Black Pumps
If you only invest in one pair of shoes in your lifetime, ensure it's a pair of classic black pumps. A quality pair with just a high enough heel will last for years. Plus, you'll be able to wear with everything from a party dress for a night out like Kim Kardashian, or with a pencil skirt and blouse for work.
George likes: Manolo Blahnik pumps, $595
Straight-Leg Jeans
Go-to jeans are a must—especially when they're made of simple dark denim cotton and free of anyembellishments so that will last for more than just one season. Test out a skinner style that hits right at the ankle like Julie Bowen's to make your legs and silhouette appear longer. Invest in a quality, more expensive wash to ensure the color won't fade quickly.
George likes: Acne Flex Raw Demin, $200
Classic Sunglasses
Embrace your inner-rock star with cool sunglasses. While cheap brands have a plethora of styles to choose from, a pair that's a little more expensive (but not too crazy), like Reese Witherspoon's Ray-Bans, won't break easily, and will protect your eyes because of the UV blocking lenses.
George likes: Ray-Ban sunglasses, $150
Trench Coat
A trench coat is the ultimate symbol of sophistication, which is why celebs tend to throw one on when they hit the streets. Buy a classic tailored wool-blend option—check out Michelle Dockery's Burberry stunner—and you'll have it forever!
George likes: Burberry Brit trench, $995
Little Black Dress
Fashionable chicks like Alexa Chung show up on the red carpet in little black dresses for a reason. They're effortless, foolproof and always on trend. Splurge on a classic style that's made of natural fabrics so it won't pill overtime.
George likes: Sandro dress, $250
Bold Clutch
A bold clutch in a vibrant color is an easy way to spice up a look—whether you want to pop up an LBD, or compliment an already vibrant frock like Kourtney Kardashian did here. Pick a classic shape made of luxurious leather, and you'll have in your closet forever.
George likes: Rebecca Minkoff clutch, $250
Black Tote
A fierce bag is one the easiest ways to elevate any ensemble. Take a cue from Ashley Olsen, who always has a fabulous bag on her arm. If you're looking to splurge on one, try a boxy black tote that pulls double duty. You'll be able to wear to the office with a power suit, or swung over your shoulder with your weekend duds. Just ensure you buy somethingsturdy enough so it won't get destroyed as you pile in your life.
George likes: Tila March tote, $885
Gray Blazer
Take note from Katherine McNamara and throw a grey blazer over your go-to jeans and tee combo to look instantly sophisticated and chic. Tip: Spend a little extra tailoring a wool option. A perfect fit makes anything look luxurious. Push the sleeves up for some instant chic.
George likes: Theory blazer, $395
White Button-Down
Think about a white button-down as your canvas. Either dress one up with a black skirt, tights and booties à la Freida Pinto. Or wear un-buttoned with a cool graphic tee and distressed jeans for a casual weekend look. Just note that a silk option (and a little bit of Spandex for comfort) won't bunch up at the buttons as much, and will last much longer than a regular cotton shirt.
George likes: Brooks Brothers Stretch Silk, $248
Ballet Flats
Classic flats are chicer than sneakers, and way more comfortable than sky-high heels. So essentially, the perfect go-to shoes—especially when they have comfy, well-made leather soles. Try them with skinny jeans and a cute top for a casual look like Cristina Ricci did here.
George likes: Repetto flats, $295
Leather Jacket
A leather bomber is one of the coolest items you can have in your closet. Throw one on over a sweater for day, or over a nighttime dress like Emilia Clarke did here to look downtown chic. Avoid faux-leather because it will look cheap and won't last overtime.
George likes: AllSaints jacket, $435
Classic Bracelet
A simple bangle is subtle, yet always chic. Wear one (or a few like Sofia Castro) with a sweatshirt and pair of skinnies on the weekend, or with a work-appropriate outfit for the office. Spending more on a classic piece made of real silver or gold ensures it will last, and won't warp or bend after a few wears.
George likes: Ariel Gordon bracelet, $360