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Ask Val: “Dating in Denim”


“What can I wear to feel sexy on a date?” — Melissa G. (Miami, FL)


Well, Miss Melissa…I could easily answer this question with suggestions like “Cleavage” (too risky, keep it more demure if it’s a first date) or “Red Lips” (I’ve found that men usually do not prefer this look, plus it’s messy and requires re-applying often!) or even “A Little Black Dress” (Boring. Too predictable!) So I’ll recommend something you may have overlooked….


Anyone that knows me will be SHOCKED that I even uttered that word. (I do wear jeans on occasion but I am not the biggest fan.) The reason you are going on this date though (I hope) is that you like this dude enough to value his opinion of what you look like. Men….LOVE jeans on a woman. I think it evokes a certain “girl next door” feel. A girl in jeans doesn’t take herself too seriously. Call it the “UN-intimidation factor”.

However! (And here is where Classic Val gets on her soapbox….) The casual feel of jeans should always be juxtaposed with fancier pieces. Envision yourself in slim jeans (or even a slouchier, ripped up boyfriend style) topped off with a pretty white tank and a structured blazer. Either in basic black (very classy!) or a fun, bold color that flatters your skintone. 

With accessories I would choose a long, tasseled chain necklace or a shorter sparkly bib necklace. If the rest of your outfit is pretty basic you can have fun with choosing a bag in a print or metallic finish. I do implore you to try a clutch, though! It just feels more “date-y” to carry something smaller than your everyday handbag. You know which one I mean. The one that’s so ridiculously big that the bottom is lined with 3 year old altoid mints. (We ALL have that bag…)

Heels are a must but keep in mind you want this guy to see the real you. The fun you! Not the “I’m insanely tall in these shoes and I’m walking funny because they kill my feet…” version of you. 

Finally, for makeup I’d do a smoky gray or brown eye (black may be too severe) and keep your blush and lipstick/lipgloss more natural. I would suggest leaving your hair down, loose & tousled or however you normally wear your hair. This is NOT the time to experiment with a hairdo you aren’t used to maintaining. You want to be comfortable!

Have fun, girl! And only kiss him if he’s worth it…   😉



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