White Silk Button Down: One of my first "investment pieces" was buying this Truve silk blouse. It classic color, style, and shape allows me to pair it with virtually anything. You can dress it down with jeans, throw it over a fitted dress or skirt and belt it, if you like, or tuck it in to a pencil skirt with a cool print or fabric.
Vintage Denim Shorts: I got these shorts at my favorite vintage store during my first summer in NYC, but you can find vintage jeans virtually anywhere.... namely Goodwill. You might have to try on a million pairs, but once you find the right pair, it's like pulling on fuzzy socks on a cold day. Experiment with different shapes, washes, and lengths to find you favorites.
Leather Wedges: I got these Dolce Vita the same summer as my denim shorts, and needless to say, they are my favorite and most comfortable pair of wedges. Invest in a pair in a neutral color with good leather that will last. It's worth it to spend a bit more on styles that will LAST the wear and tear of all that comes with life :)
Ladylike Purse: While the ladylike purse has been the rage this season, it is a classic that will never stop being in vogue. I scored this white leather crossbody with gold detail in a garage sale for $3. If you can't afford what's out in stores now, search your latest garage sale or thrift store. You never know what you will find.