The Annual Back-to-School Wardrobe List…A Little Late

This post is a little late…but still, the annual back to school list of Old Money wardrobe items is a long-standing tradition here on the blog.

So if you’ve procrastinated and not done your off-to-college or last-year-of-high-school shopping, good for you. This is the one time that putting something off until the last minute will serve you well.

And of course, if you need a go-to guide book for dressing well and not breaking the bank, you can always pick up a copy of Old Money Style (for Guys) and Old Money, New Woman (for Gals). But let’s just focus on the essentials to help you be the original OMG on Campus this fall.

First, the ladies…

I’m going to broadly recommend the following, and then beg Amy, Elle, the 2 Jan’s, Ms. Hemingway, Ms. Bishop, and Good Golly Miss Molly (you know who you are; where have you been?) and all of our other loyal and faithful Old Money Gal Tribe Members to comment and contribute.

I have not visited the states in almost two years, so I have no idea of what’s available, who’s still in business, and what items are a good value right now as far as women’s attire is concerned.

Nevertheless, onward through the fog…

For starters, button-down 100% cotton long sleeve blouses, striped and solid colors, Ralph Lauren or Brooks Bros.

100% cotton short sleeve polo pullovers by Ralph Lauren, Brooks Bros., Lacoste, LandsEd, or LL Bean.

100% cotton or 100% wool crew neck or V-neck sweaters.

Quilted Barbour or Barbour-style hip length jacket for football games.

Khaki pants, Ralph Lauren, Brooks Bros., LandsEnd, LL Bean.

Ragg wool socks by LL Bean.

Subjecting myself again to blog-wide controversy and/or eternal damnation, I’ll nevertheless go out on a limb and suggest a pair of Stan Smith Adidas sneakers (classic green trim, only, please.)

Penny loafers in brown leather.

And the little, but not too little, black dress…and black heels or pumps.

So that was a quick ladies’ check list. Let’s move on to the Old Money Guys.

The 100% cotton button down shirts from Mercer and Sons (blue oxford, best choice), Ralph Lauren, Brooks Bros., LL Bean, or LandsEnd. Start with blue, then white, then blue & white stripes.

The khakis, cotton pants, or corduroy pants from Ralph Lauren,Brooks Bros., LL Bean, or LandsEnd.

The same Barbour style jacket recommended above. The same wool socks recommended above. The same penny loafers recommended above. And even the same Stan Smith’s recommended above. Dressing Old Money Style is so simple, and it’s so convenient to steal and wear your boyfriend’s clothes without anyone even noticing! I know! It’s crazy!

The cotton or wool crew neck or V-neck sweaters, with the Holy Grail being the Shaggy Dog from J Press.

The LL Bean boot for getting to class in cold, wet weather.

And the classic, Old Money ensemble of the blue blazer, dress shirt, and grey slacks for almost any social occasion. Feel free to mix, match, and layer the sweaters, polo shirts, and boots with this for your own, individual look.

So that’s dressing well in a nut shell, to put it poetically.

I’m eagerly awaiting your comments. Thanks again for supporting this annual tradition.

  • BGT





17 thoughts on “The Annual Back-to-School Wardrobe List…A Little Late

  1. Aw, Byron… how can I say ‘no’? Well, I am fairly far from both coasts and fashion here in cow towns (the Rocky Mountains) is several years behind what the W. and E. coasts are doing. Since OMS (Old Money Style) is timeless, and I am a bodaciously curvy woman, I kind of do my own thing. I prefer pencil skirts and blouses/sweaters. Since that sort of style is more vintage, that’s my look. Dresses and skirts. Pieces I can pair. I need to do a closet purge and restock but with things the way they are on the supply chain I am now thinking about how I can make things last a bit longer.
    Unfortunately, I am doing more and more of my shopping online which has its pluses and minuses. One must be very accurate when measuring. Also, because I am curvy, regular preppy labels do not fit.
    I love an LBD. I have down-sized my purses to clutches or clutch-type with small handles.
    My pearls are still my, go-to for everything although I do like the pearl disc necklaces I am seeing here-and-there. I love a new take on classics.
    We do not go out much these days. Our style is more casual around the house. Not only is that because we are going out less but also availability has been affected. Many local shops I used to patron have shuttered and I see better selection on the shopping channels on t.v. than what is available around town.
    I would love to support local businesses but how can I when their stock is so lacking?
    I mostly shop for groceries or items to do simple repairs around the house.
    I did not mean for this to sound so bleak. I started writing and remembering the great shops we USED to have and how much it all has changed in such a short amount of time.

