A Gentleman’s Guide to Avoiding Style Mishaps

combing tangled hair, grooming, style

Source: iStock

When it comes to style mishaps, we’re not talking about monumental fails — the ones that are broadcast for the world to see. Rather, we’re talking about long-held habits that you refuse to break, fashion clichés that you still believe to be true, and small things you’re avoiding or doing that are (and can) wreak havoc on your personal style. Gentlemen, sit back, take heed, and live by these style tips, so you never have a style mishap or regret again. While we’re on the topic, don’t ever wear these styles.

1. Pick out your clothes the night before

This will not only prevent a fashion mishap, but it will also relieve a huge amount of stress in your life. When pressed for time in the morning, you are sure to grab pieces quickly — without any thought or consideration, because you don’t have the time to put in the effort. Avoid all of this unnecessary hassle by picking out your clothes the night before, trying on and seeing what matches and what fits correctly. You’ll get the chance to sleep a little later the next morning, and you’ll look well put together and rested.

2. Don’t always buy the same size clothing

clothes apparel, style, neutrals

Source: iStock

I’ve said it before, and I’ll say it again: every brand’s sizing is different. For the most part, cheaper clothing tends to run a little big in size. If you’re out shopping, make sure to try several sizes on, and as a rule, don’t walk out of the store without trying the clothing that you intend to buy on. Returning it is such a hassle and is totally unnecessary if you just take a few minutes to try pieces on. The same goes for shopping online — order a few sizes to try if you’re not sure how it will fit, and always opt for online stores that offer free shipping and returns. Why waste money paying for shipping costs?

3. Don’t wear retro pieces without a modern spin

We all know that fashion is cyclical and that everything comes back around. I get that you want to rock old things, but don’t actually dress from head-to-toe in another-decade’s outfits. It’s great that you want to try older looks, but make sure you add a modern twist to them. If you like vintage shops, just make sure you pair your old items with modern garments so you look stylish — not clueless. Love old-looking short Frye/cowboy boots? Great — pair them with a pair of slim jeans, a chambray shirt, and newer-style sunglasses.

4. Don’t refuse to go to a tailor

Male tailor by shirts hanging from wall, apparel, style

Source: iStock

You are a gentlemen, and part of being a gentlemen is making regular trips to a tailor. As a rule, clothing should not look baggy — ever — and suits should fit to perfection.

5. Don’t wear the same clothes over and over

It’s fine if you don’t like shopping. But I’m sure you probably want to look presentable, so it’s not the end of the world to replace some old relics in your closest with some fashionable updates. Go ahead and stick to the same styles if you feel comfortable with them — just give them a few modern improvements. Not only will you appear more youthful, but you’ll probably enjoy getting dressed a little more when you have stylish pieces that fit well.

6. A little experimentation never hurts

Source: iStock

Although the classics should always be your go-to, it never hurts to experiment with some unconventional pieces. If you’re trying a printed/striped blazer, the rest of your outfit should be a little more neutral, and if you can’t seem to commit to a big printed style piece, then add hints of print to your outfit. Maybe you want to try a printed tie or socks instead. Little baby steps are good when incorporating new, bold styles.

7. Use fashion lists as a guide

Fashion lists that come with clothing recommendations are fantastic, but are not definitive lists for what you should go out and buy right now. You should not follow every thing they suggest. Be realistic and use the style guides to switch some things around when pairing your outfits. Adding just a few pieces each season will keep your wardrobe updated and won’t do too much damage to your budget.

8. Don’t only wear your sweatpants at home

Man Napping on a Couch, sleep, sweatpants

Source: iStock

Sweatpants can make you look comfortable and cool at the same time. Especially with fall coming, you’re going to want to learn how to rock them stylishly. Here is your definitive guide to rocking sweatpants.

9. Trust your instincts

This is super important: If you know that something looks good on you, then wear variations of it. Don’t doubt your personal style instincts because you know better than anyone else what looks and feels good. Do you constantly reach for your leather motorcycle jacket because you feel hot and cool wearing it? Great — keep on wearing it. Don’t forget to try variations of the style to switch it up now and again.

A final note: Always dress for success (and your age)

Gentleman, I will leave you with this: Always dress for success. Always strive to look good. Looking like a slob should never be an option, and always remember to dress for your age.

More from Gear & Style Cheat Sheet: