Fashion & Beauty

Dressing Tips for a First Date at 40

Dating is a tricky game in your 40’s. It’s how you carry yourself, the stories you tell, the food you order, the way you speak, basic mannerisms and even how many toilet breaks you take. Everything is going to be put under a microscope –especially if it’s a first date, and even more so if you’re just recently jumping back on the dating bandwagon. Although personality traits will boil down to each unique individual, what we can help you with is how to make a killer first impression!

It can be nerve wrecking to venture out into the dating shark pool as a woman in your 40s. Although at this age men and women generally know what they want in a potential partner, there is still all that awkward ice breaking and small talk you have to persevere through before the conversations get a little more meaningful and deep.

Before agreeing to go out with your potential McDreamy, you should think about an optimal location that would benefit your first date. If you can hold your liquor and need some alcohol confidence –maybe some drinks at your local bar? Or if you plan on glamming up for a fancy dinner date with food on the menu that you can indeed pronounce, that would be a great choice too! However for the most part, first dates are usually a casual occasion.


The problematic thing about casual dates, is that you don’t want to look like you’re trying too hard but at the same time want to look impressionable. The solution would be to wear something you can never go wrong in –jeans! Jeans come in many various cuts and sizes, so you should choose something that you feel great in and also compliments your body shape. Although I might suggest staying away from the overly baggy jeans (no matter how comfortable you think they are).


Cheeky Top

Now start raiding your closet for all the tops you know you look good in. It’s only the first date, so you may not want to go on to the extremes like glitter, sequins or too much boobage but a little skin wouldn’t hurt. If you’re really planning on playing it casual, a basic coloured tank top would do the trick. It’s simple, classy, and would definitely get a few head turns. However, if you’re feeling a little feisty and want to amp it up a little, maybe throw in a lacy number or even plain jumper with a little plunging neckline. My personal advice is to avoid black clothing, as bars are normally dimly lit and an opposing colour would surely earn you a little extra attention you deserve.


I cannot stress how important your outerwear is as it sets the theme of your entire outfit. Depending on what kind of vibe you want to portray may it be flirty, sexy, dominant, outgoing or even sporty there is definitely a different outwear variation for each kind. If you’re planning on looking a little flirty, maybe a floral print kimono, a leather jacket for a sultry sexy look or you can throw on a contrasting coloured cardigan for a more chique outgoing appearance.

Hair & Make Up

As I’ve mentioned previously, you don’t want to seem like you’re trying to hard especially when it comes to make up. Cakey over applied make up on your first outing together may look a little desperate, especially if it’s a casual date. Ideally for makeup you would want to use the basics – some primer, foundation, a little eyeliner, a nude shade of lipstick and a few coats of mascara if you’re feeling bold. Hair wise, setting in some beachy wavy curls would definitely paint a pretty picture.


As said in famous Korean drama Boys Over Flowers, “good shoes take you to good places”. Men definitely notice when you wear a stunning pair of shoes as it is the statement piece to your entire fashion ensemble. If you have a pair of black booties, or some suede pointed heels (that you feel comfortable enough to walk out in) it would definitely make a lasting first impression. If by chance you’d rather not make a fool of yourself in heels, you could select some pretty flats preferably a closed toe option.

For The Not So Casual Dates

If by chance you’re jumping straight to the fancy sophisticated dinner on the first date, be prepared to bring your A-Game. If it’s fancy dinner we’re talking, you’re allowed to be a little extra. Blow some dust off that fancy dress in your closet you’ve been saving for a special occasion, maybe a mid-length sleeveless dress. For you ladies with a tiny waist, you can choose an A-Line cut dress or just wear a high waisted skirt paired with a matching top. In terms of hair and makeup, the bolder the better. Wear that dark red lipstick, and maybe feather on a smokey eye shadow for a sexy finish. Blow out your hair, do your nails, bring out the pumps, get that stunning black coat, but most importantly make sure you feel amazing and confident when stepping out your front door. At the end of the day, the dating scene can be brutal especially if you’re new to it. However as long as you’re attracted to the person, have a good connection and get along on the same wavelength, you wouldn’t need fancy shoes or a plunging neckline to gain the right attention.

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