# Fashion for the guy not quite 50...



## movealong

I am now single. She moved out yesterday and the divorce should be final in 50-60 days. 

I want to refurbish my wardrobe, but I don't even know where to start. I am going to get stuff I like, but I don't want to stick out like a new divorced guy, lol! 

Any suggestions?


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## MSP

Bleach your hair, get some gold chains . . . 

How you dress will reflect your personality and environment, plus who you want to attract. So, there are general guidelines for certain outcomes, but it is also quite individual. Here are a few general guidelines:

 Always dress up a little more than you need to. You'll stand out in a good way. So, if other guys will be wearing jeans and t-shirts with runners, wear a collared shirt and leather shoes. 
 Wear stuff that fits! Expensive poorly-fitting clothes just looks like you have money, but no style. Get fitted for the good stuff, if you buy a suit or nice shirt. Don't just buy these off the rack and take them home. 
 You can't really go wrong with a plain dress shirt with a good black jacket and black leather shoes. Pants can be nice jeans or dress pants. 
 Dress a little younger than your age, but not like you're 20-years old. 
 Look for stylish people in your age group and see what they're wearing. At your age, guys like George Clooney and so forth can be good guides. Check out some magazines. 
 If you live in a small town, go to a big city to buy clothes, for two reasons. Firstly, there will be a much larger selection of decent fashion, rather than the chain store hell that infests smaller cities; and secondly, you'll be able to set yourself apart where you live. I live in a small town, but I used to travel all the time for work and bought clothes when I was away in large metro hubs. Girls at home compliment me all the time on my clothes. Guys hear and ask where I bought them, then look stoically annoyed when I tell them it was some city on the other side of the country, or even on the other side of the world. Also, being travelled is sexy, even if you drive.
 Know your style and buy clothing that reflects your personality. Are you loud and outgoing? Buy brighter clothing with bolder patterns. Are you quiet? Buy subdued colours with plain or no patterns. The packaging should match the contents or girls will get a feeling of dissonance. 
 Match your environment somewhat. E.g., if you're a farmer, chances are that an Armani suit might just make you look lost.

That's about it for general rules, off the top of my head. Other than that, if you can give us a bit of insight into your situation for environment and personality, I can give you more specific tips.


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## 6301

What ever you do, don't buy plaid shorts, Hawaiian shirts and if you do wear shorts don't wear black socks and black tie shoes. And none of of those cool garters to hold your socks up.

P.S. No Speedo bathing suits either.


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## movealong

Thanks! 

I am 48 and look like I am late 30's early 40's. I am bald because I don't want to mess with hair implants or the creams that are 'supposed' to grow hair. I just shave it every other day.

Ideal/goal weight is 175-180, and I am down to 198 so far. This week starts a physical training regiment that will include walking, and some HIT to get some cardio and build stamina. By the end of the summer I want to be working out with weights to get some tone back to my arms, legs and stomach.

Style? I can dress for any occasion, but generally like khaki shorts and a pull over collared shirt. No black socks or garters with sandals, or speedo swimsuits!

My 11 y/o daughter may be able to help me pick out clothes, LOL! Since I will be the primary guardian, she can go with me shopping. 

I appreciate the feedback.


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## 6301

No hair in the can either.


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## Fenix

Pull over collared shirts and khakis shorts scream boring. Please don't tell me they are pressed? 

What is your life style like? What region of the country do you live in? What do you absolutely hate to wear or roll your eyes when you see other men wearing it?

Make sure your clothes fit properly and are not too baggy or short in the case of pants/shorts. Shoe wise, ditch the running shoes. Think about mocs and/or bucs. Don't be afraid of color, but make sure that you feel comfortable in it.


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## MSP

movealong said:


> My 11 y/o daughter may be able to help me pick out clothes, LOL! Since I will be the primary guardian, she can go with me shopping.


