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Ask Leslie

What is an appropriate outfit to wear for an office holiday party? Is a short dress or skirt too inappropriate if you’re the youngest at the office? 

Dear Youngest at the Office,

How thoughtful of you to consider the vibe before the outfit. Here’s the thing: if you have to ask yourself whether it’s too short, it probably is. Go festive, not flirty. You want your outfit to spark compliments, not a group chat you’re left out of the next morning.

Here are some of my go-to polished brands: 

-Veronica Beard (Greenwich)

-Reiss (Norwalk Bloomingdales)

-Ralph Lauren (New Canaan)

Classy always reads confidence, and that never goes out of style, young one. 

-Leslie

What is the best way to keep romance going when everyday life gets in the way?

Dear Romance, 

Keeping the spark alive while juggling everything life throws at you isn’t easy, but it’s not impossible either. You just have to plan for it like you would anything else that matters, like doctor’s appointments, Amazon returns, or wine deliveries.

Saying you’ll do date night is cute, but let’s be real, something always comes up. So commit to anything that gets you two alone: maybe a long lunch, a spontaneous after-work drink, or a night out that involves real clothes and zero distractions. Bonus tip: buy tickets. To a concert, comedy show, whatever. When money’s on the line, romance magically makes the calendar.

And one last bonus tip: wear something new, whether it’s over or under your clothing. It’ll make you feel sexy, and your partner wishing the night would never end.

Here are some of my favorite date night spots lately:

-Capitol Theatre (Port Chester) - dine at Felice before the show! 

-The Granola Bar (Darien)

-Sole (New Canaan)

-Bedford Post Inn (Bedford, NY)

The best love stories don’t age, they just keep rewriting themselves.

-Leslie

What would be some inventive hostess gifts for someone that hosts you regularly? Assuming you have already exhausted all the standards. Thanks!

Dear Repeat Visitor,

Oh, you’re speaking my love language! I adore a good hostess gift, it’s such a timeless gesture that never goes unnoticed.

If you’ve already exhausted the usual suspects (gourmet treats, flowers, wine), it’s time to get a little creative. Channel your inner detective: listen for clues. Did she just mention an upcoming trip to Europe? Picking up tennis again? Trying meditation? That’s your intel. Follow the trail.

Here are a few of my go-to shops for hostess gifts: 

-Terrain (Westport)

-She La La (New Canaan)

-Darien Sport Shop (Darien)

The best gifts say, “I was paying attention.” A little intention goes a long way, and your host will feel both seen and spoiled.

-Leslie

In a world focused on connection and networking, how should you handle a friend who intentionally excludes you from activities to control her inner circle and prevent close friendships from developing? What strategies or steps would you recommend in this situation?

Dear Over It,

I’m so sorry you’re dealing with this. That kind of exclusion stings. But let’s be clear: a “friend” who intentionally shuts you out to control her circle isn’t a friend at all. That’s not connection, that’s insecurity.

It sounds like she’s threatened by you, maybe worried her besties will become your besties. You don’t need her permission to build real friendships.

Here's my advice: cut out the middlewoman. If you genuinely like the other women, reach out directly. Invite one for coffee, a walk, or cocktails. See where it goes. You might be surprised how many of them have noticed her behavior too.

Here are a few of my favorite spots for some girly time:

-Waveny Park for a walk (New Canaan)

-Cafe Nero for coffee (Darien)

-The Waveny Bar & Grill or Molto for cocktails (New Canaan & Darien)

Bottom line: take the detour. The real power move isn’t getting invited, it’s realizing you don’t need the invitation.

-Leslie

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