer here.

I’m still waiting for the Bally bag I saw on the fall 2024 runway to become available so in the meantimes, I’d suggest this burgundy leather shoulder bag or this larger burgundy shoulder bag.

I’ll be wearing my Linda Farrow x Cos Aviators this fall which are sadly sold out so I’d suggest these brown aviator sunglasses instead. Or these aviator sunglasses.

I think we should all reread The Secret History together this autumn and create a chic book club.

Sofia Richie wore the Loro Piana Sydney Leather-Trim Cashmere Knit Poncho to Europe last year and I fell in love with the fabric but not the price tag. To be honest, I would never wear a cape or poncho so when I saw this somewhat similar Altuzarra Medrano Faux Leather Piping Jacket, I decided to take a chance. I had a gift card from Bergdorf Goodman that I received for my birthday that I was saving for something special like this jacket. It’s also already selling out but you can find more in stock here, here, here, and here.

The grey cashmere sweater above also comes in brown cashmere. The warm colors of the outfit call for an off white Supima relaxed t-shirt.

The High Rise ’90s Straight Jeans are a great price for a great style.

I love a tan suede loafer for fall. These are a great less expensive option.

I wish I had a tan suede tote when I was in school. This tan leather bag is a great less expensive option.

Top off your outfit with these aviator tortoiseshell and gold-tone sunglasses.

The Catcher in the Rye is another classic novel to reread this fall.

If you need an outfit for weekends in the city or country, this one is for you.

You could go with the classic Barbour Waxed Cotton Coat or the updated Toteme Country Jacket with suede elbow-patches.

The Original Cashmere Sweater comes in olive and 27 other colors for the amazing price of $98. I own a few of these and the quality is great. I also love this heavier textured olive green Recycled Cashmere Sweater.

You can try this white Organic Cotton Slim Crew Tee but my all time favorite white tee shirt is the $6 white tee shirt from Tar-jay.

If you are nostalgic for the 90s than these 90s pinch waist long high-rise straight-leg organic jeans are for you.

This is a less expensive but very similar brown leather loafer to the Bally version.

My first designer bag was a navy canvas Gucci bag which makes me want to get his Gucci small canvas tote bag for fall.

I’d top off this outfit with gold aviator sunglasses.

A Separate Peace tells the story of friendship between two boys at an exclusive New Hampshire prep school as it parallels the inescapable and escalating atmosphere of World War II.

N.B. The best waterproof spray to protect your shoes, boots, and bags this fall, and especially important for suede, is this Crep Rain and Stain Protector. It just started pouring in NYC which also made me think about my favorite umbrella. It’s $26.99 but amazing quality with an open and close button to make getting in and out of cars without getting wet a breeze. I prefer the one with the strap so you can carry it easier and hang it on a doorknob but there is another style without one. It comes in seven colors and I own a bunch so I can match them to my outfit. Yes, I am that crazy!

“If you’re not sweating while buying a coat, you’re doing it wrong.” - Habitually Chic

You can scoff at posting jackets and cashmere at the beginning of August but you snooze you lose when it comes to buying fall fashions.

XOXO,

HC