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This is our latest in an occasional series on weekend clothes with a specific personality — see all the posts in the series here. Today: how to get the preppy look, and the best brands for preppy clothes.
As a reminder, there was an old book Kat had where the author (’90s-era CNN style commentator Elsa Klensch) talked about how “[m]any successful businesswomen I know tap into their private visions of themselves and express that inner being in their weekend wear. … On weekends, I want to be softer, more romantic. My fantasy in the summer is to look as though I just stepped out of an F. Scott Fitzgerald novel wearing Gatsby-style long skirts and gently flowing chiffon scarves.”
Accordingly, we thought it might be fun to round up different stores selling “weekend vibe” clothes in different personalities for our ongoing Weekend Wednesdays series.
After all, we’ve talked in the past about the weekend you vs. the weekday you — as well as shared our best tips for upgrading your weekend clothes and cultivating style in general. We've taken a look at how to get the boho look and tough girl chic — and especially now that the warm weather is here, it's the perfect time to share the best brands to shop for preppy clothes.
More so than the previous two looks, preppy styles are more likely to do double-duty as weekend wear and workwear (with limits, of course), so many of the brands below are good bets for both.
Building Blocks for the Preppy Look
The preppy look is more than just having a few pieces from preppy clothing brands — these are some of the defining characteristics:
- Classic prints & fabrics & colors: pinstripe/stripes, florals, polka dots, plaid, Madras, gingham, tweed, seersucker, cable knits, pastels, navy blue…
- Dresses from Lilly Pulitzer, Eliza J, Ted Baker, Ann Taylor, Brooks Brothers/Red Fleece, Boden
- Cardigans, specifically buttoned, banded styles
- Shoes: Oxfords, loafers, slingbacks, boat shoes, classic pumps and flats, moccasins, riding boots — try Tory Burch, J.Crew, Kate Spade, Trotters, Boden, sometimes Talbots
- Little details: ribbon trim, bows, pompom trim, tassels and metal hardware on shoes, blazer linings with prints, etc. (headbands and scrunchies are back, although you may want to see our last discussion on hair accessories for grown women)
- Weekend/resortwear: Vineyard Vines, Trina Turk, J.McLaughlin, Jack Rogers, Tuckernuck, Sue Sartor
Preppy Workwear We've Featured Recently
Stay tuned for a roundup of preppy workwear we've featured recently!
The Best Brands for the Preppy Clothes
Lilly Pulitzer
It makes sense to start with Lilly Pulitzer, the designer known as the “Queen of Prep.”
The brand is known for bright, colorful floral/tropical prints, and their offerings include beachwear and resortwear. Here's the story behind those prints, from Pulitzer's 2013 obituary: “A rich housewife with time to spare and a husband who owned orange groves, she opened a juice stand in 1959, and asked her seamstress to make dresses in colorful prints that would camouflage fruit stains” (as you do).
Lilly Pulitzer pieces are perfect for vacations, baby showers and the like, and brunches — you'll look like you should have a mimosa in your hand. (The bright colors are so fun that as a totally non-preppy person, I bought this one a few years ago.)
You can find tons of Lilly clothes and accessories at Nordstrom and Zappos, as well as the brand's website.
Tory Burch
pictured above: one / two / three / four
Tory Burch is a stalwart for preppy clothes! You can find Tory Burch at Nordstrom, Neiman Marcus, Bloomingdale's, and Zappos. The brand (whose popularity is part of the reason Tory Burch is a billionaire) is a great choice for feminine pieces with lots of stripes, florals, and other preppy patterns, occasionally accented with details such as ruffles, scalloped edges, embroidery, etc.
Be sure to also check out the bags and shoes (we featured the brand in our best work bags and comfortable flats for summer posts), as well as other accessories. And since this is a Weekend Wednesday post, we must direct you to the brand's fun, pretty swimsuits.
(Note that Tory Burch clothing is pricier than the first two featured brands.)
Tuckernuck
We should do a full roundup of Tuckernuck, but since they've come onto the scene they've been a reader favorite. Do check out the Jackie dress, one of their bestsellers (pictured above).
Great Accessories If You Have Preppy Style at the Office
Pearl Jewelry
Stay tuned for a roundup of some of our favorite pearl and faux pearl necklaces! In general (as of 2024) if you're looking to invest, Mikimoto has great quality pearls — and note that between 7mm – 8mm is the most common size, so try to copy that if you're going faux. (One possible source for faux pearls: this Etsy shop.) Some pearl jewelry we've featured recently include the ones below…
Twinsets
Some of our favorite classic cardigans for the office as of 2024 include those below — definitely check Talbots and J.Crew Factory if you're looking for plus sizes, and Quince is always a nice affordable option. Veronica Beard and Brooks Brothers both keep a bunch of options in stock.
