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Preppy gets a strange reputation on the weekend. Most of what’s out there looks like a school uniform or a country club dress code, and neither is what you want to wear to get coffee.
The casual version is easier and a lot more comfortable: one collegiate piece, good denim or chinos, and flat shoes. Nearly all of it exists secondhand in real cotton and wool, for less than the new polyester version.
Below are nine outfits with the tell for each hero piece, including a zipper check that shows you a shrunken sweater before you ever try it on. For the dressier side of this look, I covered how to dress old money on a thrift store budget separately.
Navy rugby shirt, light wash jeans, white sneakers
Start with the easiest one. A navy and cream striped rugby shirt, light wash straight leg jeans, and white canvas sneakers. Push the sleeves up and leave the collar open.
It works because the rugby shirt does all the talking and everything else stays plain. Size up one so it hangs loose over the waistband.
The tell: a real rugby shirt was built to be grabbed, and it shows in three places.
- The collar. White cotton twill, stiff and woven, sewn onto a knit body.
- The buttons. Rubber, so they flex when you press one. Hard plastic usually means a lighter fashion version.
- The weight. Heavy cotton jersey that hangs straight and doesn’t cling.
$18 to $40 gets a good one.
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Forest green quarter zip, white tee, stone chinos
The tell: look at the zipper before anything else. On a wool quarter zip it should lie flat against the chest. A zipper that ripples like a tiny roller coaster means the knit shrank around it in a hot wash, and the body will be shorter and tighter than the tag says.
Once it passes, the outfit is simple. A forest green lambswool quarter zip over a white cotton tee, stone chinos, and brown penny loafers. Zip it halfway so the tee shows at the neck.
Lambswool or merino on the tag beats acrylic for warmth and for how it ages. Acrylic is fine for a few dollars and tends to pill by midseason. Good wool ones run $15 to $35.
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Light blue V-neck, white tee, cream jeans
A light blue cotton V-neck sweater over a white tee, cream straight leg jeans, and tan suede loafers. This is the one I’d wear most.
Pale blue and cream do the work here, soft and a little sunny on a grey day. Tuck only the front hem into the waistband.
The tell: the fiber line on the tag. Pima or Supima means long staple cotton, which pills less and holds its color wash after wash. Then pull the ribbing at the hem and cuffs. Ribbing that springs back means the sweater still has years in it.
$15 to $30 covers most. Cotton is the right call for early fall, since it layers without overheating.
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From the Avant Heir Closet
One of One
Red plaid flannel, white tank, dark jeans
This one costs almost nothing. A good cotton flannel shirt runs $12 to $25.
Wear a red and navy plaid cotton flannel shirt open over a white ribbed tank, with dark indigo straight leg jeans and brown leather boat shoes. Roll the cuffs twice. The open shirt acts as a light jacket, and the dark denim keeps the red calm.
The tell: flip the cuff. Woven plaid is dyed in the yarn, so the pattern is just as strong on the inside. Printed plaid looks pale and blurry on the reverse, and it fades faster. If the inside matches the outside, it’s the good one.
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Grey sweatshirt, pink oxford, olive corduroys
The common mistake with a sweatshirt is wearing it alone and hoping it looks preppy. The collar underneath is what gets it there.
A heather grey crewneck sweatshirt over a pink oxford cloth shirt, olive corduroy trousers, and grey suede sneakers. Pull the collar out. Let the shirt hem show an inch below the sweatshirt.
The tell: the cotton percentage on the tag.
- 80% cotton or more. Thick, holds its shape at the neck, softens with age.
- 50/50 blends. Thinner and softer, fine for layering, more likely to pill.
- The neckband. It should sit flat. A wavy, stretched neckband won’t sit neatly over a collar.
$12 to $30. Throw a blazer on top and you’re in casual old money black blazer outfits territory.
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Fair Isle yoke sweater, mid blue jeans, ballet flats
The prettiest sweater on this list, and the one most often imitated with a print.
A cream wool sweater with a navy and red Fair Isle yoke, mid blue straight leg jeans, and burgundy leather ballet flats. The yoke frames your face the way a necklace would, so skip the jewelry. Keep everything below the sweater plain.
The tell: turn it inside out. Real colorwork leaves floats, short strands of yarn carried across the back of the pattern. A perfectly smooth inside usually means the pattern was printed or stitched on top.
The tag should say wool, often Shetland or lambswool. $25 to $60, and worth it.
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Black Watch kilt, camel crewneck, black loafers
Can a kilt be casual? With a plain sweater and flat shoes, yes.
A navy and green Black Watch tartan wool kilt, a camel lambswool crewneck, black tights, and black penny loafers. Tuck the front of the sweater so the waistband and buckles show.
The tell: three things separate a real kilt from a pleated skirt in a plaid print.
- The closure. It wraps across the front and fastens with leather buckle straps at the hip.
- The pleats. Stitched down flat from waist to hip, then released. There are a lot of them, which means a lot of fabric.
- The tag. Pure new wool, often made in Scotland.
Knee length is the easiest length to wear casually. $20 to $45.
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Olive quilted vest, striped tee, black jeans
For the in-between days when a jacket is too much and a sweater isn’t enough.
An olive diamond quilted vest with a corduroy collar over a navy and white striped long sleeve cotton tee, black straight leg jeans, and tan suede driving moccasins. Leave the vest unsnapped so the stripes show.
The tell: run a hand over the quilting. Every diamond should be stitched closed, because broken quilting thread lets the fill slide toward the hem and leaves flat, cold patches. Then press each snap. It should close with a firm click.
$20 to $45 is the usual range.
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Navy knit polo, grey flannel trousers, white sneakers
A navy long sleeve knit polo, grey wool flannel wide leg trousers, and white leather sneakers. Maybe tuck the polo in and leave one button open, or don’t. It’s the same easy shape as these navy wide leg pants outfits, dressed down with sneakers.
The tell: look where the sleeve meets the body. Small slanted stitch marks running beside the seam are fashioning marks, and they mean each panel was knitted to shape. Cut and sewn knits have a plain seam, which is fine at a lower price and a little less likely to hold its shape.
Cotton or merino on the tag is the version to hold out for. $15 to $30.
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Where to start
Nine outfits, and most of them come down to one collegiate piece over plain denim or chinos. If you only hunt one thing first, make it the rugby shirt. It carries an outfit alone and the tells are quick to check.
There’s more in the old money outfit ideas archive. Whether you pop the collar is between you and your conscience.
