How to Stop Dressing Like a Teenager?

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I've been doing a lot of thinking as to why women don't seem to give me the time of time and yet when I last wore my suit the women were literally drooling over it and commented over and over again how good I looked. It took me until now to realize that no woman is going to see me as Husband material when I look like a typical 16 year old kid with a ball cap, shades, jeans and a hoody on. Bottom line is that I HATE dressing up and dislike wearing a collared shirt and usually wear a T-shirt in the summer with athletic shorts and sneakers. I feel comfortable around teens but I know as a man in his 30s I have to learn to look my age.

I don't have a whole lot of "nice clothes" outside of my suit and I H-A-T-E dressing up and feel very awkward doing so. Any suggestion on how to overcome this? Any ideas what I should wear and what would attract a reasonably good woman? I honestly don't have any fashion sense whatsoever because my jobs have always required unisex uniforms that were provided.

I'm really not good at that either. Actually that is a bit a concern for me too.

I hate suits too, even if I have been told that I look good in it too. I just find it silly to wear some kind of uncomfortable uniform.

The only advice I could give you is to look beyond your usual clothes and the stereotypical "suit" and other "uniforms". Find some clothes you like that are both good-looking and creative. Help from an open-minded NT is almost necessary to prevent you from somehow dressing in a "weird" and inappropriate way, but if you manage to do it I think you will feel much better dressing in a way that is both something you like and something that looks good than just adopting some random social code. Anyway most of us are better at being genuinely creative than at following implicit social codes.

I know first hand it is easier said than done, but I can't really give any better advice.

Also NT dress codes differ wildly with the location, the social class and other factors. If you want some people here to actually give you some fashion advice you should probably give more details about where you are living and with what kind of people you want to interact (age, social group, etc.)

Try rugby shirts or polo shirts.

Speaking as a woman, to be honest I'm not that drawn to men in suits and shirts and ties, and more drawn to casually dressed men, because I'm a casual person myself. I don't mind getting dressed up for a special occasion like a party or someone's wedding, and, I guess, for a man accompanying me to be in a suit then.

But I'm sort of the artistic type, I don't work in an office, I wear what's comfortable for most of my time, and men who wear suits either by choice or because the kind of life they live and work they do demands it, are usually not my type in more important ways to do with personality, lifestyle, etc. Men I'm actually compatible with, as a person, tend to not have the life or work that requires a suit.

Dress the way you want to dress in order to attract the women who will like and love you for exactly who you are, not someone you're not.

If you really want to dress more formally because you like it for itself, then okay. But if you're only dressing that way because you think it attracts more women -- are they really the women you want? If they don't want you unless you're in a suit?

Personally, a nice pair of jeans and a nice, freshly washed t-shirt is fine with me. Casual doesn't have to look like a teen or attract "not good" women, but in fact can be smart and good looking. It's more about the clothes being kept in a clean and nice condition, than what the clothes actually are.

T shirts
Jeans
Nice khakis -- even shorts

Doesn't have to look like hell.

.

You could take $150, walk into a mall, and walk out an hour later not looking like a teen.

What is hard is finding what is perfectly right for you, taking into account your style and personal preference, age (not looking too young or old), sociocultural identity, climate, location and local fashion culture, not dressing up to much while not dressing down, and so on.

You could easily just check the websites of fashion brands and online stores and fashion websites, and they will have loads of inspiration. Just pick a brand that resonates with you and they are likely to have lots of pictures to inspire customers.

Perhaps you would feel comfortable in chinos, a polo piqué and some clean sneakers, (as clean as they come)? That would look a little more age appropriate but not formal at all and not "in his 40-ies".

I am an older woman with absolutely no fashion sense. I sometimes go to "Dress Barn," and tell them that and ask them to "dress me." They do. I write down possible combinations [down to jewelry, makeup and hair] in a notebook which I sometimes use to get dressed.

I also [because of their help] have developed a sort of uniform of well-fitting nice jeans, tops, fitted jackets and nice boots. I sometimes replace the jeans with a skirt.

No men's clothing at Dress Barn. Do you have a "stylin" brother, cousin, or sister [many women LOVE doing make-overs] who could give you a hand? If money is an issue, you could have your helper assist you in figuring out what looks good on you, write it down and look for the equivalent in a thrift shop [Bring them there as well. You want to make sure that your clothing fits you correctly]

Get yourself some cool hair. Then make sure you keep it from getting all messy, or, sometimes worse, too tidy.

So, when you put your outfit combinations down, make sure you also write down[ with your helper] appropriate weather and ocassions for the combinations [ussually you don't wear the same outfit that you worked out in to go to a funeral] how far to button your shirt, whether to tuck or untuck.

Keep your body and your clothing clean and tidy. And, stupid as it is, that stupid little mustard stain that no one will notice? Or the little hole? People WILL notice. And check for dog or cat hair and get rid of it.

