what to wear

[imissdow]

I had date #2 last night and we started planning date #3  Went to a really nice Italian place spent 3 1/2 hours talking, laughing and eating dinner.  Looked in my closet for a outfit and realized I have 1 pair of dress slacks and all my dresses are about 15 years old I think the last time I actually wore a dress was 6 years ago. I finally threw out the heels I used to have as they were cracked and ruined I think I actually wore them 5 times. So I ended up wearing the same slacks and shoes I wore the last date and found a different shirt to wear.  I seriously need to go shopping but I'm not sure exactly what to buy.  I know I don't want a ton of new clothes I will only wear once or twice So I'm thinking black slacks a couple of shirts and maybe a sweater.  I have tons of jeans, tee's, tanks hoodies and a few sweaters.  I have dated a few times in the past couple of years but with the exception of one guy no one has ever gotten past date 2.  This guy picks nicer places then I usually frequent.  I usually have 3 kids along and none of these places even have a kids menu.  I really don't want dresses however I would like stuff that can be dressy or casual.  I don't want leggings or yoga pants.  So what do I buy?   

[Captains wife]

Date clothes...that can be a tough one. If you want repeat wear, I would get the following - you can dress these up or down. 1)1) Nice pair of very dark jeans - skinny jeans if you feel comfortable wearing that fit. You can buy a few pretty, bright coloured tunic type tops to wear with them, or blouses. 2) 2-3 pairs of trousers that are neutral in color - i.e. black, tan. You can buy a pair that is between dressy and casual at a place like Ann Taylor or Loft. I like the straight leg ones but boot leg can be very flattering for certain figures. 3) Treat yourself to a couple of dressier blouses/shirts - I, for example, love the crossover type shirt - in jersey type material. Buy in basic colours (black, dark grey, blue) and then you can dress that up with a nice necklace (i.e. can buy very pretty inexpensive costume jewelry). I also own a few tops that are more blouse-like (ie made of silk or even polyester) that "drape" and I will wear with casual trousers. Will dress this up with a necklace and clutch (again, can be very inexpensive), 4) I personally like having a few basic dresses in my wardrobe and you can buy cotton/jersey wrap around dresses that are slightly more casual and are flattering.

 

You can wear flats OR heels OR boots with any of these outfits.

[Guest Bear1956]

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[Portside]

Shoot, most fellas wouldn't notice if you wore the same outfit three times in a row.

 

We're like that you know.  ;D

 

Mike

[Mangomom]

Let me preface by stating that I have not been on a "date" in 20 years...

 

I am not a dressy kind of girl.  I will wear a dress or slacks to church occasionally, but I am a jeans and sweater girl.  Don't create a persona that you aren't comfortable with, wearing clothes that are out of your zone.

 

My favorite "dressy" clothes are a pair of tailored jeans - Ann Taylor style, no pockets, worn with heels - and a blouse or shell that I can layer a sweater over.  J Jill has some great versatile pieces, like a great stretchy black skirt that you can dress up or down.  Scarves do wonders for a plain white t-shirt (or simple colored shirt).  Shoes go a long way, too.  I love my BOC's, but not when I am dressing up.  Unless it is a ridiculously upscale establishment, I think that "no jeans" would be the only rule to apply.  Call me simple   AND!!!  Make sure it is all washable!  I hate the dry cleaning bills!

 

As a side note:  make sure he also takes you to "your type" of places as well.  I love a fancy dinner, but I am a huge fan of casual, fun, don't stress about the 20 forks places.

[Trying]

I agree with Mangomom, stick with what you are comfortable in.  A dark wash pair of jeans can be dressed up with heals or boots and a nice top, anything that makes you feel good about you.  He will notice you being comfortable and confident more than anything.  A new pair of jeans and a pair of black slacks that fit well go a long way.

 

Most importantly, have fun on date # 3!

[calimom]

Cool jeans and a suede jacket with a nice top - don't be afraid to show off "the girls" a little bit.  Boots or sandals, depending on your weather.

 

Long halter style dress.  Lots of great stuff at even Target these days for not a lot of $$.

 

I agree with the above poster who said every date does not have to be an event restaurant.  Mexican food and margaritas can be fun too!  And going into the nicer weather, concerts in the park and that kind of thing works too.

 

 

[swilson]

I'm no where near ready to even think about dating, but it impresses me that y'all are enjoying each others company for 3-1/2 hours. Hope you have a great # 3.

[Sugarbell]

Shoot, most fellas wouldn't notice if you wore the same outfit three times in a row.

 

We're like that you know.  ;D

 

Mike

 

Yup. They don't notice.

 

I tend to err on the conservative side for the first few dates...(but not blah boring...I just want them to see me not the outfit..once I am comfortable with a guy I let loose more-but that's my hang up)

 

Your tall like me...I have found investing in quality more expensive pants...I get years of use out of them and they are versatile. Black, gray, taupe and casual off white in summer...I can switch around with different tops (I order the long sizes..I love LEL catalog and JCrew)

 

Summer....skorts are great. You can make them casual or dressy..Very versatile. I only own 2...but have like 15 different looks from them.

 

One black pencil skirt above knee for work. One tall sized maxi dress (Ann Taylor)

 

Just be comfortable most important! Your confidence shows through when you are comfortable-and he's going to be focused on your attitude, smile, mannerisms, conversation much more than your outfit.

 

Oh and I did wear yoga pants on date two with new friend. Long sweaters with dark yoga pants make your legs look even longer!

[Gabzmom]

Everyone has suggested great options.  I like scarves and tend to throw one on with a dress as a wrap, or knotted with a pair of slacks or jeans.  I am a shoe freak and the shoes/heels/boots seem to dress up the jeans. 

 

Have fun!

[Guest look2thesky]

Well I for one, notice. I go to Kohls for the sales. So what it's clearance. I wear them 10 times and then donate. It keeps the economy going ; )

[imissdow]

Some great Ideas.  I actually have several pairs of dark wash jeans and they are even fairly new.  I went shopping today and came home with nothing.  I guess I will need to order some slacks as no one carries any that are long enough for heels no matter how low they are. Thanks for telling me about LEL sugarbell ,I didn't know about them.  I also want to look for some skorts I used to wear them all the time not sure why I quit.

My friend owns his own business and does pig roasts on the weekends. So far this is working well for me because most of my DD's stuff is on the weekends so I don't need to pick and choose or try to decide if I'm comfortable inviting him yet. So we end up going out on a weeknight. Lets just say the pickings are slim as far as entertainment during the week.  I suggested a BBQ place for next time so jeans are perfect and more of the type of place my girls and I would go. I really don't think I need to worry about projecting a image with this guy we having been chatting face to face for almost 10 months. He has seen most of my wardrobe already and it didn't seem to bother him at all.