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Outfit Ideas Articles October 20, 2017

Can You Be Both Desirable and Comfortable on a First Date?

Your goal on a first date is to be desirable. You want to be sexy but not too sexy. Be flirty but not over the top flirty, where even the waiter asks for your phone number. You also want to have a dash of a little hard-to-get attitude. To produce this perfect blend on a first date, we’ve been taught that it requires tight clothing, sky-high heels, a barrel of perfume, and the removal of all body hair. These ingredients make it very hard to also feel comfortable on a first date. So your flirty ends up coming off as fidgety because you keep pulling at your Spanx all night.


You can wear comfortable clothes on a first date and still be sexy, flirty, and a little hard to get. Do you need comfortable outfit ideas for a date? I have you covered. Let’s start with a thermal shirt. It makes you think about camping, warmth, comfort, and outdoorsmen that prefer digging holes in the ground to toilets. It does not make you think “hot first date outfit,” but it can be. Wear a form-fitting thermal shirt that has buttons down the front of the neckline and pair this with boyfriend jeans, and wedges (not uncomfortable high heels).

The way you make the thermal shirt sexy and flirty is to unbutton a few of the buttons to have a hint of cleavage (by only fastening a few buttons and not all of them is how you achieve that hard-to-get appeal). There you go! Now, you have a cool, comfortable date outfit. Need more comfortable outfit ideas for a date, well…


We all love the comfort of leggings. To make them first date worthy, pair leggings with a slouchy off-the-shoulder top and boots. You are comfortable, you show off a sexy shoulder, and you get to wear boots on a date. Make this outfit even more flirty and feminine by properly accessorizing this look. You look great, and you have that effortless style look that makes other women crazy with jealousy.


If you like wearing a dress on a first date, here is a comfortable outfit idea for a date. You can wear a muumuu (yes, you read that correctly—a muumuu) and belt it. Wear it with gorgeous sandals or wedges (don’t forget your pedicure). Again, you have a look where you don’t have to worry about sucking in your stomach all night and being shaken away on the bathroom floor by the sous chef because you fainted from lack of oxygen. This is a first date dress that will allow you to breathe and even do those deep belly breathes your yoga instructor (or therapist or life coach) talks about.


Don’t believe what you see on The Bachelor. There are comfortable outfit ideas for a date that are sexy and flirty. You just need some imagination, some moral courage, and the ideas in this article. So don’t stress out. Just take a deep belly breath because you are comfortable in your own skin and in your clothes.

Style resources

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