That cologne. Use it sparingly or not at all. And trying to cover b.o. with cologne just makes you smell twice as bad.
keep
Don't forget to keep your nails well groomed. [short, no dirt under nails]

Do not hunch your shoulders. Or stand too rigidly.

Keep your skin as blemish free as possible, don't let your lips get cracked and dry, make sure your teeth are white, and, please, get rid of the uni-brow,

Okay, now that you have all of that down pat, have your helper assist you with accesorizing [better too little than too much] and personalizing your look [into extinct marine life? Wear a megladon tooth on a chain. Something cool related to your interests]

Keep your body fit. Now, that little semi-suppressed smile on your face from noticing all the girls checking you out? Perfect.

I know it's not the advice you are looking for, but have you considered the ramifications of finding a woman who only wants you when you're dressed up? When I met my husband he had on a blue t-shirt and navy blue BDUs. It was 2 in the morning and his hair was a mess under a Cincinnati Reds cap. And he was no less exceptional dressed in a wrinkled EMS uniform and cap than he was in his suit the day we got married. I've seen wrinkled BDUs a lot more than I have the suit and wouldn't want it any other way.

There are girls out there that you don't have to make yourself uncomfortable for. Just like there was a man out there who finds me attractive in cargo pants and an X-Men t-shirt. Don't worry about just finding someone, find one you can be you around and it will stand a lot less chance of ending badly.

I think its safe to say more teenagers than adults dress like me...I don't really care though as I like my band t-shirts, jeans and high top what used to be known as skate shoes(but nowdays its hardly just kids on skateboards wearing them). Not sure if I consider myself a good female for one to be in a relationship with but I don't really prefer well dressed or dressed like a typical adult males...but I don't dress professional or whatever either.

maybe looking for types of females that don't judge so much on looking not as well dressed or whatever would be a good idea.

Thanks for the info so far. I just wanted to touch on a few points:

ouroborosOK: I live in Canada and usually am alone. This type of year it's too cold to really dress properly (especially today. Brr!) but the snow is gone and spring is coming. I usually get along best with young men even though I don't drink. Most of my hockey buddies are 40+ and the ones who I see the most are older than my father. Needless to say I want to change that.
BirdInFlight & EMT Kid: I understand what you are both saying and agree a woman should not want me just because I look great in a suit. However, I have to admit if I were female and saw someone like me walk down the street I would think either he was a "bad boy" or very immature. I just want to look outside what I am inside: a mature, responsible man who wants to find someone to settle down with. Maybe part of it has to do with the low self esteem I got from being told how ugly I was from girls in school. Even though people tell me girls check me out literally all the time (being very tall helps!) I don't see it and they don't approach me. I also have to admit there was this woman I knew for a while who I didn't really pay attention to but once I saw her dressed up my jaw dropped. I never realize how incredible good looking she was. If I wasn't in a relationship already I would have had to chase her just because it highlighted how incredibly attractive she was inside and out and I felt that way even when she went back to looking casual. I just want women to see the "real" me and by dressing my age and not wearing baggy sports T-shirts I hope to attract that kind of positive attention. I remember I wore my suit to work for an hour and the attention I got was unlike anything I have ever experienced before. I even had a girl in a committed relationship blatantly hitting on me for a week afterward to the point people were asking what I did to her to warrant that kind of attention! Both married women and men have told me I would have a girlfriend within hours if I walked around in public with my suit on so take that comment for what it's worth because I've only ever dated 4 women.
vickygleitz: All excellent advice and when I got my suit (at a Men's store) it was a female employee my age who hand picked it and boy did she pick well! Everyone tells me the suit looks downright incredible on me and I have to agree. Unfortunately, most people I know dress either similarly (one guy is in his late 50s and you would think 35 at most!) or they dress in a Gothic manner. My only sibling lives in the other side of the country and my parents have almost no fashion sense. I'll have to try to keep my eye out for a suitable "helper" because I am clueless!
Wind: Good point. I have shied away from Polo/Rugby shirts because I was forced to wear one for many years just like I had to wear a green shirt for a 7 year job 10 years ago and still can't get around to buying green. Ditto for red as well. I guess I need to get over that.
anotherswede:Thanks. I have to admit as embarrassing as it is that I don't even understand what 'chinos' and 'polo pique' are and what classifies as 'clean' sneakers but that's why I created this thread!

Me too. I mostly dress in a t-shirt, hoodie and sweats and have been informed that I dress like a "twelve-year-old boy." I attempted "dressing up" via the use of jeans, collared shirts and hair ties, but it was so much work, and sweats are so much more comfortable than jeans. If I'm going to spend all day sitting in lecture halls listening to professors, shouldn't I at least be comfortable while doing it? Plus, it means I don't have to field awkward compliments from strangers about how I look. If I ever decide I want to try out dating, I might decide to put in a little more effort.

If you need dress clothes that look good on you, seek out a decent menswear store.

