LL Bean does have a classic look, but their cuts can be a little dowdy IMHO and, to me, I think of them as the land of kids' school uniforms. (ETA; omg, I am thinking of Lands End! Whatevs, they seem similar to me. ) At a similar price point, I might look at J. Crew.

Classic Hamptons? I think really well tailored button down linen or cotton shirts in white or light blue, and nice fitting tailored capris in khaki or white, with fun flip flops (Tory Burch has cute ones ... there is another cool brand too, have to look it up) and nice big summery bag, straw (Mar y sol , iirc) or canvas. Get the shirt sleeveless or roll them up.

Or, you can go blingy and channel Pulitzer.

Get a pedicure, haircut, brows, etc before you go. You need to perfectly groomed to stand up to hot weather.

ETA: Basically you want to look like you are about to go riding or sailing. : )

Watch some reruns of Real Housewives Of New York. They were always hanging out in the Hamptons. Anything Lilly.

Look here for ideas, too.

I was trying to remember this brand, but one of DD just bought a pr of these over the w/e; they are so cute!

get a bunch!

You would think after 20+ years of going there, I would have it down, right? :-) It's just not my normal lifestyle. I wear nice work clothes, and then I'm completely casual, verging on grubby, at home. I have a real lack of nice casual clothes.

I'm 43, 5'4", apple shape, heavy, pale, redhead. I melt in the humidity. Not a beach babe! Not a Real Housewife! Thus my problem.

Classic preppy/Lilly Pulitzer/LL Bean is just not my style. I prefer darker colors, no wild patterns, simple cuts, not fussy or trendy, maybe a little boho/aging hippie left over from my younger years. I do love nice jewelry, handbags, and shoes.

I have one SIL who is very cutting edge, wild trends, skimpy clothes; one SIL who is a professional shopper at JCrew; one who lives in South Beach (Miami) and dresses that way; and one who is very traditional New England preppy style. DH's parents are very traditional and low-key, linen & khakis, etc.

Love Tory Burch, but my budget is state employee in a bleeding heart job, ie poverty. I just passed my twenty years of service mark, and my gift from the state was..... $200! LOL!

Ok, so this turned into a rambling post with no real solutions. I'll just be who I am, and wear what I'm comfortable in, as usual! Looking forward to unscheduled days of beach, naps, drinks, etc!

Thanks for the ideas, everyone. Mtn, those flip flops are perfect, I'm going to order some! Appreciate your other ideas as well. My various grooming appointments are all scheduled.

It's vacation-- so wearing a style that you are comfortable in is key-- both physically and mentally. I think linen shirts and tunics like roarah and Mtn suggested would work with your shape and slightly boho hippie style. The best part is that this style can move pretty easily from beach to backyard to shopping village to dinner (within some limits) by changing shoes and jewelry!

If you are looking to pick up a piece or two, there are a lot of summer sales going on now. I bought the top below for my mother last year and she's been wearing the heck out of it-- she is also very sensitive to the humidity and she loves that it keeps her cool without making her feel exposed-- and it's so easy. She throws it on over a tank and adds a large pendant and it looks great. It's Jjill and they also have some nice loose linen button down shirts and other light summer weight tunics and shirts. All on sale.

Whatever you wear--- you'll feel great with a fresh mani/pedi and a smile! Enjoy!

I second Funkyart's suggestion to look at Jjill. And yes, pencil stuff isn't going to really work for you anyway. You're on vacation. Be comfortable! Be who you are and wear what you are most comfortable in. That is always a person's best look anyway.

I would head to a large, good department store and try on all kinds of things you do not normally wear. It's a little late to be buying summer items, but you should be able to find some sale items. Do not buy the items with the idea you will wear them at your home, these are for vacation.
Or head to a boutique, they're not all for young skinny fashionistas.

Just don't give up! Put some effort into it and you will be rewarded by feeling great when you have the right clothes.
Bags and accessories all count too.

@jlc - You're not going to dress like you live in the Hamptons because you don't need that type of clothing where you (or anyone else) lives. It's way too dressy for the rest of the country. Great if you were going to the South of France.

Do you have a pair of white jeans? That and sexy high heel sandals with a top that's just a bit dressy can take you anywhere at night. Get blingy long earrings or a statement necklace.

A dress or two might be useful. I'd be looking at Anthropologie or Calypso St. Barth for something a little stylish. You could always go shopping when you get there with your SILs.

But I'll say this. There are plenty of people who live in EH full time who dress in jeans and polar fleece and rarely see the inside of a trendy restaurant or club. But if you're staying South of the Highway then it's a bit different.