Loafers
As of 2024, some of our favorite loafers for work are from Sam Edelman, Everlane, and Madewell. If you want something more classic, readers love Sperry and Ferragamo; if you want comfort, Vionic and Dr. Scholl's both have options. Meanwhile, if you want something a bit more feminine or slouchy, the Tory Burch loafers are all really highly rated at Nordstrom (especially this “ballet loafer“)!
Classic Pumps
Hunting for comfortable work heels? We've got a whole guide just for that, but some of our favorites include Marc Fisher LTD, Sam Edelman, M.M.LaFleur, and Cole Haan. On the pricier side, check out Ferragamo, Stuart Weitzman, and Sarah Flint. For comfort-first styles, look to Vionic, Sofft, and Naturalizer.
Kitten Heels
As of 2024, kitten heels are having a moment! Nordstrom has a bunch right now from brands like Sam Edelman, Franco Sarto, Open Edit, Dolce Vita, Jeffrey Campbell, and Steve Madden. Looking for something fancier? Check out Sarah Flynt, Stuart Weitzman, and M.M.LaFleur.
Classic Flats
Some of our favorite comfortable flats for work as of 2024 include M.M.LaFleur, AGL, and French Sole. On the more affordable side, check out Rothy's, Sam Edelman, and Rockport. We've also rounded up the best loafers for work, and our favorite sneakers for work outfits!
Mary Jane Flats
Our general favorite Mary Jane flats for work in 2024 include J.Crew, Loeffler Randall, Dolce Vita, Rothy's, and Sam Edelman. We also like comfort-first styles from Rothy's, Vionic, and Dansko.
Riding Boots / Flat Knee-High Boots
Hunting for black knee-high boots? Here are some of our long-standing favorites as of 2024 (pictured below). HEELED knee-high boots are starting to trend again, also — some of the best looking options include these from J.Crew, Everlane, Veronica Beard and Stuart Weitzman (not pictured).
Headbands
Stay tuned for a roundup of our favorite headbands — in the meantime check out our roundup of easy office up-dos, as well as our post on hair accessories for grown women!
How about you, readers — what do you think are the best brands to shop for preppy clothes? Do you consider your style to be preppy, or far from it?
cbackson
I think Lilly is pretty out, at least in ATL. 5 years ago all you saw at church/baby showers/the pool was Lilly, and now I don’t see it anywhere. Still some good finds at Brooks Brothers (especially if you want preppy/WASPy accessories), and I wear a fair amount of LL Bean Signature as well.
Housecounsel
I don’t wear Lilly – it just feels too froufrou to me – but I think it’s pretty classic. I don’t think of it as something that goes in and out of style.
Anonymous
Ideas for my nephews 18th birthday? Budget is around £100 and he’s going to do an apprenticeship most likely not university so he’ll be staying at him after high school. No particular hobbies but plays a big of golf, football, pool etc. He doesn’t really support any teams. Thanks
Housecounsel
My husband would say never to buy someone golf equipment. He needs to choose his own. Can you pay for an outing to a football game or a round of golf for him and his friends?
Anonymous
I need to stop seeing my personal trainer. I’m paying $170/mo for a weekly 30 minute session, and I’m not getting much out of it for that cost. I’m not seeing results, I don’t have time to weight lift on my own (I also do 2 hour long group exercise classes that are included in my additional membership). She is really nice and motivational, though, and I don’t know what to say? Maybe that I have other bills to pay? I’ve been going since the fall. I don’t know why I’m stressing over this, but I feel awkward.
Anonymous
Hey, thanks for all your help. I need to cancel lessons going forward.
BeenThatGuy
I’m a fan of a text message for this situation. Simply stated: “Tomorrow will be my last session. Thank you so much for all you’ve helped me with. I wish you all the best. See you around the gym!”
lulu
Tuckernuck is the place for preppy dressing IMO!
Anonymous
I am planning on getting a puppy at the end of August (french bulldog). I chose the breed because they are well suited to apartment living and don’t need a ton of exercise – I live alone in a one plus den and am a 2nd year associate at a midsize firm (approx 200 lawyers). I have planned and researched for a puppy for years and years, but never pulled the trigger because I was waiting for a boyfriend to help me raise him. I’m now a year out of a really terrible breakup, am not really dating, and have decided that I don’t want to have my life on hold while I wait to find someone. My therapist also suggested it would be a good idea for the companionship and to help with my anxiety and depression (for which I am now medicated). All of this is just background, as I am wondering if anyone has experience raising a puppy on their own while working a demanding job? I know it is going to be really tough for the first while, but I live a 5 minute walk away from my office and have a good support system in place (three brothers with flexible schedules and parents eager to puppysit when I have a busy week or go away). Any tips for surviving/not losing my job while I am training the little guy!?
Anon
omg no this is a terrible idea. Getting a dog is a great idea, getting a puppy is not. Having a puppy is really not that different than having a newborn human – you’re up all night dealing with them, they’re not housetrained (and diapers aren’t really a thing for dogs), they chew on everything and destroy your stuff, they can’t communicate and cry all the the time, etc. Why not rescue a young adult that is already housetrained and will be so much less work? There are breed-specific rescues if you want a specific breed.
