What You Will Always Find in My Closet

What You Will Always Find in My Closet

no matter what time of year it is…


The 1980’s and stumbling into prepdom…I grew up in Northern Illinois at the height of prepdom in the early 80’s and early 90’s. What was merely reserved for the East Coast prep school elites had emerged as the way to dress for the fly over states—even if my parents did it unknowingly. They never read The Preppy Handbook and they didn’t go to prep school, but collars, madras, and Bermuda shorts were in their closets. The Gap, J. Crew, and our upscale department stores, like Vonmaur, had made preppy clothes accessible without a trip into the city—by city I mean Chicago. Of course, a trip to the city was going to happen eventually because of the Marshall Field’s (sigh).

It was a time of the middle class joining country clubs, like my parents did, to golf and socialize. You couldn’t be on club property without a collared shirt or a pair of chinos. Dinners at the club had a dress code to follow and yes we had to wear stockings with our dresses and skirts. Wearing polos, oxfords, tennis sweaters, and penny loafers were not only what we were taught to wear by our parents, but what became popular in our schools. I fully embraced it and haven’t veered from it much since.

When I was in middle school, my mom found old Seventeen magazines from the 1960’s and it unlocked a whole new world of prep to my all too eager eyes. Ivy League photo shoots of girls clad in wool tartan top to bottom. Turtlenecks, cardigans, and tights. I mimicked this look in my own wardrobe proudly wearing my newly found vintage wares to school and tying ribbons around my ponytail. Then, I saw Ali MacGraw in Love Story and wanted to attain her wardrobe.

I’ve never considered myself a fashionable person, just someone who knows what I like. Now in my 40’s, I can honestly attest to the fact that prep is always going to be my favorite way to dress. It’s forever classic and I feel like some of the things in my closet have been in my closet for ages and they are quite timeless indeed. I have even more appreciation for this way of dress now that we live here in New England. It fits the seasons and activities so well. The art of layering definitely comes in handy here too. I guess I have my Mom and Dad to thank for all those failed golf lessons and country club dinners to help me cultivate my version of preppy style.

Had to share here what I put on Instagram Stories…One of my sweaters from high school…bought at The Gap in the Men’s Department (as was common for us girls to do). Just buy a small or steal your boyfriends ;). It didn’t matter how big it was because…

Had to share here what I put on Instagram Stories…One of my sweaters from high school…bought at The Gap in the Men’s Department (as was common for us girls to do). Just buy a small or steal your boyfriends ;). It didn’t matter how big it was because you were putting it over your polo or oxford anyways.


Wardrobe pieces you will use all year long that will become the foundation of your classic style.

The foundation of a classic closet…I thought today I’d share some classic staples that appear in my closet no matter the time of year. I sat down and dissected my closet to find that certain items are always there no matter the year or the season. Is it 1983 or 2020? Fall or Summer? They are good foundational pieces if you live somewhere with all the seasons and you can build off the basics once you invest in them.


The Ralph Lauren Cotton Oxford

This is hands down my favorite oxford not because of the label, but because of the fit and how it hangs. It’s probably one of the most worn shirts I own and I have it in several colors. If you want to add this to your foundational wardrobe I’d start with one blue and one white. You can eventually build on that with adding a pinstripe or a pop of color like yellow or pink. I use these shirts all year long. In the spring, they are nice enough to wear alone with pants or jeans or tied at the waist over a sundress. In the summer, unbuttoned over a swimsuit for a cover up or paired with shorts. In the fall and winter, under a sweater or cardigan.

Ralph Lauren Cotton Oxford available here


The L.L. Bean Cotton Cable Knit Sweater


Mom always said, “Don’t forget your sweater!!” The cotton cable knit or fisherman sweater is the perfect layering piece. (Save the Shetland wool version for fall and winter—wink, wink!) Perfect for: On Nantucket in spring and summer when the sun is out of sight. It can get chilly at a moments notice so keep it in your bag or bicycle basket. It’s fall and you are leaf-peeping in Vermont and then head to the apple orchard with that crisp autumn air. Your sailing off the coast of Maine and it’s overcast and breezier than you expected—even in the summer. It’s winter and your getting your Christmas tree in Connecticut with a family photo after—matching family sweaters optional. It’s versatile enough to throw over your shoulders in the warmer months and perfect over that oxford we just mentioned in the winter months. This is one area where I am less discriminatory when it comes to brand. I say invest in the best you can afford. Growing up, we had Land’s End or Gap sweaters and they lasted just fine. Nowadays there are so many to choose from I’ll just give you my favorites. My tried and true favorites are: L.L. Bean and a close second Land’s End.

