The Budget Babe | Affordable Fashion & Style Blog

Ask BB: What to Wear on a First Date

I just recently started using an online dating site, and will be going on my first date. We'll be going out for coffee in the afternoon. I'm very nervous and have no clue what to wear to make a great first impression. I'm 23, and I live in Chicago. The weather here has been [warm] and sunny. —Caroline

When going on a first date, you want to be yourself, be comfortable and be approachable. Now is not the time to test drive new styles or trends that you wouldn't normally wear. You also don't want to come across as trying too hard - just be yourself!

Here are three outfit ideas that I think would work well for a first date at a coffee shop in the afternoon - opt for natural makeup and a good luck charm (for example, wear your favorite color, a meaningful pendant or a light spritz of your favorite perfume) for a little added boost of confidence.

Shown above: Rom-coms are always a good source of "date fashion" inspiration, as demonstrated here by Friends With Benefits co-stars Mila Kunis and Justin Timberlake.

(Click on any item for more details)

Look 1: You'll have to use your imagination to stitch these items together, but the gist of it is this: A pretty, feminine blouse, dark denim and ballet flats. Add your own jewelry for a personal touch. This look is cute, comfortable and gives off a warm, inviting vibe.

Look 2: I personally don't believe in showing too much skin on a first date (keep them coming back for more) but this striped top strikes a perfect balance of laid-back yet flirty with the little shoulder cut-outs. Fun jewelry can act as a welcome conversation starter.

Look 3: A casual cotton day dress or skirt is guaranteed to make a great first impression. Men love skirts, simple as that. Add a light layer that you can remove during the date if things are going well. Trust me, he'll notice.

What do you think makes a perfect first date outfit? Which of these three looks would you wear? What advice would you share with Caroline? xoBB

Keep it simple and wear something you're confident in! Nothing says sexy more than you feeling good in what you're wearing, and I live in Chicago so maybe a quick shopping trip soon?

xx, the B

Here's a first day outfit post I wrote a few months ago :-)
#1 The B (Homepage) on 2011-08-09 16:11 (Reply)
I think it is hard to pull off Look 2. It looks nice and easy, but with cuffed cropped pants and a casual knit top, it might look like I just get out of the gym.

Someone told me the rule is to combine 1 super flirty item with 1 casual item so that in combination you'll try the perfect balance.
#2 RomanceMath (Homepage) on 2011-08-09 16:58 (Reply)
Whatever you wear, be sure to wear cute shoes that are in good repair! There's nothing worse than ratty looking shoes. First impression is everything.

Case in point: my husband still remembers the pointy-toed black stilettos I wore on our first date (I wore them with jeans and a nice top).
#3 Jo from Canada (Homepage) on 2011-08-09 17:06 (Reply)
I really like look one. It can also be dressed up with a pair of heels although flats may be more appropriate for day time. I agree you shouldn't show too much skin. At the end of the day, it's dressing to your personality and comfort.
#4 Diana (Homepage) on 2011-08-09 17:11 (Reply)
#1 is the best imo! Very versatile and great for a coffee date, b/c you never know where it could go from there so you want to be prepared!
#5 MizzJ (Homepage) on 2011-08-09 18:56 (Reply)
Love all looks!! The dress is probably my favorite, love how flirty and classy it is.
#6 Nicole @ Giraffelegs (Homepage) on 2011-08-09 22:13 (Reply)
Don't wear anything fussy - it will only stress you out! I prefer tried and true pieces, items you know you look great in so you already feel confident. :-)
#7 Heather on 2011-08-10 00:16 (Reply)
I like #3 the best because dresses are more comfortable than jeans, in my opinion. You can really dig into your food if it's a date involving a meal, and not have your waistband get uncomfortable, etc. I've read that men get turned on by women who eat with gusto, or some such thing. Either way, it can't hurt!

Then again, the day I met my husband I wore a pair of J Brand skinny jeans and we were married less than a month later! :-)
#8 Anusha (Homepage) on 2011-08-10 02:43 (Reply)
Number 1 is my fav. Not too fussy, not too fancy yet cute and approachable!
#9 saretta (Homepage) on 2011-08-10 08:18 (Reply)
I would totally wear #3. But then again I am a dress kinda a gal. I love wearing dresses for a day or date nite out.
#10 Laura on 2011-08-10 09:50 (Reply)
i agree not to show too much skin, but guys do not like loose, billowy tops. they think you're "hiding something" so wear something a little more form-fitted. that same vibe as outfit #1 can be achieved with a fitted tshirt or tank and a blazer or cute cardigan. best accessory = a smile!
#11 vicki on 2011-08-10 10:43 (Reply)
I love outfit #2! That would get my pick.
#12 danielle on 2011-08-10 14:09 (Reply)
Outfit 1 for sure. I would and HAVE worn outfits just like that on first dates. Although, if you want to feel sexy, I'd wear a dress. Even if it's not a very revealing one, sometimes wearing something really feminine makes you feel more attractive.

It also really depends on where you are going on your date. Like, I'd feel stupid wearing a dress at a baseball game or something. I wouldn't want to wear heels to a coffee shop either. In that setting, it would really look like you're trying too hard (unless you just wear heels all the time).

Also, if these are dates from online dating sites, and you're not short, I would definitely not wear heels. What if he's super short? I find guys exaggerate height on dating sites a lot.

Good luck!
#13 Tracy Warner on 2011-08-11 11:37 (Reply)
Good point about removing the light jacket as you get more comfortable.

Outfit #3 is my favorite.

I would wear a dress. It's still summer!

I think it's ok to dress up a little bit.

I would wear a pretty summer dress (or skirt), and make it more casual by wearing a simple bag (maybe even a book bag) and open shoes (flats or wedges if you like heels). I like this dress for example:

(I saw it on sale at a free people store for $48 btw)

The nude pumps Mila Kunis is wearing look awesome. I need to see this movie :-).

I bought similar pumps at Payless. Unfortunately they look a little chunky because I got them half a size up to make up for the fact that the material felt pretty hard against my skin. Any tips on how to make hard shoes more comfortable?
#14 Deb (Homepage) on 2011-08-11 18:01 (Reply)
BB can you please do a mens look like Justin's?
#15 Vi on 2011-08-15 11:18 (Reply)
Hey BB,

I love the suggestions but could I ask you to be less heteronormative when making posts like these?
#16 S. on 2011-08-16 14:59 (Reply)
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