It will be nice to include her in other activities, but for this, if you take anyone, take two women around late 30s to early 40s to help you pick stuff out. They will have a far, far better idea. Having two women rather than one will create a better dynamic, too. One woman might think, "Is this a kind of weird date? Does he like me? What are we doing--what does it mean?" And she might be cautious or simply put you in clothes that she herself likes. With a second woman, they'll loosen up, play off each other, you'll all have more fun and you'll end up with better clothes.


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## movealong

They're not pressed, lol!

Thank you Fenix and MSP for the tips!!


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## Shooboomafoo

I hear you on this. Early forties myself, and Ive always been in a band, so... most of my "style"? is split into two categories. Work stuff and Fun/weekend stuff.

I haven't had the pleasure of a few extra coin to really shop around. I admit, the pathetic nature of tossing a few pairs of jeans in the cart in between the eggs and milk...


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## Jellybeans

I love fashion threads! I wish I could personally take you guys shopping. I had so much fun putting together Arbitrator's date outfits (virtually).

You need:

A good pair of jeans that fit well (and are long enough-not too tight or baggy). A couple of nice t-shirts, a nice polo shirt (long sleeves), a blazer, some good casual shoes and at least one dress up outfit/shoes. And new cologne. SO you can start making new olfactory memories! 

Jeans: 
http://img03.taobaocdn.com/bao/uploaded/i3/T1qWfuXoJdXXXf8L6b_124102.jpg

Sweater

http://img05.taobaocdn.com/bao/uploaded/i5/T1NbayXjRsXXcS837Z_032451.jpg

Blazer/jeans/casual shoes

http://images2.chictopia.com/photos...-m-jeans-h-m-blazer-club-monaco-shirt_400.jpg

Classic summer look

http://images0.chictopia.com/photos...e-shorts-white-polo-hollister-t-shirt_400.jpg

George Clooney nails it:

http://www3.pictures.zimbio.com/pc/George+Clooney+arrives+Sarnico+Italy+film+phi1hRsv6Eil.jpg


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## Fenix

Jelly, you are too funny. I agree on your choices, except for the jeans perhaps. They look a bit like mom jeans...too high waisted or something. Maybe it is the tucked in shirt?

George does nail it, but I also think the dude with the beard looks pretty hot too.


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## Jellybeans

Fenix said:


> Jelly, you are too funny. I agree on your choices, except for the jeans perhaps. They look a bit like mom jeans...too high waisted or something. Maybe it is the tucked in shirt?


It's the shirt. That shirt is horrendous. I like the cut and how they aren't too big/skinny. 

Re: Mom jeans! :rofl:

When in doubt, defer to Clooney!


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## movealong

Thanks, Jelly! I have a better idea of what to go for now.


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## Fenix

Jellybeans said:


> It's the shirt. That shirt is horrendous. I like the cut and how they aren't too big/skinny.
> 
> Re: Mom jeans! :rofl:
> 
> When in doubt, defer to Clooney!


Yeah, I dislike skinny jeans on men, or the baggie look. Well fitted jeans with super cool boots or shoes (adore monk straps!)


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## Jellybeans

Oh you mean skinny/baggy jeans like this? 










What in the HELL is he wearing? Seriously, this one is even worse:

http://i.imgur.com/dDY3iic.jpg


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## Fenix

The MC Hammer'ed look!


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## Pbartender

movealong said:


> Any suggestions?


This website is your new best friend... Dress & Grooming | The Art of Manliness ...search the archives for more.



MSP said:


> Wear stuff that fits!





MSP said:


> Know your style...


These are without a doubt the two most important things you can do. No matter what you wear, you won't look good and you won't feel comfortable if it doesn't fit properly. And no matter what you wear and how well it fits, you will never have the confidence to look good, if you don't truly think you look good in what you're wearing.

How Should a Suit Fit? Your Easy-to-Follow Visual Guide | The Art of Manliness


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## Rowan

Just a couple things I've seen 40+ aged men do badly of late:

Skinny jeans, or jeans in any color other than some shade of blue or black, should - with extremely rare exceptions - never be worn by a grown man. 

Be careful that if you wear pleated pants, they fit you perfectly so that the pleats don't gape and make you look heavier. 