Anonymous
OP here. Several reasons: 1) rescue shelters will not give me a dog as soon as they hear I’m a single lawyer; 2) raising a puppy allows them to become accustomed to your lifestyle almost from birth, so will be way more manageable than getting a dog that already is used to constantly being around other dogs/people/with a backyard/etc.; 3) I have a puppy playpen, crate and a hands-free leash to reduce the amount of destruction from his chewing and have otherwise puppy-proofed my home and 4) housetraining will certainly be the hardest part, but it only took our family puppy about 2 weeks and then he was fine; 5) getting a puppy from a breeder makes it much easier to check for genetic defects and temperament issues (especially with a breed like frenchies that is so prone to illness, genetic issues and allergies).
Wildkitten
Municipal shelters are generally less b*tchy than private ones. Puppies are seriously the worst.
babyweight
FWIW – Agree re municipal shelters. Dead easy. I was a single lawyer at the time. My municipal shelter let me have a 1 year old house broken mutt. He’s wonderful and he has been with me for over 14 years now. Best decision I ever made. (Don’t tell my husband ;) ). I’m a huge dog person, but I have never gotten a true puppy. The 6mo – 1 year old range has worked out well for me.
cbackson
I got a puppy (5 months old) as a senior associate in biglaw. Like you, I lived 5 minutes from work, which really helped. What I did:
-Got a slightly older puppy
-Worked from home for the first week after I got him, so that I could get him over the hump in terms of housetraining. In part because of his age and living situation, he was borderline house-trained already, so that was fairly fast.
-Hired a dog walker to come twice daily so that he was getting potty breaks every 3 hours until he was old enough to only need one potty break during the workday.
-Hired a trainer who came and worked with him at my house and also worked with me and him together. Expensive, but totally worth it.
-Limited his “range” to my kitchen until he was fully housetrained and no longer chewing.
-Started twice-weekly daycare once he was fixed.
Getting my dog was the best thing I’ve done for myself in the last five years – it was (and is) a ton of work, but he’s totally the joy of my life and my best buddy.
Shananana
So, near where I live, there is a doggie day care that has a 5 day a week puppy program that focuses on socialization and training with a discount because they are there every day. It is literally the only thing that would make me consider doing a puppy again, and I had a pretty chill puppy the first time. If that is not a possibility, get a dog walker and sign up for training classes and mean it.
Also, if you are picking a puppy from a litter, my best advice I give is pick the opposite from what the dog books tell you. You want the quiet one who comes and sits by you, not the curious adventurous one. Yes that one is probably objectively smarter, but for apartment living you want a dog that is more laid back and relaxed. I got my dog in my mid twenties as a puppy and he will be twelve this year. We’ve been through a lot together, most all of it with me single, and I give a lot of credit to picking the calmest puppy in the litter. Lots of people will try to talk you out of it, but I went into it knowing it would be difficult, but this decision was for his life and I would do what I needed to do to make it work.
Anonymous
I got a rescue dog who was advertised as 6 months old, but my vet estimated her age at 10 months from growth and teeth. She wasn’t housebroken, at all, but the good thing about an older puppy is they can hold it a little longer. I live 10 minutes from my apartment. I would let her run around the yard for a good 30-45 min. in the morning and an hour after work. I went home at lunch for an hour to let her out, and I crated her while I wasn’t home for many months. Even today, I feed her in her crate so she has happy associations in her safe place. I call it her “house”. If I say “go in the house”, “breakfast/dinner in the house”, she runs right in. She’s about 4 now.
SMC - San Diego
Like cbackson, I have had puppies (twice 14 years apart) while working a full time job and I second her recommendations. The key in my case was (1) I set up an area of my house with access through the dog door to my backyard and absolutely nothing he could destroy and then used an x-pen to block that off from the rest of the house; (2) walk in the morning, two during the day, another in the evening – fortunately I live in a neighborhood with a million teenagers who were thrilled to play with my puppy; and (3) worked from home or had a full time dog-nanny (my Mom) for the first week due to house training issues. Lot of exercise plus limiting the options to destroy things got us through the puppy months.
Also, I do not know about the rest of the people making recommendations, but a puppy is not fully vaccinated until four months and my vet highly recommended avoiding any type of group setting with dogs I could not verify were vaccinated until then. (We have a lot of parvo in our area.) There were some puppy socialization classes, but none of the training classes started before 6 months.
Wildkitten
Does anyone have a favorite career coach in Chicago?
Anon
Vineyard Vines.
Anonymous
I think you pretty much nailed the list. I would add Hobbs, Joules and Jaeger.
ITLady
Can’t have a preppy Roundup without including Brooks Brothers. Lands end, Vineyard Vines, and (to an extent) J Crew are where I shop the most. Ralph Lauren used to be my go to for OCBDs but they moved to alpha sizing and they fit me like crap.