1) Striped tee. I own three of these (black and white, yellow and white, and navy and cream) and find them to be incredibly comfortable and versatile. Nautical stripes are timeless, whether you're landlocked or on a boat, and this particular rendering is a chic European spin on the all-American t-shirt. Breton sweaters are lovely, but I prefer lightweight tees that can be worn in layers year-round (and find three-quarter sleeves to be the most flattering).
2) Riding boots. If your climate is even remotely chillier than tropical, you should own a pair of flat riding boots. They pair perfectly with dresses, leggings, jeans...even shorts in spring and early fall. Simultaneously athletic, bohemian, and classic, they are a true gift from the shoe gods.
3) Trench coat. What girl doesn't secretly want to embody even the slightest suggestion of Audrey Hepburn in Breakfast at Tiffany's? I prefer classic khaki, but I've seen beautiful renditions in every color, from periwinkle to punchy red. Waist-nipping, trend-proof and fabulously mysterious, the trench flatters literally everyone. Even better, it can be worn with nothing underneath for, uh...special occasions.
4) Aviators. Max Potter just walked into the coffee shop I'm at right now. She is wearing Ray-Ban aviators. 'Nuff said.
5) Two-tone men's watch. If you don't know by now that I'm obsessed with watches, you're either a first-time visitor or an Alzheimer's patient. Since I wear both gold and silver jewelry, I go for two-tone. And a men's watch looks fierce on a woman's wrist. Always has, always will.
6) Black high-waisted skirt. My shopping weakness. The item I will never be done buying. Seriously. I own, like, six; I could easily go shopping today and come home with an armful more. Of course there are variations - one is studded, one is leather, one is elegant and tulip-shaped, one is dangerously curve-hugging and reserved for when I need to pull out the big guns - but collecting black skirts of every silhouette and embellishment has become a sort of shopping sub-hobby.
7) CZ studs. Diamonds are a girl's best friend, but cubic zirconia is a broke college student's best friend. I'm not much of an earring person (I'd rather wear a big, colorful ring or a statement necklace), but I think bare ears (if pierced) look unfinished, so I usually default to these. A little sparkle above the neck makes for a more polished look without detracting from the rest of the ensemble.
8) Blue button-down. Crisp white shirts get all the praise, but I prefer pale blue - it's slightly off-kilter, doesn't show dirt, and is still neutral enough to wear with most other colors (my favorite combos being blue and gray and blue and peach). I like to roll the cuffs up to right above the elbow and wear it tucked into a high-waisted skirt, with skinny jeans and riding boots, or open over a dress in place of a cardigan.
9) Nude platform sandal. I refuse to buy shoes with spindly heels because I know I won't wear them, so when it comes to height, platforms are my best friend. A flesh-toned shade lengthens the leg line and can be worn with just about anything, day or night. These are by Prada, my favorite shoe designer/where all of my money will be going once I am employed full-time.
10) Flirty dress. I'm a sucker for anything silky and ruffled. A dress like this takes you from the the office (skinny belt and a cardigan) to a dinner date (strappy heels and loose hair) to drinks with girlfriends (stacked platforms and statement jewelry).
Runners-up: A quilted purse, a well-cut blazer, a yellow belt, a giant cocktail ring, and (sigh) perfect jeans (dark and skinny).
My basics are very revealing of my personal style: hyperfeminine, with a grounding in French classics (and ill-suited to cold climates) (FML). As all over the map as my outfits may be from day to day and season to season, these are the things I keep coming back to time and time again (and, quite honestly, the things I would wear every day if people wouldn't judge me for, you know, wearing the same thing every day). I'm all for experimentation, but it's always nice to have an understanding of what makes you tick deep down inside. Give it a few minutes of thought. The items you choose may surprise you.