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If you're going to wear a prep school blazer like this one, all grey flannel with white trim and gold buttons, you have got to take it in a different direction from the country club dinner it wants to go in. Add a chambray shirt, untucked, with the shirttail sticking out, and white jeans or cords.

The other thing you have to do, is push up those sleeves so you don't look so stiff and buttoned up. Style Vault update: Shop a similar prep school blazer inside the October Style Vault, Style Notes.

I sometimes can dress in that "old lady vibe" way, too, if I'm not careful. If you have a fancy blazer, like this Chanel, wear it casually rather than all fancy. Toss it over your shoulders, the new, cool way women are wearing blazers in New York and Paris.

Chanel + TJ Maxx. Amy, one of our fab stylists, had this grey knit dress on at one of our team meetings and I had to have it. She got it at TJ Maxx so I hightailed it over there. And $14.99 later, I think it does pretty well by my Chanel. If you get cold, go ahead and put your arms through it. Style Vault update: I found you a great grey knit t-shirt dress for under $20 - inside the updated October Style Notes.

I want to go back to Switzerland. I spent a summer there once and it ruined me for any faux-Alpine experience forever. I need legit mountains with yodeling and snow peaks and fireplaces and furry accoutrements. A fox-trim blazer completes the fairytale.

Wear your tweedy, furry blazer with cozy sweaters and boots. Style Vault update: I put a blazer almost identical to this one in the September Style Vault (with a faux fur collar) and it was hugely popular. It's still available in most sizes! Shop now inside the September Vault. You can also shop this exact sweater ( I live in it) from the October Style Vault.

Hardly anyone has a great cocktail topper. Because no one is allowed to wear the matching little jacket that came with your evening gown unless it was made by someone named Oscar or Giorgio or Ralph or their friends. Most of them are awful. Soooo, you need a nice black blazer. Often called a tuxedo blazer. Satin or satin trim is what you need. It will go over cocktail dresses or pants, and even jeans when they need a bit fancying up. Yes, these shoes are square-toed, but see that little v at the toe cleavage? That keeps them from looking ugly and unflattering. Style Vault update: Shop 2  beautiful black cocktail blazers inside the updated October Style Vault.

A winter white tuxedo blazer can also be a great cocktail topper. I'm wearing mine (I have 3 winter white blazers, surprise, surprise) with a beaded skirt and dressy accessories.

This one is trimmed in satin, but winter white will appear dressy even if it doesn't have that trim, and it will be beautiful against all your jewel tones, bright colors, and with neutrals. Style Vault update: Shop 2 gorgeous winter white blazers inside the updated October Style Vault, in Style Notes.