If you roll the sleeves of your button-down shirt up, don't roll them up too far. It's not a short sleeved shirt, and rolling or pushing the sleeves above the elbow isn't ever going to make it a short sleeved shirt. It just starts to look puffy and/or goofy. About midway between the wrist and elbow looks best.

Make sure the sleeves of your short sleeved shirts are long enough. Cap sleeves are not a good look on most men.


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## Wolf1974

I admit I am fashion challenged. When I started dating I had something called Dad jeans that apparently were not good lol.

Find a female friend or family member you trust and have them take you shopping, A couple hundred in and I had a brand new wardrobe and felt good. But I wouldn't have picked out most that stuff for myself to be sure . 

It apparently has worked. My GF can look at anything in my closet and just say...pre divorce...post divorce...she is 95% accurate.


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## Pbartender

Rowan said:


> If you roll the sleeves of your button-down shirt up, don't roll them up too far. It's not a short sleeved shirt, and rolling or pushing the sleeves above the elbow isn't ever going to make it a short sleeved shirt. It just starts to look puffy and/or goofy. About midway between the wrist and elbow looks best.


How to Roll Up Your Shirt Sleeves | The Art of Manliness










I wasn't joking about that website being your new best friend.


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## movealong

I really appreciate all the great advice and links!! 

Now I just need to find a lady friend or two to go shopping with me, lol!


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## 3Xnocharm

Collared, button up shirts and khakis...BOOORRRIIINNGGGG. Zero sex appeal. Go with jeans, jeans that fit and please stay away from the ones with heavy embroidery on the pockets! Fine for us ladies, but hideous on guys! Oh and avoid the high waisted ones, too. Also with most shirts, dont tuck them in! Makes me think of Alan on Two and a Half Men! He is a pretty good example of the boring look to avoid.


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## angelpixie

Movealong, I'm a woman, but in your age range. Divorce was a chance for me to really find out what I liked, and to stretch convention a little. In my marriage I had become pretty mousy at one point. Towards the end, I had started to pay more attention to what looked good on me, rather on what 'did the job.' After I was on my own, I took that as an opportunity to try a lot of different things until I found my own style. As others here have suggested, too, you should do the same. 

You can have style and look up-to-date without looking foolish, no matter what your age is. If you haven't really paid attention til now, take some time and just look up some websites for department stores, for example. Make note of things you like and don't like. Dress for your body shape. Something that looks good on one guy might look hideous on another, just as is true for women.

After you have a few ideas, hit some stores and try some things on, whether you have someone to go with you or not. If you have nice thrift stores around, pick up a few things and give them a road test. If you end up not liking them after all, you're not out much money. Rinse and repeat til you have what you like. This is about you. Don't dress to impress someone else. Dress to express who you are, in the best way for you. There will be someone out there who will appreciate it. Some women really like collared, button-down shirts with rolled sleeves and non-pleated slacks, for example, and others really don't.


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## Fenix

Wolf1974 said:


> I admit I am fashion challenged. When I started dating I had something called Dad jeans that apparently were not good lol.
> 
> Find a female friend or family member you trust and have them take you shopping, A couple hundred in and I had a brand new wardrobe and felt good. But I wouldn't have picked out most that stuff for myself to be sure .
> 
> It apparently has worked. My GF can look at anything in my closet and just say...pre divorce...post divorce...she is 95% accurate.


What is funny is that if you look in my X's closet, you will see the same thing...just in reverse. He always thought he had fashion sense, but he didn't. Whenever we went shopping, even if it was for me, it turned out to be for him.


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## Jellybeans

Sorry--I had to share this. I keep coming across insane Justin Beiber outfits.

Whatever you do, movealong, do NOT dress like this guy:


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## movealong

So, is that a potato in your pants, or did you drop a deuce Justin?

LOL! I will never go out dressed like that! Not even for Halloween!


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## angelpixie

It looks like he's wearing a sweater on his legs! :rofl:


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## Ikaika

Jellybeans said:


> Sorry--I had to share this. I keep coming across insane Justin Beiber outfits.
> 
> Whatever you do, movealong, do NOT dress like this guy:



Are you saying a 53 year old like me can't pull off that look 

Btw, what is he wearing and who is Justin Beiber? 