The Real Housewives look like Vegas hookers. All of them. Who would want to look like that. Ugh.

Since you came to ask this question, then it definitely bothers you. Don't sell yourself short. Yes, be yourself, but you need a few basics to feel pulled together and happy with your appearance. Nothing wrong with that.

Go for the classic look, and you will be able to incorporate it in your everyday life. You don't think you can, but you can!!!

Old time GW member Magaverde (remember him?) used to say "Decorate for the life you have, not the life you wish you had." And this is true about your wardrobe as well. But it shouldn't mean you can't go out of your comfort zone for one or two pieces, but still be yourself.

I am guilty though of buying things and later asking myself, "And you intended to wear this when…..?" Lately, I am pushing myself to just rotate everything and make a point of wearing everything at least once this summer.

I think Roarah is right on track based on how you describe yourself.

Thanks all. Yes, I just need to find a few new pieces to fill in this gap in my wardrobe. I will feel more comfortable if I'm well-dressed. I tend to spend my money on my house and my DS. We don't dress up and go out! I hate buying things just for this trip, and so I've avoided it and procrastinated, and now it's last minute panic.

@Rococogurl-- yes, it's south of the highway! Walking distance to Main Beach/Georgica Beach. Spent the whole summers there when DH and I were in college. What a strange world it is :-) Great suggestions, thank you. Sundresses have been my go-to in years past. I need to order a few today.

I've observed that uniform in the tri-state area for middle-aged and older ladies in the summer is: sleeveless top, capris, and some sort of loose cardigan or jacket. This outfit is worn with sandals, and the loose cardigan/jacket goes on when you get into air conditioning. Jewelry and purse are whatever's in style at the moment. Put your sunglasses on your head and you're a native!

Your skin needs to breathe in the humidity. Stick with natural fibers, expose as much skin as you're comfortable with, and drink a lot of water.

You might also want to pick up a pair of Gizeh Birkenstocks. They're what fashion stylists wear in the summer.

jlc - Got it. Dresses are good. Another strategy is black + jewelry & sexy shoes. If you could get to the city first you could get what you need in half a day. DD uses yoox. They have a sale but I find them expensive for what I need. Maybe for ideas. Anthropologie might provide something -- their dresses can be good.

Love Georgica Beach. We had house in East for several summers. Also Amagansett. DH didn't love the fishbowl so we are upstate. Yes, strange world indeed but still wonderful in it's own way. Just a lot of work when you're not programmed for it.

For evening wear for someone who is 5'4" and apple shaped, I'd stay away from white slacks/jeans and look for black, navy or chocolate brown linen, then pair with a crisp white cotton shirt/tunic, and sandals.

The way you describe your style, I would look at Anthropologie.

Head to the Chico's nearest you. Buy a long, casual dress, a pair of capri's and some linen slacks. They have a great sale going on now If you look at how they coordinate outfits you will find that you can buy just a few pieces, sure to be appropriate for the Hampton's. They also have great costume jewelry: http://www.chicos.com/store/

I have seen linen beach pants at tjmaxx and even Target if you are on a budget. Tunic's similar to the lily Pulitzer are every where now, Chico's, Dressbarn etc. At TJmaxx they often have linen beach coverup dresses very similar to the Tory Burch I have for much less too. I think you can find a beach look you like and than shop the look at less expensive stores. I live on the coast so I do look for longevity and have had good luck with the brands I mentioned but I have had great beach pieces from Target and TJ's too.

I would try to pick (mostly but not all) shirts you could still wear at home so you don't waste a lot of money. My first stop would be The Loft, nice stuff for the price and their pants are comfy. Next stop would Banana Republic and lastly, Anne Taylor to look at tops. If you would wear a dress normally when out and about look in the above shops. If not, don't bother! I have done the casual dress thing a few times and never end up wearing them because I do not wear them normally. I have to have things that are comfortable on top of everything else. These are nice but maybe not with the skin tight shorts.

I don't think wanting to look one's best means you "are not being yourself". And I do think we all know people whose look we admire, and who might even make us feel shabby by comparison! That is what I hear this poster saying. It's very normal.

When you look good, you feel good. I think the OP will have a better time if she finds a few things she really feels and looks good in. They needn't be expensive. Everything is on sale now anyway. And even cheap stuff looks good when it is brand new.

JLC, treat yourself. Ask a friend or a salesperson for help. We are operating blind here with ideas, makes no sense. But I do hope you board the plane feeling radiant!

