Splurge or Save: A Classic Preppy Look

My trip through parts of New England last week has me thinking about all things preppy. This week’s splurge vs spend outfits contain a few quintessentially prepster items that can blend into many style recipes. This classic, preppy outfit with penny loafers is a timeless look you can create at all price points.

It doesn’t get much preppier than a great pair of penny loafers. Remember when we actually put a penny in the front? I found the history of the penny loafer fascinating. They’re a versatile and unpretentious shoe that seems to transcend time. They look as cool today as they did when Elvis wore them.

affordable outfit with penny loafers and breton top

I paired them with simple chinos, a Breton tee, a sweater blazer for comfort, and easy knot stud earrings. I kept the accessories tonal for a very understated look.


The pieces are less expensive in the save outfit, but not all are budget-friendly. The splurge outfit is a mix, and many of the items are marked way down, so the total would be much higher at full price. If you have a classic wardrobe, this would be very easy to recreate from your closet.

The save outfit comes in at $563.79, and the splurge is just around $1138.45.

I always ask my husband if he can tell the difference simply by looking a the photos, and he nailed it right away. Is there an item that instantly tips the scale for you?

Did or do you wear penny loafers?

Thanks for reading, and remember to wear what makes you feel confident.



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  1. Cath🇨🇦 says:

    I have a classic Penny loafer story… from 1966. Three of us , all Vancouver teens, drove across the border to Bellingham WA for a quick trip. This was my first time in the USA 🇺🇸 , so I was quite excited. I chose a pair of brown leather Penny loafers. On our return, we stopped at border control, and I told my friends that I had “ to declare” my purchase. Lots of eye rolling and sighs! No problem of course, and I wore them with American pennies ! So proud of my purchase !

  2. Well, I couldn’t spot the more expensive outfit. If it’s worn on the golf course, tennis court or at the country club it’s not in my wardrobe. I do like a classic leather loafer, though.

  3. I wore the penny loafers. I may wear them again. How would I decide on which is the more expensive outfit? It is the blazer. I really like the comparison post. Thanks

  4. Shellia McCormick says:

    I’m building a new wardrobe a few items at the time with what I see, usually on this post. I just ordered two blazers and one pair of pants. I’ll get my own shoes, I don’t trust purchasing them online. I’m so grateful I found your site. I’m finally feeling a little more classy. Thanks Jennifer!!!

    1. Shoes can be tough unless you really know the brand. I’m glad you’re enjoying the posts.

  5. This was a fun comparison! I love Bretton shirts and own quite a few – ditto for chinos. I like the Bretton top w/the chinos and the jacket w/the chinos but not the jacket w/the top. I’d choose navy or royal blue. To me, penny loafers are like Topsiders: you’ve worn them for years or will never wear them. There’s not much from high school that I’d wear now.

  6. I loved my penny loafers 👞 which I Changed over to dimes in High School.
    I love the Bass loafers and may have to purchase a pair this year just for nostalgias sake.
    Really like the splurge or save segment. If you shop smart you can look awesome and save enough for 2 outfits instead of one.
    Thank you for your wonderful posts.

    1. Dimes! That’s cute. You’re so right about saving money and looking great.

  7. For me, the giveaways are the finer detail on the stud earrings, the crisper tailoring on the blazer, and the obviously superior croc-embossed bag. I have a Breton striped boat-neck tee from the Gap which is literally decades old — I still love and wear it. I often put together an outfit similar to this, right from my own closet, substituting a khaki safari jacket from Talbots which, again, I’ve had for decades! That’s the beauty of a classic wardrobe.

    1. Exactly why I love classics!

  8. Of course I wore Penny loafers, my name is Penny. My dad bought them for and put the pennies in. I wear much of this look often. Yes the St James bretons are more pricy but very worth the splurge. I have the classic boat neck.

  9. I love these splurge or save posts, Jennifer. The handbag gave it away for me. Very nice comparable outfits. I love the preppy look. Bodes well for my classic, comfortable style.

  10. Yes, I wore penny loafers. As for the post, it was an immediate look to know the pic on the left was the most, from the jacket, to the T, earrings, purse to the watch. Enjoyed the post. The stripe of the T was a give away.

    1. The stripe! Interesting. I have to go back and look now.

  11. I have never been a sneakers person. In the 90’s commuting to Manhattan, I reached back to my school days and purchased a pair of Weejuns. Negotiating the streets of Manhattan became easy, and keeping with the Corporate image, the loafers were right on.

  12. suzanstew says:

    I like the idea of trying to figure out which is which. The gold medallion on the handbag gave the splurge away. I love this outfit and have long wanted a Brahmin handbag. Handbags are one thing I have a hard time purchasing. I anguish whether I will really use/need a new handbag. My mother left in me a strict sense that only leather handbags are acceptable so what I look at is limited.

    1. Shellia McCormick says:

      I have the handbag problem, too. I love them so much I have way too many, so I don’t use them for too long before I buy a new one. It’s hard to spend lots of money on something I know I’m only going to use a short time, I’ll come back to it eventually, but I keep them simple and cheap(er).

  13. I wore penny loafers for most of my school years. When I was in the lower grades we put pennies in our loafers. By the time I got to high school all the cool kids put dimes in their loafers. If you needed to use a pay phone you were all set! I spotted the splurge instantly; the handbag gave it away.

  14. I love the preppy look. I always have a Breton shirt in my closet. I did wear the Bass Weejuns penny loafers in high school, but they were always tight and hurt my feet. I wore them anyway. If I could find comfortable ones, I would buy some now. I have a wide foot, so shoes are sometime hard for me to fit.

  15. Janice in Ky says:

    I love the splurge and save post. On my retired budget I’ll be shopping the save side of the post 😊. I’ve always liked the classic preppy look. Have a pair of bass loafers that are at least 25 years old, mine are black and brown. The Brahmin handbag was the give away for me.

    1. It’s hard to beat great quality timeless pieces 🙂

  16. I really love these posts! The telltale item for me on this one was the St. James breton tee. They are my favorite. Interestingly, I like the Quince blazer better than the more expensive one! This whole look is up my alley. Thanks for doing these!

    1. I’ve had my eye on the St James Breton for a while. Thanks for the review. Which neckline is your favorite?

  17. I love this look! I picked the more expensive right away. The jacket, top and earrings gave it away for me. They look more polished.
    Please keep doing these comparisons. This is my favorite post each week.

    1. I’m so glad you like these too!

  18. I love this look. I’ve always worn preppy clothes. I’m a sucker for a good striped top. I’ve worn penny loafers all my life. We wore them in grade school with our school uniforms. So comfortable!

    1. I’m going to have to try some on again. It’s been years!

  19. I like the less expensive blazer. The sweater blazers are something I love. They feel cozy. I had a Ralph Lauren similar to the splurge. I ended up donated it because the pocket were so bulky. I prefer a slim leg pant instead of a straight leg pant. I do enjoy you posts.

  20. I absolutely love this look! I am retired and on a fixed income and so appreciate the more economical options; please do more of this! Thanks!

    1. I will keep them coming.

  21. Thank you for the research you do for these comparisons. I enjoy these articles. I picked the outfit on the left because the earrings look substantial, the jacket, and the Brahmin bag.
    Love this look!

    1. I searched hard for a Brahmin alternative but they’re pretty distinctive. Banana Republic has some gorgeous brown Croc-embossed bags this fall. I’ve got my eye on this one.

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