Get off my lawn :rofl: now where did I leave my keys?


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## Jellybeans

LOL, Dre! :rofl:


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## Rowan

As the mama of a teenaged boy, let me say that I just want to smack Justin Beiber every time I see a picture of him.


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## Dread Pirate Roberts

I'd also recommend this website:

Effortless Gent

I always liked this article in there:

Sartorial Evaluation: How to be stylish in your 40s and beyond | Effortless Gent


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## movealong

Well, the fashion shopping today is not for me, but for my daughter. 

Several months ago I bough tickets to the ballet to see Swan Lake for me and STBXW. To go to the ballat (particularly Swan lake) was one of the things on her bucket list. I was doing everything I could to rebuild our relationship at the time, and I had hoped by doing this it would help in that regard. Obviously it didn't, lol.

Well, since the ballet is on STBXW's bucket list and not mine, I asked her to take DD3. She agreed, but several times has said that I should be the one taking her. While I agree with her in a way, I think it is better for STBXW to take her. It will give them both a lasting memory to share, as well as giving me a part of the memory to share by getting DD3 ready for the ballet.

So today, I embark on a Single Dad Adventure (SDA): Dress and shoe shopping for DD3 to attend the ballet!

I am really looking forward to this SDA!! Yesterday we went and had her hair cut and styled, today is dress/shoe shopping, and tomorrow we are going to get her nails done!

Luckily for me, the ladies at the hair salon had some very good ideas on dresses and where to shop, so when I pick her up from school, off we go! 

I can't believe how excited I am to go dress shopping! LMAO!


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## EnjoliWoman

I hope she enjoys it - 3 is a bit young for the ballet - I'm not sure she'll really remember it, either.  Wait - nails... does 3 mean your third daughter? usually DD3 means "dear daughter [age] 3 "

I'm confused. 

People here unfortunately don't often dress for the theatre. There is a generation that does, a younger generation that tries and a middle generation that doesn't seem to mind khaki pants and golf shirts.


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## movealong

DD3 = darling daughter #3. 11 years old.


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## poppyseed

movealong said:


> I want to refurbish my wardrobe, but I don't even know where to start. I am going to get stuff I like, but I don't want to stick out like a new divorced guy, lol!


Funny, that's the first thing I used to do and am still doing. It's good to look stylish and care about how you look. I must admit I wasn't really paying attention when I was married. Great to be single again.


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## Bluebirdie

LOL you made me smile! thank you


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## movealong

OK, so this weekend I went to one of the multi-class HS reunions. My sister's class was there as well as a few people from my class. I thought I was doing pretty well dressing myself:

Nicely ironed buttoned short sleeve shirt.
Blue jeans that fit well (no dad jeans!).
One ring on my right hand.
My nice watch.
A simple gold chain (no big bling, thanks!).
And a pair of brand new Nike's.

First opportunity my sister has, she takes me aside and says "You've got to get some different shoes. White Nike's are out of style."

I said "See, that's the kind of s**t that happens when I have been out of the dating scene for 14 years!"

So, if the standard, for my day, is no longer a nice pair of sneakers, what the heck kind of footwear am I supposed to have?


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## Jellybeans

When in doubt, refer to George Clooney:

http://www.x17online.com/images/photo-sets/conv/GClooney060912_X17/GClooney060912_11-full.jpg

These sneakers are nice. It's all in the style.

http://www.winterfashions.net/pictu...or-men-clothing-2013-2014-t-shirt-469x550.jpg

And Gosling does a pair of jeans/shoes well here:

http://www.x17online.com/images/photo-sets/conv/rgoslinglax061711_X17/rgoslinglax061711_23-full.jpg

Keanu Reeves (also, my Hollywood boyfriend):

http://qph.is.quoracdn.net/main-qimg-445bd80f794bbf8daa04cb8560e78eb1?convert_to_webp=true


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## movealong

Jellybeans said:


> When in doubt, refer to George Clooney:
> 
> http://www.x17online.com/images/photo-sets/conv/GClooney060912_X17/GClooney060912_11-full.jpg
> 
> These sneakers are nice. It's all in the style.
> 
> http://www.winterfashions.net/pictu...or-men-clothing-2013-2014-t-shirt-469x550.jpg
> 
> And Gosling does a pair of jeans/shoes well here:
> 
> http://www.x17online.com/images/photo-sets/conv/rgoslinglax061711_X17/rgoslinglax061711_23-full.jpg
> 
> Keanu Reeves (also, my Hollywood boyfriend):
> 
> http://qph.is.quoracdn.net/main-qimg-445bd80f794bbf8daa04cb8560e78eb1?convert_to_webp=true


Thanks for the tips, with photos! LOL!


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## BeachGuy

movealong said:


> First opportunity my sister has, she takes me aside and says "You've got to get some different shoes. White Nike's are out of style."


Oh crap.


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## U.E. McGill

Brown shoes with a brown belt for jeans. Chuka's or something similar. Zappos is great for a guy. Stay away from black dress shoes and jeans. 

Also one more tip, shirts with tails get tucked in, shirts that are square can be left untucked.


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## U.E. McGill

If you wanted to go the sneaker route, try some chucks next time. But wear them with confidence.


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## Dread Pirate Roberts

movealong said:


> So, if the standard, for my day, is no longer a nice pair of sneakers, what the heck kind of footwear am I supposed to have?


Sneaks are fine, it's athletic shoes you need to avoid. Get a pair of canvas sneakers from Sperry, Vans Authentics, etc.

Also find a nice pair of desert boots - can't go wrong with Clark's - or chukkas, and maybe a pair of bucks.


DPR


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## movealong

So, I went down and bought some new blue jeans, a few t-shirts with no logos or pictures on them, and a nice pair of loafers. I was going out the other day and put on a dark brown t-shirt with the new jeans and loafers and went in to get my daughter so we could go to the store and she said "Who are you meeting? You look good!"

I got several approving looks walking through the store so I know the advice here helped! Thanks!


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## U.E. McGill

Confidence wears like a good cologne. A little goes a long way.


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## bravenewworld

Since it's summer right now I really love a guy in linen pants - white, off white, or beige. Polished but casual. Jeans are cool too, I tend to prefer the darker washes on men.
Linen Pants
Jeans

Linen shirts are cool too (but not with matching pants - no linen on linen action!) I also likely brightly colored/fun polo shirts. 
Fun Polo


I prefer some really cool cargo pants to khaki's. Also I think guys look great in classic "dude gear" like leather bomber jackets and vintage army M65 style jackets. These can be found at vintage shops. Look for something fitted to you, not too tight and not too bulky. Aviator style sunglasses are also sexy on men. 
Cargo Pant
Leather Bomber
M-65 Jacket
Aviator shades

Shoe-wise besides the classic leather I think Sperry Top-siders are the perfect "dressy casual" shoe. No puffy sneakers! If you do want to wear sneakers because it's active date, I suggest a pair of cool trail runners. Saucony makes some nice ones. 
Top-Siders
Trail-runners


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## movealong

Awesome tips! I appreciate it.


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## Mr The Other

3Xnocharm said:


> Collared, button up shirts and khakis...BOOORRRIIINNGGGG. Zero sex appeal. Go with jeans, jeans that fit and please stay away from the ones with heavy embroidery on the pockets! Fine for us ladies, but hideous on guys! Oh and avoid the high waisted ones, too. Also with most shirts, dont tuck them in! Makes me think of Alan on Two and a Half Men! He is a pretty good example of the boring look to avoid.


I write as a European who has only lived in the USA for a couple of years. My opinion is only my impression. However, the reason smarter tends to be boring in the USA is there is a very boring safe territory. This involved a simple pattern on a coloured shirt with buttoned down collars, sports jacket with kharki or chinos with turn-ups. This is a cliché of what an American gentleman wears when making an effort, but is not too sure of himself. 

