We’ve all been there. One day you want to start dressing better, but jumping from graphic tees and cargos to a tailored tux is a tough ask. This is a process. Starting slow with simple, better looking and fitting alternatives to what’s already in his closet is a great way to get any guy on his way. Here are 10 items a style newbie might want to consider picking up. Know someone who wants to dress better? Feel free to share this with them.
Not too slim, and not too bulky. Look for something that you can move in. And skip the graphics. Plain, stripes, or slubbed is much classier than any silly/clever or logo graphic t-shirt could be (although sometimes a guilty pleasure is called for).
If you’re starting slow, go with desert boots. The textured crepe or synthetic sole will be much more casual, but they’re easier to transition to from running shoes. If you’re ready to jump into the deep end of the pool, go with a sleeker, smooth or rubber studded sole chukka. They’re dressier, but still plenty versatile.
Technically two garments, but we’ll just call these “the pants” and move on. There’s hardly a better bang-for-the-buck investment in men’s style than a pair of well fitting, dark wash, rip and hole free jeans. Whether classic 100% cotton, or a newer, stretchier alternative. Just make sure they’re dark and close to, if not totally pre-fade free. Gray chinos are a close second. Because when it heats up in the summer, you’ll want to shelve the jeans for a few months. Why gray instead of the traditional khaki? They’re more modern and more versatile. Yes you can wear brown shoes with gray pants. Go for it.
Ditch the oversized, boxy golf polos. And try to steer clear from the bulky, smushy pique fabrics. They’ll just add physical and visual weight to your frame. Favor lightweight jersey knit, slub fabric, or try a trim fit tech polo. It should fit like your t-shirts. Not too tight, not super bulky. More polo picks can be found here.
The problem with sport shades is that while they’re functional on the trail or the lake, they look way out of place when dressed for… non sporting activities. It’d be like wearing a pair of running shoes with a suit. Only, on your face. Stick with the classics. Wayfarers or wire frame aviators with lenses that don’t droop too far.
Same theory as the sunglasses. Tough to be taken seriously when you’re walking into a job interview or a nice restaurant and you’re wearing a ski parka. In terms of versatility, cotton or cotton blend macs for spring/summer/fall, and a wool or wool blend single breasted mid-thigh topcoat for winters are your best bets. Your best bet to find a good one is at the start of the season it’ll be used in. Or, if you’re a mega deal hunter, risk your size being gone and scout end-of-season clearance sales once the weather starts to shift.
It doesn’t have to be some fancy, super expensive mechanical or automatic watch. It can be quartz. It can be cheap. But for daily use, strongly consider upgrading from the same Ironman that you time your morning jog with. Not that that’s not great for the jog. Keep that for the jog. But after, you might want something less utilitarian looking.
They just look that much better. Lightweight cotton or cotton/linen blends are best for summer, with wool options being perfect for fall and winter. Sweater shopping is best in sweater season. So don’t expect to find a ton of options if it’s warm out. But when it’s cold, or getting ready to be cold? They’ll be everywhere.
I get it. I totally do. But a baseball cap is a crutch used by far too many young (and many not so young) men who wrongly think they’ve got bad hair, they don’t like how they look with thinning hair, or they think their head looks funny. What actually looks bad is wearing a hat all the time. Break the addiction. You can do this.
Most men have white athletic socks and black dress socks in their top drawers. But navy, breathable merino wool blend dress socks are the bee’s knees. You can wear them with anything from (navy) suits to sneakers and jeans. Remember, match your socks to your pants, not your shoes. Also, wool is far superior to cotton. No more swamp foot. It breathes and wicks, so your feet will stay much, much more comfortable.
Wear it with a collared shirt and dark wash jeans on a date. Wear it over a t-shirt to run errands if you’re out of laundry. There’s plenty of ways to wear one of these anything but stuffy jackets.
Want to dive even deeper into a beginner’s shopping list? It’s extensive, but head here for our essentials shop. No, you don’t “need” all that stuff. Hardly. But it’s a good foundation all the same. This post originally ran in 2016, but has since been updated with current product suggestions.
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