L.L. Bean Cotton Fisherman Sweater available here

The Navy Cardigan


Navy to me is a neutral because it goes with EVERYTHING. It goes with brights, it goes with earth tones. It goes with all white. I’d spring for one with the ribbon sewn along the placket (edge with button holes) so it lasts longer. Cashmere is a great investment and gets better with time, but a mid-weight cotton is a great staple too. Perfect all year over tanks, oxfords, and dresses. My favorites are from Brooks Brothers and Land’s End.

Land’s End Cardigan

Brooks Brother’s Cardigan

I also really like these with a white trimmed collar or letterman style stripes on the arms.


Your Favorite Denim in 3 Rinses

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Shopping for jeans has become a smorgasbord of different leg openings, different waist heights, and different washes. It honestly is a bit too much for me nowadays. I’m not a torn denim person, I’m not a hop on the new jean trend person. My advice for a great foundational closet is to find that one pair of jeans that fits your body without all the trends. Whatever that cut is skinny, boot, straight leg or high waist or mid waist. Find what flatters you and buy 3 rinses (Mid rinse, dark rinse, and white) in that jean and try to get a couple pairs of each rinse eventually. They could be expensive or mid range. I have been super happy with the Gap High Rise True Skinny. They break in nicely after a day of wearing them and I can go a few days of wear before I have to wash them and they form to my shape. Since I am tall they have a great tall length and I find this cut flatters my shape best being an average sized gal—not skinny, not curvy.

A Chino Pant

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Since we are talking foundational…I’ll stick to khaki chinos—plain front, plain back—only pocket slits. Again…they are cut all different ways these days so finding the one that flatters you is key. I like them to be looser in the legs so I can roll the ankles up in the spring and summer. There are different weights too, but a mid-weight is a good starting off point since you can wear it year round. I find the lighter weights show pockets too easily. For me, the Gap usually is my go-to’s for chinos. I can get tall lengths so that is the selling point for me.

A Solid Dress Pant

I’m not veering into work wear in this post, but there are times or places where I want a dress pant. Same rules apply for me as before stated when I shop for one. I’d stick to an earth tone or navy pair for your first purchase so it can work with your other foundational pieces. I am a big fan of a red dress pant, so that would be my one suggestion if you don’t want to stay neutral. I do like to have them flatter, of course, and just above the ankle are cute with heels or flats. You build on your basic colors and add in patterns to suit the season.


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G.H. Bass Weejuns

Footwear to me is one of those categories that is really seasonal. There aren’t too many pairs of shoes that I don’t rotate out with the season. There are exceptions though and my Weejuns are just that! I can wear them with pants and even shorts or a skirt. They are very versatile and always look nice. I love the classic look too. Penny loafer or tassled. Eastland makes a great penny too, and it’s not as expensive. I have both in my closet.

A Neutral Pointed Toe Flat

These can be all year round if you buy the right one. They are super flattering and elongate the leg. Again, we are talking foundational. You can always add that super cute plaid one around holiday time. Look for matte leather in a nude color. No patent leathers or wovens. You can tell by the material whether or not they can be year round. A great one to invest in is Sarah Flint NYC, which I need to do soon because my pair from Sam Edelman flats have seen better days!

A Nude Heel

No matter what time of the year you find yourself in, you will want a nude heel. It doesn’t matter. Even in summer there will be an indoor wedding at some point when the only thing that matches your dress is a nude heel. They work for pants and dresses. Not too high, not too low. Stick to matte for a starter.


The Trench Coat

Again, outerwear is one of those categories that is completely seasonal, but one coat I always have handy no matter the season is my trench coat. It gets a lot of wear in spring, fall, and even early winter sometimes. It’s a forever classic.



I keep it simple most of the time. Earrings and maybe a watch if I’m out and about. There are 3 earring styles that are my go-to for everyday. Stud earrings are a staple and I wear the most out of my pearl, diamond, and gold knots. I’m a fan of the statement earring too, but those are my three that are perfect for everyday.

These are my suggestions if you are starting a classic wardrobe or just want to invest in something that is tried and true. There are options for every budget, but I think you should check quality and try to invest in key pieces that will last. I think we’ll expound off of this post and do some seasonal classic style posts too.

There’s more I could add, but I wanted to nail it down to those pieces that are used year round and are great things to build off of for a more diverse wardrobe.

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Stay safe! Next time I do a classic style post it will be about summer staples.

Until next time,


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