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If you want a more pourable dressing, add buttermilk by the tablespoon until it is thin enough for you.

In warmer weather for a wedding you can wear heeled sandals in a contrasting color

Black loafers and black boots work very nicely with dark jeans, and I wear this extensively when going out in the evening

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If your office is conservative but not formal enough to require you to wear a two-piece suit daily, then a button-down shirt and tie with dress shoes is a safe outfit for men