Our OP wants to dress to impress, I suspect. Therefore, he must be warned against the above boring path and you are right to do so. However, if he has the guts, there is another way. Dress swanky. Find smart pants, and smart pants are made of wool and adjusted to fit your leg length. Avoid turn-ups on the trouser leg (unless you have stork like legs). 

The next step is how you define your style, swanky is one, professorial is another. 

For swanky, very smart shoes and Italian style jacket (probably a size smaller than you think, the Art of Manliness guide is good here). You will look sharp, stick to dark plain pants and avoid pleats unless you are distinctly overweight. Keep the shirt white, men avoid this, but it is the classic.

For a more proffy, look to the tweed jacket, but get a British/European fit, stick to the white shirt and avoid button down collars. Accept the Oxford brogue as your shoe of choice and just ensure the shoe and best match.

But avoid the clichéd smart casual look that blights the middle aged American man. Xnocharm and I agree on this. THere are three options.

Edited to add: This is dressing to impress and attract. That involves standing out somewhat. If you do not wish to stand out, then there are many better posts on this thread.


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## movealong

Great tips, MTO! Thank you!


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## Hardtohandle

Don't be afraid to be honest in the store.

Long story short ( I will try as I am long winded )..


Lost 85 LBS in 5 months.. Lost maybe 50 in the first 3 months.. Depression plain and simple.

I needed full set of new cloths and had no clue what might size would be. 

I went to Macy's and was looking for a Jacket as it was around winter time. But I needed a stylish jacket as my friends put it. 

I Literally put on a few jackets that I thought looked real cool and sent pics to my friends. We settled on one or two jackets. The one I liked ended up being on a discount rack accidentally. I never looked at the price as it had no tag.. 

They found the jacket and it was $400.00.. I was talking with woman and just told her first time I am buying clothes for myself in close to 15 years.. She understood and said been there done that.. It gets easier as time goes by..

She then went to the other woman behind the register and told her the jacket was on the discount rack and they had to honor it.. I then reactivated my Macy card and took my Ex off of it as well and received another discount on top of the 50%.. I think I ended up paying $ 175.00 for the jacket.. 

What I can attest to is I used to dress like a slob because I had no one to impress and then after my divorce went to dressing like steve carrell in stupid crazy love (at least somewhat) and it worked.. No fashion model here, but even I noticed the attention sometimes.. 

So dressing nice works.. 

Payless for sneakers.. I bought gray, black laced sailing type sneakers for 20$ a pair.. $ 40.00.. I bought a brown knock off of another sneaker style for $30.00.. For $70.00 I have 3 pair of sneakers I can switch on and off from depending on what I am wearing.. 

Nonetheless the current G.F. commented that was one of things she hooked her to me, that I could change my sneakers with what I was wearing and that stupid jacket made me look hot.. 

You need to know your look.. Even at 235, I could use to lose 10 to 15 more and tone up.. I am much better dressed than naked.. I don't wear tight fitting shirts as I have man boobs.. I always had them even as a kid.. I'm a bit flabby and need to tighten up. So I didn't want to be that person who thinks they lost tons of weight and NOW thinks they can wear these tight cloths.. When the reality is they are still out of shape or fat.. It just hurts your image and we all know people WILL JUDGE A BOOK BY ITS COVER.. Especially in a bar or a first date.


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## southbound

Jellybeans said:


> Oh you mean skinny/baggy jeans like this?
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> What in the HELL is he wearing? Seriously, this one is even worse:
> 
> http://i.imgur.com/dDY3iic.jpg



I just threw up on my keyboard!


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## Chuck71

I wish it was as easy as it used to be. As a late teen, I used a simple 

philosophy. I would purposely mismatch my clothes before going to the mall.

I saw it as this, 'A girl would think...that poor guy must be single because there is no way his g/f would let him go to the mall dressed like that.'


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## SurpriseMyself

Don't: wear white tennis shoes, wear the same style Levi's or Lee jeans you wore in high school, own any clothes from the last millennia (unless from a vintage shop purchased under advisement)

Do: get new shoes, buy current, dark wash jeans, have clothes tailored if needed, save the old t-shirts for mowing the grass.