If you are on a budget, they should try to find something that looks good ON YOU at a price you can manage.

The cheapest shirts they carry will feel better against your skin than the garbage most department stores carry...and they will last longer and look better too.

Yeah, it costs more, but you're paying for better quality and people who know how to pick out stuff that makes you look good rather than just out to make a sale.

Add me to the jeans and t-shirt brigade which is what I wear 95% of the time. I do however have a couple of decent pairs of pants, a couple of pairs of shiny shoes and two decent suits with all the accessories. I HATE shopping for clothes so the suits and pants were purchased in one afternoon at one store after listening to the advice of the staff there.

As for attracting women depending on what you wear, I don't think that's true.

Hahaha LOL! well as a women i would say just keep the suit! I mean, men in suits are just yum! (in my opinion) But if you're really uncomfortable about it, i think you really just need to be yourself. There's nothing more attractive than a man with certitude! If you're not comfortable in your clothes, women just feel that, and that's just unattractive (same as the other way around). But maybe you can think of alternatives. My husband likes to wear a jeans, sneakers, and a T-shirt, but a really fancy colbert jacket on top of it, really gives me the hots for him, so maybe you should try it A lot is about the hair too i guess. A man with nice hair, is twice the look i always think. Just be groomed, and POLITE! Polite is one of the things women fall for, trust me! Its not how you look, it's how you treat other people! And may i just say: this topic just made you even cuter in my opinion Good luck!

That is a great tip! WE should have a sticky for tips like that.

I think my mother is browsing WP because went I told her how I'm trying for date #3 with a woman (that I don't think is compatible but hey, who knows?) and she brought up the subject of clothes. She mentioned about my suit and how the women (55+) she knew all commented how drop dead gorgeous I looked but they would all deny saying it. Even Mom said that when Dad dressed up when he was courting her he was irresistible but she would deny ever saying it.

Well no worries about that! As long as I'm not playing (and losing) at sports I am a pure gentlemen and am very well spoken. Unfortunately the only ladies who (I seem to) notice all have rings on their fingers. I'm the kinda guy who can easily strike up a conversation with a homeless person and treat service workers with exceptional politeness and champion the underdog. I'm not a pseudo-nice guy either: I have always and always will be polite to everyone because it's in my nature to be that way. Score!

I'm not as uncomfortable after my Grandfather's passing. I did some soul searching and realized that I am not a kid and its time to fulfill my destiny in life and look as mature as I act. I literally don't even look like the same person when I wear a suit which is why ol' camera shy me posted a selfie with my suit on in the Member's section. Nobody would be able to identify me anyway unless I wore it again and I'm not exaggerating: I barely recognize myself! I still suck at ironing and its damn expensive to get clothes dry cleaned (since I suck at laundry like most bachelors) but hey, that's the price of success I suppose.


I found when I was with my (ex) GF, I was treated FAR better and when I wear cleaner clothes I'm also treated much better by service staff. I was also at the Hospital visiting my mother and at the time I wore a work uniform that looked like a police officer and I was told the nurses were ALL staring at me compared to few when I wore street clothes.

Then again, I have to mention though that I was at work tonight (off duty) and a woman my age approached me and asked for specific directions to something. It was the kind of directions you would only ask of someone you knew worked there or was exceptionally polite and friendly. I'm literally dressed like a gang member since I'm on vacation and have a full beard and she was clean cut and well spoken. Maybe I missed a chance with her Women do tend to be more intuitive than men which is why I generally prefer talking to women over men since I have a strong intuition for a guy (and an Aspie): I just haven't a clue how to understand or attract a woman but I'm learning fast! I just wish I wasn't hopelessly oblivious to subtle cues!

I kind of think you want a woman who falls for you because of who you are, not because of someone you're trying to look like.

I'm 42 and I still wear jeans, hoodies, baseball boots. I've only recently started wearing smart shirts at work.

I'm lucky in that I have a sister interested in fashion who helped me find a style that fits with my need for simplicity and comfort, and taught me some basic fashion rules. She's also bought me clothes in the past. I have a simple formula for buying clothes, with a very basic colour palette. If I find a pair of jeans I like I will buy a few pairs. Some years I will hardly buy any clothes because my colours aren't in fashion or because everything is in a fabric I can't touch or has busy patterns.

I guess I would suggest finding a professional dresser/fashion advisor, maybe in a large department store, who will take time to find out your colour, fabric and style preferences (e.g. if you can't wear long sleeves, don't like patterns etc) and then help you to
a) work out a formula (rules) so that you know what to do in the future
b) help you to buy a couple of basic outfits.

I would go for a pair of jeans that aren't blue - maybe black? Or just a really well cut pair. And then maybe look at polo or rugby shirts, like others have suggested, or even just a nice, good quality t-shirt.

Jeans and a white t-shirt are still sexy And a lumberjack shirt or hoody can be sexy too, on the right person.

If you don't feel comfortable in your clothes, that will show through.