Here are some really varied combinations of boots and bottoms so you can find a set that fits your personal style.

1. Look 1 from Forever 21 combines the trendy and the retro. Can you guess which is which? Although the dress is from Forever 21, it has cute, 50’s styling. Ankle boots, which were popular in the 80’s, have made a huge comeback. To spice up the look: Add a scarf, headband and black or colored tights. For something more edgy, wear leggings with the dress.
2. Look 2 from Delias is for the daring fashionista. When I saw these boots, my eyes nearly popped out of my head. Pink! And plaid! And a button! These boots include so many fashion trends in one small package that it’s hard to figure how to pair them. The best way to make these boots be the stand-out item is to pair them with other solid colored clothing. These black skinny jeans, for example, let the boots stand on their own. To spice up the look: Wear the boots with a contrasting solid color up top. Bright blue, maybe?
3. Look 3 from Urban Outfitters is all me. I like wearing muted patterns and colors–nothing too wild!–and pairing them with interesting footwear and accessories. These boots are versatile and stylish, and I can’t say enough good things about this Urban Outfitters shirt dress. To spice up the look: Add a bright-colored jacket (yellow, orange, etc.), throw on some gray tights and put on a chunky necklace.
4. Look 4 from Target is the epitome of ladylike-chic dressing. This dress is fantastic–I love winter white. The boots, though, are the real catch. Less than $35 from Target, and they look hot. I love the mini wedge. Perfect for winter, perfect with a dress like this. Add some tights or leggings if you get cold. To spice up the look: Throw on some big sunglasses and belt that dress!
5. Look 5 from Alloy is trendy, trendy, trendy. From the colored pants to the low-heeled boots, there is nothing subtle going on here. Step out in confidence–after all, colored pants are all over the place right now and be amazed as the compliments roll in. To spice up the look: Wear something patterned on top. A houndstooth scarf with a simple, chic peacoat would lend a mod edge here.

Here’s what to look for when you shop for a retro glam or collegiate charm look:

1. The print of this gingham dress is new and trendy, but the old-school 50’s cut is all vintage-chic. To dress retro glam, don’t be afraid to wear vintage cuts in new and unexpected ways. If a print is a little too old-fashioned for you, have the dress, skirt or blouse altered into a more modern shape. On the other hand, if the cut of the item is very vintage, pair it with modern accessories to avoid a costumed appearance.
2. Jewelry is key to a retro glam look. A little goes a long way, and try mix up what you wear so as not to appear straight out of Grease, for example. Pearls would be too much with this outfit, so I paired the retro-fitting dress with a long, rock-and-roll chain necklace.
3. When it comes to retro glam, the bigger the sunglasses, the better.
4. Much to my eternal dismay, the shoes pictured above are no longer available on the fickle friend that is Forever 21 online. However, try these alternatives. Here’s what to look for: a chunkier heel (no stilettos), buckles, round-toes, vintage (gold, red, etc.) or muted colors, mary-jane styles or classic peep-toe pumps.
5. A scarf completes the retro glam outfit. Tie it loosely, or with a more retro-flair by flipping one end over your shoulder.
6. For a bit of authentic ladylike coordination, use a clutch instead of your huge, leather tote.
7. A 50’s/60’s style jacket finishes off the outfit. A bit of boxiness is a must. Look for large buttons or a peter pan collar. With longer dresses/skirts, try a cropped jacket. If you’re wearing something shorter on the bottom, then make sure your coat falls slightly above your hemline, but not too far.

1. Start off with an interesting blouse. It can be longer, like a tunic, or a bit shorter. Ruffles are preferred, but not required. A print is good also, but a solid color is easier to coordinate the accessories with.
2. Every collegiate girl worth her salt knows that some plastic-framed reading glasses add a bit of quirky charm.
3. A few bright-colored items in a coordinating color family add some conversation pieces to the entire outfit. See how well the colored pants, bracelet and blue cardigan look together? The yellow on this bracelet is a bright color, yes, but is also surprisingly neutral.
4. A long, grandpa-style cardigan worn over the blouse helps keep you warm, but that’s not the real reason I included it. Skinny jeans are tricky to proportion: if your top is too short, you end up looking very “hippy,” or bottom-heavy, without balance on your upper-half. Use a longer cardigan to correct that and balance out your collegiate charm look.
5. A big, leather tote bag serves two purposes: one, it has that collegiate–and somewhat scholarly–look we are aiming towards without seeming like a briefcase. And the second reason is that the bag adds a good neutral base for the entire outfit.
6. Interesting, comfortable shoes with a slight heel to accentuate the skinny pants: these are exactly what I’m talking about.
7. An outfit with a bit of quirk would not be complete without a standout piece of jewelry, like this snake bracelet.
8. Skinny pants with color, instead of the classic denim washes, are fun and easier to wear than you might think.

Do you have more Retro Glam or Collegiate Charm?