  2. I appreciate the specific stores and pictures. I respectfully might have to disagree with some of the women’s clothing suggestions. Or maybe some just wouldn’t work for me? I love in theory the idea of a button down shirt and polo but I think these styles don’t always work for those more curvy. I noticed you didn’t mention cashmere sweaters? What do you think of those?

  3. I think that’s a good basic list. OMGs tend not to have a huge amount of clothes, but what they have is high quality and versatile enough to be worn in a wide range of circumstances. Unlike Melissa and Kimberly, no one would describe me as curvy. I could probably get half my clothes from the men’s or boy’s department and no one would notice. As far as button downs, Brooks Brothers has gone down slightly in quality (my grandfather must be rolling over in his grave) and L.L Bean currently makes the best polo shirts.

  4. Great list – I would add accessories like a beautiful cashmere scarf in fall colors. I agree that dressing old money style is simple. As you’ve helped us understand, there are many subtle details and nuances to get the “style” in old money style right.

  5. We do our best with the 11-year old Young Master, who recently began 6th Grade (public school). While he is, sadly, now opposed now to dock-siders and desert boots, he does actually like Argyll socks, khaki chinos, Madras, pique knit Polo shirts, ocbd’s, and rugby jerseys. The next step is to resume our efforts to teach wearing a belt and tucking in shirts with tails, which Covid and online schooling at home threw off quite a bit during 2020-2021. A navy blazer, a tie or two, and loafers for dressier occasions are still a few years off. He does, however, cut a very nice figure waiting for the school bus each morning.

    Best Regards,


  6. Each year when I read this much anticipated list, I wonder what student can afford Mercer and Sons shirts. I own over 30 button downs and only one is a Mercer, the rest bought on ebay (Brooks Brothers and RLP) and direct from Lands’ End, which now is off my list due to just recently changing the one traditional shirt they had left, the Hyde Park, from exact sizing to Alpha sizing. If I could afford Mercer, there’d be twenty in my closet, but the two seventh graders need clothes more than dad. But for taste and style, and for actually giving a darn to dress well, my hat is continually off to this list. Bravo.

  7. In the spring someone in the comments mentioned Talbots and they have become a go-to for me. I have acquired a bright shirt dress from them and several button downs (none Oxford cloth but I live in the Carolinas and it is hot here!)

    I am no longer school girl but I do remember going off to college and in the south it would be very important for a young lady to have 1 Lilly Pulitzer style dress, this is what you wear any kind of event that happens in the morning or the early afternoon. It’s the perfect partner for a not-too-little-black-dress, together they have you covered for all social events from showers and church services to soirees and funerals. Add to the tennis shoes, penny loafers, and pumps one pair of sandals (possibly Jack Rodgers style.) Also don’t forget weather enduring footwear for the women! You can’t go wrong with hunter rainboots. Add to those button downs and polo shirts 4 pairs of trousers (or the corresponding A line skirt option) in dark wash denim, khaki, navy, and gray and I believe you could go most anywhere, from a run to pick up groceries to the chancellor’s office (you’ll only be there for good reasons of course). I’d trade that parka for a cardigan and a light blazer (but it really doesn’t get cold where I am,) and possibly a wool pea coat.

