How to Find the Best Clothes for that Big Date… Even If You Hate Shopping

Updated on Jun 1, 2024

Your appearance is critical when you’re out trying to meet people or on an important date. Having clothes that look good and fit well are key to making a good first impression.

If shopping for clothes is not your favorite thing in the world, this list is for you. This probably applies to a lot of guys, but not all women enjoy clothes shopping either.

I wish I had this list in my 20s because I’ve made most of these clothes shopping mistakes and then some. Here are some basic guidelines and rules that I’ve learned over the years (the hard way). These tips are for those of you who’d rather be doing almost anything else instead of shopping for clothes.

1. Utilize the store’s salespeople

I used to hate asking for help from salespeople, whether due to pride or ignorance, and that was a huge mistake! Now, I always rely on them for help and advice.

I can’t emphasize this enough. Good department stores like Nordstrom, Neiman Marcus, and Bloomingdale’s have salespeople whose job it is to know about fashion and how clothes are supposed to fit. For Pete’s sake, utilize them!

If you’re not sure about your shirt size, they can measure you. They can tell you visually whether your items fit you or not. They can also help you find accessories that match. They can save you time because they know their inventory. They know what is in style now. Use them!!

2. Bring a trusted friend

Okay, so what if you’re not at a store that has knowledgeable salespeople? Macy’s used to be high-end but it seems like it’s turning into JC Penny. You may not find a good salesperson at places like that. Or, maybe you just don’t like talking to salespeople.

The solution is to bring a friend who knows about fashion. It would have been so helpful for me to get a woman’s opinion of my clothes right at the store! It also could have been a lot of fun. There are lots of guys who know about fashion as well!

3. Shop for full outfits, not individual pieces

Maybe this is common sense, but I wish I knew it decades ago. I’d go to one store and buy some pants, then three months later get some shirts. Sometimes I’d end up with items that I really liked, but they didn’t match anything else that I owned.

If you want a really killer show-stopping outfit, buy the whole ensemble at the same time. You can leverage the salespeople (or your friend) to help you match everything. Oftentimes items from the same designer or the same store go together well.

This includes accessories like shoes, belts, jewelry, and so on.

I know this can be expensive, but your outfit will look amazing!!

4. If you already own part of the outfit, wear it to the store

If you can’t afford to get a whole new outfit, wear what you have to the store so you can make sure your existing items match your new purchases. For example, wear your dress shoes to the store and leave your Birkenstocks at home. :-)

5. Don’t compromise on fit

How your clothes fit you is the most important thing about your clothes. If I had the choice between wearing out-of-fashion clothes that fit great, versus the latest style with a lousy fit, I’d choose the clothes that fit properly.

For men, a suit jacket that is too big can make you look like a clown. Too small and you look like Urkel (although that is somewhat in style now). Fit is equally important for women’s clothes.

So, never buy a piece of clothing that doesn’t fit you really well, unless you have consulted a tailor and have a definite plan to fix it through alterations.

Of course, mass-produced clothing will not fit anyone perfectly, but you need to get as close as possible, assuming custom clothing is not an option.

And, don’t fall into the trap of buying clothes that are slightly too small because you intend to lose weight, or slightly too big because you intend to bulk up and get ripped. Get clothes that fit your body NOW. That was a big mistake I used to make.

Another common temptation is to buy something that doesn’t fit because you love everything else about it. Like, “I know this jacket is a tad big, but I absolutely LOVE the color and pattern, and it’s on sale for half off!!” Don’t be tempted. If the piece doesn’t fit right, it’s a waste of money. Move on.

6. Plan for alterations

As I alluded to above, when getting a suit or a dress, assume alterations will be necessary and add that cost to your budget. Just expect it, because a good fit is critical!

7. Choose age-appropriate clothing

This tip applies to older folks (like myself). Don’t try to dress way younger than your age to make yourself look younger. You’ll look desperate and ridiculous.

If you’re a man in your fifties, maybe the club wear that the twenty-year-olds are wearing is not a good idea. Let the twentysomethings wear their hoodies. Same idea goes for women.

Instead, embrace your age, whatever it is! Dress classy. If you’re an older man, a great suit can make you look distinguished and attractive! Dressing your age doesn’t mean you have to look stodgy. You can still be cutting edge and use color in creative fun ways; perhaps get a colorful tie, pocket square, or cufflinks, for example.

8. Have an open mind with the latest fashions

If you’re like me and don’t pay much attention to fashion, your perception of what is in style could get “stuck” in time. I grew up in the 80s, so thin ties always appeal to me, but they are not always in fashion!

If you don’t follow fashion trends, the clothes that a salesperson suggests might seem a bit strange to you.

They often do to me. But after my initial aversion, I really try to see what they’re getting at. Usually, I end up loving the item, even though I would have never picked it myself. Trust the professionals to know what is in style if you’re not on top of the latest trends.

At the same time, you still need to be comfortable with what you’re wearing, so don’t wear something you hate, of course. But do try to have an open mind and be a little adventurous if your salesperson or advisor says you look amazing in the clothes.

9. Spend your money on quality, not quantity

I used to have soooo many clothes. My closet was full of stuff I never wore.

Instead, I should have taken the time, and spent the money, to find a few really awesome outfits that looked great and fit well. That’s what I try to do now.

I know, sometimes clothes are insanely expensive. But, if you limit the number of outfits to a small number that you really love, you can get more value than you would by buying a lot of cheaper mediocre items.

10. Don’t shop at the last minute

If you are shopping for a particular event like a wedding or big date, do NOT wait until the last minute! Shopping can take a lot of time and require visits to multiple stores. You may not find what you want in one day. Alterations can take a week. You should shop for your outfit weeks in advance if possible.

If you’re too close to the deadline, you may be forced to grab clothing that is just “OK”, instead of something that makes you look and feel truly awesome. Ultimately that could be a waste of money.

My Recommended Destination

Of course, there are tons of places to shop for clothes in Los Angeles. My personal favorite is Westfield Century City. It has the important anchor department stores along with a lot of unique smaller clothing and shoe stores that are well worth checking out.


If you love shopping for clothes, some of these tips probably sound like basic common sense. But if you’re like me and hate shopping for clothes, I hope you find these tips helpful. I wish someone would have given them to me when I was in my twenties.

There are tons of YouTube videos about fashion. One that I follow is the Gentleman’s Gazette, which focuses on vintage-inspired “dapper” men’s clothing.

What are your clothes shopping tips? Please comment below! – Brian

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11 months ago

Lovely tips! These going to be very helpful. Thanks and keep sharing.

Henry Killingsworth
1 year ago

My wife is wanting to purchase some new clothes since she is going to be starting a new job next week. I thought you made a good point when you mentioned that bringing a friend that knows fashion can be a good idea when going shopping. I would think that my wife would be able to get some clothes that can help her make a good first impression at work by bringing the right friend.

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