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Thread: How long did it take you to feel comfortable with your personal style?

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    How long did it take you to feel comfortable with your personal style?

    I've officially been paying closer attention to and putting effort into improving my wardrobe for about 4 months now and....I still feel a long way off from feeling comfortable every day when it comes to the clothes I wear. To that end, I'm curious about how long it took those of you who ARE comfortable with your style/clothes to "get there." I'm not in a rush, as I know this is a personal journey that takes time, but at the same time I thought it would be fun to get other guys' perspectives on this. For me, I'm having a difficult time reconciling the inherent casualness of both my personality and workplace with the more dressed-up aesthetic (suits, ties, AE shoes, blazers, etc.) that's addressed here as well as on other blogs I like such as Put This On, An Affordable Wardrobe, and Effortless Gent. While I'm fascinated and inspired by the looks of classic menswear, I'm finding that it just doesn't fit in very well with my day-to-day routine and lifestyle. I'm still trying to figure out the balance between looking sharp while not overdressing. For example, I'm finding that the standard advice of building your shirt collection by buying whites and blues isn't offering me a lot of variety because the climate here doesn't allow for layering very often, I don't wear suits and ties, and casual shirts are my main wardrobe component. The "essential shirts every man should have" such as white and blue dress shirts and white and blue OCBDs are just not going to cut it day in and day out for me. Just an example...
    Last edited by MattRicketts; December 5th, 2012 at 05:13 PM.

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    Dappered Veteran alan's Avatar
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    For me, it took a couple of weeks. At first, I got a lot of comments from the guys at work (I'm in IT), but when I kept bringing it every single day, they ran out of jokes. Seriously... How much razzing can you give one person for dressing well? Answer: Not much. I didn't play into their prodding and they finally got bored of it. We're all friendly so I know they never meant anything by it.

    It's all in a person's head, though. If you can reconcile it internally, the rest of the world will just let it go.

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    Dappered has helped with redefining my work wardrobe but I had some style before hand. The deals around the net thread has helped a ton in buying new items which I needed after losing weight. When you lose 20lbs nothing fits anymore so biting the bullet and spending $600-1000 on clothes is rough but they are lasting versatile pieces.

    For my casual wardrobe, I am a 501s and a tshirt kind of guy. My girlfriend hates it so I have thrown in some OCBDs and a blazer. The jeans and tshirts fit great but she is very stylish so I have to keep it up.

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    keep up your game, and you are bound to receive some positive feedback from people around you, men and women alike. those things will really strengthen your sartorial willpower.

    of course, don't dress yourself completely out of the occasion, ie don't wear suit and tie and pocket square when you go to class.

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    I've been reading Dappered etc for a little over a year now, but only slowwwwllyy upgrading my wardrobe, mostly due to the fact that I really don't spend my money until things are at about their cheapest. On the other hand, that's saved me from having to rebuy most of my clothes since I lost 20lbs this year and also meant I really saved on items I wanted (ie, Express signature polos this summer kept getting recommended at 30-40$, got mine at $15 each, just ordered Clarks for $40).

    For fitting in at work, in addition to Alan's note of just keeping at it and it'll become normal, I'd add that you can ease the transition by changing an item in an outfit out for an 'upgraded' one, until it's normal for you and then 'upgrading a different item' instead of doing an entire outfit at once. That way it isn't as abrupt and both you and your peers feel more comfortable with the change. The other thing you can really look at for making less abrasive changes is to work on fit first. Well fitting items keep much of your old aesthetic, but starts to show that effort and intent about dressing, plus they look tons better.

    For the climate issue, you can also flip back through the summer articles and check out some lighter weight material options. They'll be much harder to find right now, but if you can get any they'll be an absolute steal.

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    Dappered Veteran shad0w4life's Avatar
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    I don't have my own style defined yet, waiting on more suits etc.

    But really dressing well I didn't take much flak, just asked why I was dressed up and then told it looked good; by women, guys were just "interview?"

    And here's some encouragement. I wore my cheap $120 sportcoat, CT puppytooth blue shirt, unbranded straight jeans(Raw denim) and my herring red mahogany double monks(So I had a bit of stand out): Walked into a pub club(it's like both), walked in, went straight to bar to get girl I was hanging out with a drink, and some girl followed me to the bar and asked me out, and she was very cute. I had a few guys look me up and down and kinda snicker, but they were in tshirts in a large group of guys so really who looked like the idiot, the guys looking for stragglers at the end of the night or the guy walking in with a girl being chased by another girl.

    At the end of the day: "I have a lot going for me and I'm the guy their girl wishes they were" is pretty much my attitude, might sound cocky but really if I'm confident enough to dress up, that confidence shows through as well and is more attractive, chain reaction my friend.

    Better to be looked over than overlooked, however you also need to be confident in who you are as a person to not worry about being looked over



    Start posting in WIWT/How does this fit you will get lots of feedback to help you on your path.
    Last edited by shad0w4life; December 5th, 2012 at 06:15 PM. Reason: Can't spell for crap!

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    Dappered Veteran alan's Avatar
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    @shad0w4life: You didn't mention your 10" drop. Even if you show up in a t-shirt, the outcome may have very well been the same. :-P

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    Dappered Veteran shad0w4life's Avatar
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    Ah but sportcoat undone you can't really tell, so I'm more great wrapping paper & disguise over a super awesome present...with about a 2 minute "battery" life.


    That was purely a joke!!!!
    Last edited by shad0w4life; December 5th, 2012 at 06:31 PM. Reason: Try and retain some dignity

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    Varsity Member Jake101's Avatar
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    lol @shadow - yeah, us guys with only an 8 drop have to do a little more work. So basically i lost 37 lbs went down from 235, and at that point i purchased an entire new wardrobe. it took me literally a year to get myself to that point where i could just throw anything on and feel comfortable with it. in that year before that - i would put things i thought looked good on, and then might go change 10 minutes later. As for confidence, i never had an issue with it, (lol i finished up school and it was never ending razzing by the guys, so you just kinda get used to it and let it go)

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    Varsity Member Teej's Avatar
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    I've been working on my style for about 2 years now. It's been a slow transition, mostly due to money. It's something that takes a while. I get more comfortable and shall I say daring, it my clothing choices. I started out with basics and had to work my courage up to wear more bold choices in clothing. One Like Alan said, if you keep going with it, people will run out of jokes, etc...

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