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What makes The Oak Bar a standout, and one of Boston’s best hotspots for 40-somethings, is the live entertainment Wednesday through Saturday nights.

The large martini menu and extensive raw bar aren’t too shabby either.

Guys need to learn that having witty reparte will get them nowhere if their everyday wardrobes don't include a good dose of cool, casual style.

More Articles for Baby Boomer Men and Women: It's Hip to be Old: Things They Should Make for Baby Boomers Cute Hearing Aids for Rock & Roll Boomer Chicks Best Cruiser Bikes for Older Women: Seniors & Baby Boomers How to Save Money on RV Camping Fees What do you think of this article?

When it’s cold out, you can wear a long leather jacket or a windbreaker or anything you can button or zip to hide your stomach. What I am getting at specifically, is your white jogging-tennis shoes. I understand that most guys are hopeless when it comes to fashion, but I don’t think I’m asking too much of you.

Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world.

When it’s warm, but not warm enough for a full-on jacket, the best overshirt is a denim shirt. It’s not my fault that you didn’t break your shoes in properly. Well, not like German tourists, but I know that asking you to dress like Londoners would be asking too much...

You can roll up the sleeves if you want to be cool. If you guys absolutely must wear shorts, please wear deck shoes or loafers or sandals without any freaking socks of any kind. if you grew up thinking that Europe and Epcot are somehow related. Just don’t wear socks with shorts (unless you know what you’re doing) or ugly white Nikes with any activity that doesn’t involve hoops, bats, gloves, helmets, rackets, or wickets.

Lenox Hotel 61 Exeter Street at Boylston Boston, MA 02116 (617) 933-4800 Bar might be small in size, but the intimate setting is what makes this bar one of Boston’s best hotspots for 40-somethings.

Dimly lit with comfortable seating, City Bar makes you want to get cozy while sipping a sophisticated cocktail.

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