What should frumpy happily married mom wear to wear to dinner with old boyfriend?

[Anonymous]

I'm slowly rebuilding my wardrobe after finally losing 2 babies' worth of weight and buying no decent non-maternity clothes in 3 years. I'm a size 10, maybe an 8 with Spanx. I've got big boobs, a bit of a belly but smallish hips and OK legs. My current go-to weekend outfit is leggings/jeggings with a long top or sweater and frye boots. To work I wear boring black/gray pants and sweaters or the occasional wrap dress. Sad to say I haven't needed anything more fun that that in quite a while. I almost never accessorize beyond my wedding rings and everyday (nice) watch.

In a few weeks my college boyfriend will be in town for work and we are meeting up for dinner/drinks. It's been over 10 years since I've seen him, although we've always emailed once or twice a year. (We are both happily married with families and my DH knows there's truly nothing shady about us meeting up.) I'm definitel not trying to "attract" him, but at the same time I'd still rather not look like the frumpy wrinkled harridan in mom pants I guess I've become.


I'm willing to buy a new outfit for this because once I have it I'm sure I will wear it again. Suggestions, please?? Be as specific as possible--shoes, accessories, where to shop, even links would be awesome.

I'd love to wear my Frye boots with whatever it is but I wonder if they are too casual? They are a nice riding style, not too chunky or heavy looking.

Thanks so much for any help!!!

[Anonymous]

Your clothes sound fine. I would get a good haircut, manicure, and earrings.

[Anonymous]

I just bought this dress. It would probably look great on you. Wear it with nice black heels, nice earrings, doesn't really call for a necklace. Get your hair blown out the day and don't wash it. Make sure you wear all your makeup. Do the 15 minute face, not the 5 minute one.
http://shop.nordstrom.com/s/kenneth-cole-new-york-twist-waist-dress/3147613?origin=category&resultback=370

[Anonymous]

Anonymous wrote:I'm slowly rebuilding my wardrobe after finally losing 2 babies' worth of weight and buying no decent non-maternity clothes in 3 years. I'm a size 10, maybe an 8 with Spanx. I've got big boobs, a bit of a belly but smallish hips and OK legs. My current go-to weekend outfit is leggings/jeggings with a long top or sweater and frye boots. To work I wear boring black/gray pants and sweaters or the occasional wrap dress. Sad to say I haven't needed anything more fun that that in quite a while. I almost never accessorize beyond my wedding rings and everyday (nice) watch.

In a few weeks my college boyfriend will be in town for work and we are meeting up for dinner/drinks. It's been over 10 years since I've seen him, although we've always emailed once or twice a year. (We are both happily married with families and my DH knows there's truly nothing shady about us meeting up.) I'm definitel not trying to "attract" him, but at the same time I'd still rather not look like the frumpy wrinkled harridan in mom pants I guess I've become.


I'm willing to buy a new outfit for this because once I have it I'm sure I will wear it again. Suggestions, please?? Be as specific as possible--shoes, accessories, where to shop, even links would be awesome.

I'd love to wear my Frye boots with whatever it is but I wonder if they are too casual? They are a nice riding style, not too chunky or heavy looking.

Thanks so much for any help!!!

How fancy a place are you talking about?

[Anonymous]

Really? A ZEBRA DRESS??? That dress would be great, in a solid color.

[Anonymous]

My style would be:
1. Flattering haircut and style.
2. Elaborate but natural-looking make-up. Check it under the same lighting conditions that you will have on the night.
3. With your body type, I would do a short dress to show your legs, but an empire waist to hide the belly. No cleavage!
4. Heels, if you can walk in them.

5. And don't agonize and prep for hours about this in front of DH, because even mellow men have their limit!

[Anonymous]

OMG. I want to go to dinner with my old boyfriend too!!!

[Anonymous]

Sounds like fun! I second the advice already given. One more thing - get as much good sleep as you can every night for the week prior. I look years younger when I get decent sleep. Doesn't happen very often, unfortunately.

[Anonymous]

Anonymous wrote:My style would be:
1. Flattering haircut and style.
2. Elaborate but natural-looking make-up. Check it under the same lighting conditions that you will have on the night.
3. With your body type, I would do a short dress to show your legs, but an empire waist to hide the belly. No cleavage!
4. Heels, if you can walk in them.

5. And don't agonize and prep for hours about this in front of DH, because even mellow men have their limit!

No, no, no! Have you seen anyone over the age of 9 look good in an empire-waist dress?

Go for a dress that has some ruching or gathering on the side--like a Diane Von Furstenberg wrap dress.

Also, no short dresses--something that hits above the knee is OK, but not too short.

You want to look classy sexy, not young and hoochy.

[Anonymous]

17:18 coming back. Yes PP! Sleep and lots of water during that week.

[Anonymous]

I think you should wear dark jeans/jeggings, your Frye boots, and a snazzy top with a smart looking jacket or cardigan. For inspiration, think British effortless. At least that is what I am thinking. I know this isn't shady, but you still don't want to look like you tried too hard. Plus, you want to be comfortable.

As for where to buy tops, depends on what flatters you and where you like to shop. Anthro, BR, JCrew, Nordstroms.

Oh, and congratulations on losing the weight! How'd you do it?

[Anonymous]

Anonymous wrote:I think you should wear dark jeans/jeggings, your Frye boots, and a snazzy top with a smart looking jacket or cardigan. For inspiration, think British effortless. At least that is what I am thinking. I know this isn't shady, but you still don't want to look like you tried too hard. Plus, you want to be comfortable.

As for where to buy tops, depends on what flatters you and where you like to shop. Anthro, BR, JCrew, Nordstroms.

Oh, and congratulations on losing the weight! How'd you do it?

Agree with this poster (and the sleep advice). Save the zebra dress for a surprise date night with your husband.

[Anonymous]

I agree with all the sleep/water/good haircut and make up advice I would get good, flattering (tailored to fit you) dark jeans to wear with your frye boots - if you like the ones you have, great. Then i would wear the jeans and boots to nordstrom's and have a salesperson help you - tell her you want a top to go with the jeans and boots that is good for evening/cocktails.

[Anonymous]

OP here--this is great. 17:42 you are so right about # 5!

[Anonymous]

Whoops I meant 17:18