    I do love these posts on clothing! ♡

  8. Dearest Byron – Granddaughter Peri just received her first pair of LL Bean boots for comfortable dashes on the Bard campus. While living in Connecticut and raising Peri’s mother, we referred to them as “duck boots”. Not much difference… colors are the same, lining is comfy, warm and dry. xoxo

  9. I would definitely add a navy wool pea coat to this list. It’s one of the most timeliness pieces of clothing you can own. I’ve worn one since I was in college in Boston (Barbour jackets and bean boots are spot on for fall days on Commonwealth Avenue), and it fits right in San Francisco as well where I currently live with my wife. I recommend buying vintage though, since the decommissioned military coats will be the thickest and have the most timeless style (the golden years are from WW2 to the early 1970’s). My current coat is from Fox Knapff from the 1960’s and still looks great 60 years later.

  10. As someone who lives in Maine (home of LLBean), I regret to say we no longer purchase there even though it is our backyard. The quality of clothing has dropped considerably and their lifetime guarantee is gone. Plus, and this was the deal breaker, for the most part they no longer repair most items.

    What do we get for back to school?

    Turtlenecks (ribbed or regular) in cotton, cashmere or silk.
    Polos (with school logo or white. Public schools wear colored polos)
    This isn’t OMG style, but a good quality fleece (think Malden Mills) zip type sweatshirt with a hood, especially if it has the school logo.
    School sweatshirt (regular sweatshirt is kind of tacky looking. School sweatshirt=school Spirit)
    Sweaters of all types, wool, silk, cotton.
    Chinos/corduroy pants and good quality jeans
    Waterproof hiking boots (even private schools allow you to wear them up here and great for snow) We no longer buy duck boots.
    Leather riding boots
    Good quality crosstrainer sneakers or tennis sneakers.
    Leather chukkas
    Good wool blazer
    Long skirts, at least knee and preferably calf length, wool or chino.
    Parka with fleece zip out lining or full length London Fog quality dress raincoat

    For stores, I shop at outlet stores, which are in abundance up here, and the price guides my selection. One month one store may have a fantastic sale on chinos and the next month it is turtlenecks. Some stores I use include Christopher and Banks, Talbots, Champion, Cabela’s, a Maine store called Renys andKohl’s (not OMG store but very good quality turtlenecks at good prices.). I also recently discovered Blarneys, an Irish retailer that carries the most comfortable Aran and merino wool sweaters at very reasonable prices.

    1. @Kellie – I agree with your sentiments concerning L.L. Bean. Also, they went from being an inside label to an outside label and I’m not a fan of promoting brands like the modern L.L. Bean on my clothing if I can avoid it.

      1. Yes, you’re right on the labeling as well. Who wants to be a walking advertisement? I usually will look at off-brands first since they are often less expensive and most are good quality. Now that Cabelas has entered our state, we do a majority of our outdoor apparel shopping there. It’s not an OMG type store, but on their house brands they stand behind their product with their lifetime guarantee and that is my #1 consideration when purchasing clothing. I have a parka that has lasted almost 10 years with a simple zipper replacement.

  11. I agree with both the above writers about button down shirts and khakis not fitting curvier bodies properly. To fix that problem, I predominantly wear linen or cotton a-line and shift style dresses, at or just below the knee, with solid-soled ballet flats, and a thick Aran cardigan sweater and wool leggings in the winter. I spend most of my time at home, even more so with the pandemic, so these are comfortable enough for every day gardening and playing with children as well as pretty enough for going out if I happen to need groceries or visit my grandmother, and I could wear them to a party just as easily. I love having clothes that can go from semi-casual to semi-formal with just a change of accessories, probably the pearls my mother gave me years ago for my sixteenth birthday. I’ll admit that I trade out the ballet flats for wellies when gardening, though, as I prefer for my shoes to have long lives.

  12. Since reading last year’s back-to-school shopping list I’ve been searching for a high-quality OCBD (or at least something similar) for us Old Money Gals. It’s been a challenging quest! Most are synthetic or – heaven forbid – utterly sheer. However, I’ve found a wonderful quality shirt company called Power Of My People. They make all of their 100% linen and cotton shirts in Canada with impeccable construction and ethical manufacturing. Their shirts aren’t seamed or shaped, but are more of a classic straight cut in the style of a men’s OCBD. Great worn a bit oversized tucked into dark Levi’s 501s or with a wool skirt for the cooler months. I highly recommend!

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