Just to clarify, my family doesn’t have a boat. We don’t belong to a country club, and we are hardly American royalty. (Although, we do have a castle in Ireland…or had a castle in Ireland…Long story.)
Really, I’m not sure from where my obsession with the stereotypically “preppy” look came. I’ve always gravitated towards prep-school staples in nautical hues. (I attended a private Christian school, but sadly, no uniforms. I was probably the only person who wished we had uniforms.)
I think maybe I can point to a combination of Gossip Girl and J.Crew as the catalysts that pushed me over the preppy loving edge. As an aspiring YA author, I devoured the entire Gossip Girl series and waited with baited breath for the television show. Blair Waldorf quickly cemented her spot as the Queen B of my style loving heart. I loved her school girl inspired pieces in classic colors. (And, I also loved that when I re-watched the first season years later, she still looked stylish.)
Then, I started working at J.Crew to make some extra money during college, and I learned the art of layering from dressing countless mannequins. Now, I possess a closet that is 50% navy, 25% red, and 25% black. Everything I own can be mixed and matched and will always look pulled together. I’ve fixated more on quality and staying power of my clothing, versus freaking out over every new trend. (And, when there’s a trend I kind of like, I buy it in a classic color that I can wear for the next few years.)
Interested in pulling together your own classic wardrobe, but not sure where to start? Let me be your guide!
The Classic Blazer. Fit is important here, and if you need to, buy a size too big and have it tailored to your body. I recommend navy because it works year round in both the office and on the weekends. In the summer, it can make a sundress work-appropriate or in the winter, it can be worn over sweaters for a cozy layered look. This will also be an investment piece that will get a ton of wear, so be prepared to spend at least $150. The whole point is to have this for years!
Look for: Navy. Plaid. Black. Gray. Herringbone. Tweed. Camel.
The Sweater. I prefer cardigans because I think they are easier to layer, but this depends on your personal preference. The kind of knit matters too. If you’re always hot, then stay away from heavy wools and look for thinner cotton blends. I don’t spend a lot of money on my sweaters unless they’re really special. (One of my favorite things to hunt eBay for is vintage wool sweaters with animals!) Also, I recommend to stay away from J.Crew sweaters unless you’re getting their cashmere. Almost every sweater I have from J.Crew has holes in random places (as compared to my cheap Old Navy versions that last forever). Plus, I’ve noticed that Gap and Target many times will copy-cat J.Crew’s cutest designs, which is a win for our wallets!
Look for: Your favorite colors! Show your personality with bright colors or prints, but make sure that they can integrate easily into the rest of your wardrobe!
The Oxford. Button down shirts are your very polished best friend. Like a blazer, they can be dressed up and layered for both work and the weekend. While investing in a few basic colors (like white or navy) is great, I really love bright, happy patterns (like gingham, plaid, or even leopard!) I rarely wear an oxford all by its lonesome, so look for options that have great detail on the colors and sleeves.
Look for: Classic colors and prints. Polka dots. Gingham. Plaid.
The Bottom. Whether you prefer pants or skirts is a matter of personal taste. I’m super tall (5’11!) and I have the hardest time finding pants that fit properly. So, my solution is to wear skirts (or dresses) all the time. It’s to the point that I’m actually more comfortable when I’m in a skirt than when I’m wearing jeans. (Plus, you have the added bonus of always looking polished.) The same rules apply to both pants and skirts—fit is important. Nothing too short or tight. Like with the sweaters, look for what makes you happy, but make sure you have a few options in your classic range of colors.
Look for: Classic cuts. Classic colors. I tend to not like patterned pants since they’re usually not super flattering, but patterned skirts are a win! (Weird how that works…)
The Shoes. Shoes are definitely a matter of taste, but luckily there are several different options that all retain their classic appeal. Remember, don’t look for what’s “trendy”, but for what you can wear over and over. I usually wear Tory Burch Reva ballet flats or Sperry’s loafers and boat shoes. I think the boat shoes are better for weekends though—if you want a good work shoe, I would look for loafers or ballet flats. In the summer time, there’s nothing like a great pair of Jack Rogers.
The Rest. Once you’ve assembled all your building blocks, you may start to see certain colors or styles become dominant in your closet. When your aesthetic is pinned down, you can start expanding to accessories. Because I have so much navy, I don’t like to carry a navy purse. Instead, I’ll grab a bright red or deep camel color for contrast. Personally, I don’t like wearing a ton of jewelry, so I usually wear the same pearl necklace and gold watch every day.
Thanks Tierney! I'll be back Monday with our regular scheduled programming!