Dressing for A Winter Date

Let’s face it: Boston dating can be challenging on all fronts, including weather! J Allen Matchmaking gets many questions from our clients about the different ways they can help make themselves feel comfortable on a first date, and one great place to start is with the outfit. Winter can make it difficult for women to decide on what’s appropriate, and we have a few suggestions!

Always lean towards comfort

We always talk about how important it is to feel comfortable in the clothes you are wearing, and winter is a great season to try a new style that makes you feel great! Layering clothes, wearing a darker lip or eye, or trying a new pair of booties can give you the confidence you have been looking for while still feeling yourself.

Know the environment

There is a big difference between a cozy date at a restaurant next to a fire and ice skating on Boston Commons. If and when possible, know the environment you will be in and dress accordingly. Being cold or sweating can cause a distraction from your date and leave you feeling uneasy.

Be practical

Though there is always an occasion for that little black dress, it might be best to leave it in the closet on the nights where the wind chill is -10. Always remember that though your date might be indoors, you should arrive at your destination without freezing to death! We live in a city where practical and functional clothes for the occasion are necessary, especially when the weather is always changing.

Though picking a great outfit is fantastic, J Allen Matchmaking knows that singles in Boston are looking for a much deeper connection. Our services help bring you together with potential matches who are fit for your lifestyle and personality. Janine cannot wait to meet you and learn about the kind of soulmate you are seeking.

If you have more questions about our services, contact us today at (617) 674-4458.

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