Lots of people look put together because of their accessories and how they are coordinated. A large pretty scarf tied off of one shoulder, a great pair of earrings, a bag with details, a statement necklace (not all at the same time), those flip=flops that someone posted a link for. If there is a Winners nearby I'd go there. There is a Winners right by Anthropologie in a mall near me. My local Banana Republic only goes to size 6 (or so it seems).

I get you on the local dress code. I'm in the PNW (Cdn side) and if I have to go anywhere that requires something other than jeans and gortex I have a problem.

Blfenton BR goes up to size 16 in bottoms but only up to a XL in most tops which is weird.

I definitely would not go out and spend alot of money on vacation clothes, especially if these are things you will not wear at home. I love Rococogurl's advice and the shirt that Funky shows. Since you mention you do not do well in heat/humidity, I would not do the long sleeve tunics. I wouldn't do jeans either unless you can find some light weight ones. I would look at some more pieces @ JJill. I would buy a couple of nice tops, a pair or two of a comfy, trim, cropped pants (not skinny but straight cut will be flattering to your height and shape) and perhaps a maxi dress or skirt or a knee length dress.

jlc I just wanted to share that I did some linen beach shopping at JJill in May for a Florida beach trip. I too was vacationing with DH family and would be surrounded by fashionistas. I have gained about 40lbs in the past 3 years all in my stomach. I have never been a JJill shopper but was very pleasantly surprised at the easy fit of the linen things. I had to size down... I signed up for emails and have been hit with sales and used the 40% off with the sales. The thing is they shipped immediately! I could return things to the store if need be. I did go to my local store but the prices were better online.

My daughter thinks JJill is too grandma hippy slouchy but with my belly that style hides a bit...

I was in Old Navy today and they had a good selection of tunic tops, beach cover ups and summery dresses. Most things were around $25.

I rarely go to Anthropolgie nd whle I love browsing in there, their clothing prices (well everything but particularly clothing) are so high! I think I would look online at Chicos (which is having a very good sale now as someone else mentioned) and other places for inspiration and then head to Target and TJMaxx- Marshall's Ross. I agree that you want to feel confident and comfortable and that sometimes a few new items can really spark that feeling. A few new tops, those Donald Pacquette flip flops that Mtn posted are adorable and cheap! I like the idea of linen but don't you all find it to be so creasewinkle friendly?

Old Navy has wonderful wider leg linen pants with a yoga waistband. I'm in love, not a style I thought I would like, but flattering and comfy. You can order them in all sizes including petite online. The stone/putty pair is particularly awesome. I wear them with an ultralight weight black top that covers my bum with 3/4 sleeves and a funky necklace or scarf. I feel put together and chic in them!

I second, third, and fourth j.jill! I've almost replaced my entire wardrobe with wonderful pieces - all on sale too.

You just missed 30% off all sale merchandise with free shipping over $100 - go to their site and get on the mailing list. Sometimes, they even have 40% off the sale prices.

My latest haul was delivered today - 4 $79 sweaters & 3 $29 tanks for $105 plus tax.

When I get their catalog, I rip out the items I like and when sale time rolls around, if the price is right.... they're mine.

This is the kind of stuff I stress needlessly over. You'd think at my age I would no longer give a rat's ass what people think of my clothes, but it must have been bred into me. :(

These people are your family. They know you. They know you're from the casual West (me too, long live the West!!!). It's summer. You're on vacation. I'd dress however you normally would when you want to look a little nicer than usual, like you put a little more effort into it. I do that a lot. Left to my own devices it would be jeans, t-shirts and flip flops. With a little effort, I can look like I tried harder. :)

Treat yourself to one or two new things that you like, that suit your lifestyle, that you will wear back home. Have fun on vacation and be yourself.

This store is near my work, and might give you some ideas:

Harper Greer

Their website in not set up for mail order (though they say you can call).

I have one SIL who is very cutting edge, wild trends, skimpy clothes; one SIL who is a professional shopper at JCrew; one who lives in South Beach (Miami) and dresses that way; and one who is very traditional New England preppy style. DH's parents are very traditional and low-key, linen & khakis, etc.

Ok, so this turned into a rambling post with no real solutions. I'll just be who I am, and wear what I'm comfortable in, as usual! Looking forward to unscheduled days of beach, naps, drinks, etc!

You found the solution in just being who you are. Reread the description you gave of your SIL's and add yourself with your casual laid-back West coast styling. ;) Have fun!!!

Linelle, I still do too. But, I think it keeps us current and still in the game, so to speak. Even though I might stress, trying to put together the right look, I do remind myself that there will be so many totally different fashions statements at the same party or event.

I agree with you in that "with a little effort, I can look like I tried harder."

