1. Not wearing oversized everything.
There was a hipster trend of wearing gigantic sweaters and slouchy t-shirts that stuck around way longer than it should have because (spoiler alert) oversized items are really comfortable. But, at the end of the day, it’s like wearing pajamas and no one feels good about themself wearing, essentially, pajamas in public.
2. Dressing up when you want someone’s approval.
You shouldn’t do this because it’s okay to judge people without nice clothes, you should do this as a sign humbly showing someone you care about their opinion, like when you meet your significant other’s parents. I remember seeing Paul Ryan speaking for the first time when he was on Romney’s ticket wearing an open collared shirt. I think he was trying to look working class, but my working class friend made his dog wear a bow tie when it met our priest. I wish he would have just put a tie on to show people he cared about impressing them (the way they’d do if they were to meet him).
3. Tailoring items to your body.
You don’t have to do this with every item you own, but it’s actually not that expensive to get your jeans hemmed to the perfect height for you. They’ll look great and you’ll feel special wearing something you know is fitted specifically to your body.
4. Casual collared shirts.
For both men and women a saturday collared shirt look is always stylish. It’s a dressed up look but it’s comfortable enough to wear casually. Let us look to Lord Disick for inspiration:
5. Dresses on women, suits on men.
Everyone looks great in these, all the time. Look at how chic Tippi Hedren and Rod Taylor look in The Birds — and they’ve just been terrorized by maniac birds for the past few days:
6. Dressing up for dates.
If you are in your 20’s and single dating can get kind of tedious and unexciting. When Girls star Zosia Mamet went on Conan she noted this saying that when she was on a date she couldn’t help but think “I could be reading my book right now.” Dressing up for dates is twofold: in your own mind it helps you tell yourself “this is an event I care about and am excited for,” and it conveys that same message to your date, making it more exciting for them.
7. Using a personal shopper.
Personal shoppers are the best kept secret in the world because it seems like something only rich people would use. They aren’t. A lot of department stores and boutiques have personal shoppers that work for free for the customer. They are used to helping people figure out what looks best on their body, they see things you can’t. You can even tell them what your budget is and they will help you get as many great pieces as possible within that budget.
8. Quality over quantity.
With cheap retailers like Forever 21 and H&M it’s pretty easy and inexpensive to get a bunch of cheap items every season instead of investing in quality pieces that will last for years. You’ll save money (and have better clothes) if you get high-quality, simple items and just cheap retailers to add accessories and a trend piece or two each season.
9. Blazers in the workplace.
For men, a suit jacket is obvious, but for women in 2014 this option gets overlooked far too often. Cardigans and sweater tops are great, but nothing makes you feel as confident and put-together as a great blazer. Try to argue with how flawless and powerful Ivanka looks in hers:
10. Dressing up for parties with your friends.
Going to a party at your friends house is typically a casual event — which is fun. However, dressing up for the event will make it feel more special. You’ll remember the effort you put into the party and how great everyone looked. Plus: all the photos of the party will be frame-worthy.