The Skinny Black Pant: You can dress it up or down and pair it with virtually any shoes. For Fall and Winter, I like to look for a slightly longer inseam (at least 28" for the average person, and I prefer at least 31" because I'm 5'8") so I don't have cold ankles.
The Denim Jacket: you can wear it with anything.
The Basic Sweatshirt: This item is a mandatory layering piece. You can toss it on solo with some skinnies and flats, or bundle up with a button down underneath and a utility jacket on top. Plus it's cozy, and lower maintenance than sweaters. Lower maintenance = Win. (I am the LAZIEST launderer ever. If it requires ironing/dry cleaning/etc I will pretty much wear it until it's dirty and then consider cleaning it six months later....)
The Utility Jacket: See 'Denim Jacket'. Really though, as far as casual versatility goes, nothing trumps a utility jacket. Olive is classic, but navy, beige, or any other neutral is just as handy to have at your disposal. If you have a shopping problem like me, then consider investing in a more obscure color too, like pale pink.
The Straight Leg Jean: You know that perfect sloppy jean cuff you're seeing in all the magazines? The secret is straight leg jeans. Cuffed straight leg jeans with ankle boots is a super cute look, plus straight legs are universally flattering.
The Chambray Button Down: I have more than 10 and wear one at least 3 times a week. They layer with everything from t-shirts to sequins, and don't need to be ironed. I'd recommend a lighter-medium colored shade if you're purchasing your first. Since dark denim is more prevalent right now, that'll decrease your chances of matching your top and bottom... because that can look a little silly (unless you're a J.Crew model...)
The Plaid Shirt: Pretty much the same logic as the chambray button down.
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