Isn't JJill mostly for older women? I mean there is some nice stuff there but Jlc is a 43yr old spring chicken. Forty three is really thirty three ( or at least 35) these days.

Based on this thread I visited my local JJill today, thinking I'd get a sense of how their clothes fit and sizes run. There were three saleswomen there. They would not stop telling me how great their sale prices were and was I finding what I was looking for? How I wanted to say, would you please leave me the eff alone?!! I liked their white linen shirt but didn't feel like parting with $50 after having been badgered the entire time I was there. It was almost as bad as Coldwater Creek in that respect.

justterrilyn, I'd say JJill is for mature women who want to look crisp and linen-y.

Thanks again to all of you. I've been in a whirlwind of shopping, just waiting for some online purchases to get here. I'm also preparing for a big job interview this week, ugh!

Justterrilyn, bless you, it's my birthday today, and that made me feel great! Thank you :-)

Well Happy Birthday! I loved my forties! Four and a half years from now I'll be sixty...sheesh, how did that happen to little ole me? Anyway, enjoy this time because it's really when women look most beautiful.

Happy birthday! I also loved my forties and my fifties were even better. Sixties are okay, even good most of the time as long as I don't accidentally hit the reverse view on the i-pad camera! Ha. Hope you have a wonderful day and best of luck on your interview!

Ditto 40's being fabulous and 50's being even better. 60's are...I forgot what I was saying :-). Happy Birthday! And good luck on your interview!

Happy birthday jlc712! 60's have been good to me so far! I just got a new job, after going through 3 rounds of interviews. Wishing you good luck on the big interview! The clothes are nothing to worry about, if you put it in perspective!

Happy Birthday!

Happy Birthday! Sometimes just having something new to wear perks up how your feel about your style and self confidence. Enjoy your vacation!

Happy Birthday, jlc712! You are about my DD's age and she shops at Ann Taylor loft a lot. Stay out of JJil and Chico's. You don't need that. Heck, I'm in my 60's and I don't go there!

Wow.. I am a little surprised by how many see JJill as "old lady" clothes. I've been wearing JJill casual wear since my early 30s (I am 50 now). There's no question that the store has changed over the years-- and I do think it leans a older these days-- but there are still some great pieces! I absolutely love their "perfect tank" and the elliptical tees. I also like the gauzy flowy boho tops. They don't carry my favorite linen pants anymore but I do have a few pairs of their boyfriend jeans. I don't think I dress "old lady" at all LOL-- in fact, there are some who would say I dress too young for my age! The store seemed like a good fit for JLC's slightly hippie boho style, her budget and her body shape... oh! and for the weather she'll be facing.

My bigger issue with JJill is the sinking quality (and with many other stores!). I first started shopping there because they had all natural fibers-- no more. I still stick with their all cotton (or linen.. or cashmere) pieces but now I know I need to check fabric content.

Happy Birthday, JLC!! Hope you had a fabulous week and hope you are happy with your new purchases!

I used to wear JJill as well but their styling has become too mature for me. I still occasionally get a blouse but find myself returning them too often.

Like anything else, if you can find that one cute top or perfect pair of pants, every store is worth a look at.

I am not that lucky at JJill, but keep circling back as my options being a petite are limited. Most of my clothes are bought from Loft and Ann taylor websites.

Right now i am waiting for a gauzy sleeveless print top to go on sale. THey don't offer sales as often as Ann Taylor and Loft, so I will keep checking my shopping bag to see if it is reduced.

Add my best wishes too, JLC!

Funny how we see things differently. I love the easy, modest looks of j.jill but, then again, I've never been a body conscious dresser. I don't find it any more 'old lady' looking than Eileen Fisher, which is totally out of my comfort zone, price-wise.

Now, to me, Chicos reeks of old lady from Boca and Coldwater Creek was/is (online only now) super old lady to me.

One of the blogs I follow alerted me to a brand that I've blown off in the past because of their lack of style - Dress Barn - still have some so-so styles but tons of adorable dresses and tops at prices most people can afford.

Hey Jlc, this stretch cami in nude was so handy during my vacation. Even though this is stretch I buy the next size up. This one from Ann Taylor is very comfortable. Your shirts will fall nicer, good for under shirts that are maybe a tic too sheer ( thin shirts seem to be the norm these days), and, you can get extra use out of tops before laundering. At $29.50 you can't beat it as the second one is 50% off. They wash out easy and dry fairly fast.

JJill styles have definitely changed, but you can still find the occasional nice piece. The past couple years I've been buying their cardigans at greatly reduced prices. Just grabbed one today.