Generally, you should dress your outside to match your inside. Personally I find the khakis and polo look a snooze Fest, but maybe you are just a conservative guy, so that matches who you are. 

Make clothing choices that best reflect who you are (and let's hope that isn't sweatpants!!!)
_Posted via Mobile Device_


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## DayOne

Good thread! Some great ideas for an 'old' guy like me (47). One of the first things i did on D-Day was to go and buy some new clothes (hmmm, maybe i am in touch with my feminine side!  ). Black Chinos and a fitting classic white shirt. 

Payday is rolling around. Might be time to hit the stores again!


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## Fenix

DayOne said:


> Good thread! Some great ideas for an 'old' guy like me (47). One of the first things i did on D-Day was to go and buy some new clothes (hmmm, maybe i am in touch with my feminine side!  ). Black Chinos and a fitting classic white shirt.
> 
> Payday is rolling around. Might be time to hit the stores again!


Yep. I have to say that I really like well fitting black (or dark grey) t shirts and nicely fitting jeans, esp if you have nice legs. And boots. Get some boots.


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## bravenewworld

Mr The Other said:


> I write as a European who has only lived in the USA for a couple of years. My opinion is only my impression. However, the reason smarter tends to be boring in the USA is there is a very boring safe territory. This involved a simple pattern on a coloured shirt with buttoned down collars, sports jacket with kharki or chinos with turn-ups. This is a cliché of what an American gentleman wears when making an effort, but is not too sure of himself.
> 
> Our OP wants to dress to impress, I suspect. Therefore, he must be warned against the above boring path and you are right to do so. However, if he has the guts, there is another way. Dress swanky. Find smart pants, and smart pants are made of wool and adjusted to fit your leg length. Avoid turn-ups on the trouser leg (unless you have stork like legs).
> 
> The next step is how you define your style, swanky is one, professorial is another.
> 
> For swanky, very smart shoes and Italian style jacket (probably a size smaller than you think, the Art of Manliness guide is good here). You will look sharp, stick to dark plain pants and avoid pleats unless you are distinctly overweight. Keep the shirt white, men avoid this, but it is the classic.
> 
> For a more proffy, look to the tweed jacket, but get a British/European fit, stick to the white shirt and avoid button down collars. Accept the Oxford brogue as your shoe of choice and just ensure the shoe and best match.
> 
> But avoid the clichéd smart casual look that blights the middle aged American man. Xnocharm and I agree on this. THere are three options.
> 
> Edited to add: This is dressing to impress and attract. That involves standing out somewhat. If you do not wish to stand out, then there are many better posts on this thread.


I worked in fashion for many years. I like the above suggestions BUT one thing I have to note is that European fashion tends to be a little more formal and costume-ish while American fashion is more unstudied, casual, and cool. 

Neither is better per se but I've noticed with outfits like the one described above, you tend to notice the outfit. With American style, the point is to notice the man.


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## Mr The Other

bravenewworld said:


> I worked in fashion for many years. I like the above suggestions BUT one thing I have to note is that European fashion tends to be a little more formal and costume-ish while American fashion is more unstudied, casual, and cool.
> 
> Neither is better per se but I've noticed with outfits like the one described above, you tend to notice the outfit. With American style, the point is to notice the man.


A very fair assessment. I am pretty much recommending dressing like a European (or frankly, like me) in the USA, which does mean the outfit will stand out. While I lay out some ideas, it is clearly important that he is himself with it. There is that first step though, of leaving the comfort zone.


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## Ynot

One of the things I did when I was younger was to go to a store several times window shopping. When I did see a clerk who caught my attention I would approach her with a question about something in the department - "Are these on sale too?" type of question. 
The setting made for a casual encounter. The clerk doing her job and you doing yours as a customer. Often times, the clerk would be very helpful. If they seemed especially helpful, you can even ask them to imagine they are choosing an outfit for you to wear on a date with them, what would they pick? You can get some real feed back using that tact and you might meet someone new.


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