my preppy style uniform | updated for fall 2020
can you believe it’s october first?! break out the halloween decor, because it’s time to get ready for the holidays! today is also thursday, and you know that means a romp through the archives. today’s retrospective is all about the main components of a preppy wardrobe. i have collected three posts from recent years that all revolve around my go-to preppy aesthetic – it’s my preppy style uniform. these preppy basics are always in fashion, and so my favorite brands always have new versions each season. while the exact items from the past posts may no longer be available, i have collected current offerings just perfect for this fall.
dot your “t”s and cross your “i”s | polka dotted preppy fun
today’s outfit is great for mild-to-cool weather travel. i have a classic white button-up and a polka dot sweater that can each be worn alone, to create two other outfits on my trip – so, three outfit options with these two items. the blazer can go multiple ways as well: it can go over a dress for an evening out, it can even go as a second layer under a puffer or overcoat if it’s really cold.
spotlight on the blazer
blazers are probably at the top of the preppy style list. especially when it’s wool, twill or tweed with a plaid, houndstooth or herringbone pattern. but it doesn’t end there. the shape of a blazer, in general, fits with the preppy aesthetic. remember, we’re talking about a style that evolved from the prep school uniforms of the northeastern US. so, blazers and loafers were/are central to the look.
stylish self-expression as we age
who are you? probably one of the most basic questions; and probably one of the most debated ones throughout history. i’m not a philosopher, so i don’t and won’t have any deep answers here. but today i’m thinking about the idea of self-expression through style. as a reader recently pointed out, when a life event like a death happens, you’re gonna reflect on who you are in some form or another—like it or not. and this week since i’ve talked about career and trailblazing women through the lens of fashion, i thought i’d turn it inward: how do we express ourselves through fashion, especially as we age?
spotlight on oxfords and loafers
oxfords and loafers are foundational to preppy style. i particularly like a penny loafer. J.Crew, Madewell and Everlane all have loafer and oxford styles that i love.
monday blues
imagine my delight when i came across this faux wrap skirt that’s a little bit preppy and a whole lot of cute. and the asymmetrical hem? it’s fresh and modern and gives this skirt the zing it needs. there are so many ways to style this little number but the temps are mild enough today to get by with a shirt and sweater. guess what? i may not have blue pointy toe flats like i used to but i do own these adorable kate spade velvet ballet flats that’ll give me that preppy vibe i’m so fond of. but i did want to draw attention to this adorable shirt by madewell. it’s called an ‘ex-boyfriend’ shirt so it’s oversized. take a peek at the back panel. the stripes are different than the front. the yoke is horizontal and the back has a thinner strip than the front. genius!
spotlight on a-line, pencil and pleated skirts
the clean lines of an a-line, pleated or pencil skirt is another cornerstone of preppy style. whether the skirt is corduroy, wool, denim, cotton or leather; it’s the shape of the a-line, or pencil, and the sharpness of the pleats that make these classic preppy staples. while this blue corduroy a-line skirt is a few years old, Talbots has a lovely burgundy one this season.
today’s post is but a few examples of my preppy style uniform. if you scroll through the archives you will see just how much mileage i get out of this classic style. its elements are always in style, no matter the season, so it makes putting together an outfit a snap. what is your style uniform? what’s your favorite preppy style item? let me know in the comments below, have a great thursday!
Talbots outlet is having a massive sale! Jackets and shoes are $14.99. Jeans are $9.99. Many styles are 60% off. I purchased a navy double breasted blazer, a tweed jacket and suede booties for $14.99 each! All are on trend. It’s definitely worth a visit.
who doesn’t love a good sale?!
You didn’t give us the places you shopped for today’s post nor did you show us the back of your stripped shirt you talk about.
if you click on the read more button you will be taken to the blog post that talks about the clothing items.
I have always loved polka dots and this combo is especially fun with the blazer. I think this would also work for spring if you swapped the blazer in a different color like pink, coral, or green.
good idea, gloria! love it when we can transition items from season to season.
I’m really enjoying your blog – thank you 🙂
I’d love some details on your bags as well, please – especially the off-white one in the first image
ignore that post, please – I’ve just found the info
good! you figured out to click on the read more button. cheers!
Looking good! I like to call my style preppy with a twist. Everything in my closet works together. It wasn’t really any definite plan, but it just worked out that way. Every season I refresh my wardrobe at Talbots with a few pieces. I just added several new items for fall, as well as a couple of pairs of shoes. Since we are all spending the majority of our time social distancing these days, I have decided to finish up the fall/winter by “shopping in my closet”. It’s kind of fun to go through your closet to remind yourself what you have. The preppy style is timeless.
classic style with a preppy twist will always be my go-to look. it’s so simple and as you suggested, lyn, timeless.
Beth you are simply classy. Keep it going.
How would you wear a plaid full shirt? what would you put with it? Would you pair it with tennis shoes and jeans or straight leggings and short bootees?
I am in Chicago and we are approaching fall – thanks!
Evelyn