10 Transitional Garments for the Men’s Style Newbie
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.
#1. A well fitting, graphic-free t-shirt
- Gustin Made in the USA T-Shirt 3 Pack – $39 (colors vary/rotate)
- Target Goodfellow & Co Slim Fit T-Shirt – $7.99
- J. Crew Factory Broken in T-Shirts – $15.00
Not too slim, and not too bulky. Look for something that you can move in. And skip the graphics. Plain, stripes, or marled is much classier than any silly/clever or logo graphic t-shirt could be (although sometimes a guilty pleasure is called for).
#2. Suede Chukka Boots
- Jack Erwin Mason Suede Chukkas – $195
- Clarks Bushacre Desert Boots – $70ish
- Nordstrom The Rail Tempe Chukka – $79.95
- Made in Portugal Wolverine Marco Chukka – $91 – $180
- Loake Kempton – $300
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. Hat tip to Roy G. on FB who pointed out that Amazon has the outstanding, made in Portugal Wolverine Marco for $91 in some sizes. I have a pair in gray and really, really like them.
#3. Dark wash, unadorned, slim to straight fit jeans
- Levi’s 514 in Tumbled Rigid – $39.99
- B.R. Rapid Movement Jeans in Slim or Straight Fit – $70.80 when 40% off ($118)
- B.R. Slim Dark Rinse Japanese Traveler Jean – $70.80 when 40% off ($118)
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.
#4. A logo-free, well fitting polo
- EXPRESS Tech Stretch Polos – $39.90
- J.C.F. 100% Cotton Garment Dyed Polo – $20ish
- H&M Stretch Cotton Polo – $12.99
- Kent Wang Collar Band Polos – $65.00
- UNIQLO Airism Button Down Collar Polo – $19.90
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. Try a lighter weight pique (like UNIQLO’s airism) or go with jersey knit polos. More polo picks can be found here.
#5. Classic Sunglasses that aren’t chunky sport shades
- American Optical Original Pilots – $55 – $75
- Ray Ban New Wayfarers – $84.50
- Polaroid Rounded Square Polarized Sunglasses – $42 w/ FRIEND ($60)
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. And who would wear shoes on their face, amiright?
#6. A non-technical piece of outerwear
- GAP “Clean” Mac Jacket – $82.39 w/ FORYOU ($128)
- Suitsupply 2/3 Roll Wool Topcoat in Navy or Charcoal – $399
- J. Crew Waterproof Mac – $198
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. I know bombers are trendy right now, but 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. And since they’re seasonal, 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.
#7. A Non Digital Watch
- Orient Ray or Mako Automatic – $145 – $170
- Seiko SNDC3 Chronograph in Black or Brown & Beige – $100ish
- Skagen “Holst” SKW60605 Multi-Function – $108
- Citizen Titanium Eco-Drive Chronograph – $207.98
- Tissot Visodate Automatic – $379
- Hamilton Khaki Field 42mm Automatic – $368
It doesn’t have to be some fancy, super expensive mechanical or automatic watch. It can be quartz. It can be cheap. Just strongly consider upgrading from the same Ironman that you time your morning jog with.
#8. A Shawl Collar Cardigan (to wear instead of a hoodie)
- Target Goodfellow & Co Shawl Collar Cardigan – Sold Out
- Nordstrom Cotton Shawl Collar Cardigan – $79.50
- J. Crew Cable Knit Shawl Collar Cardigan – $118
- Banana Republic Cotton Waffle-Knit Shawl Cardigan – $128
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. Buttons or toggles instead of a zipper will help you avoid the Mr. Rogers look. It’s not really sweater season right now, so, expect to see more of these popping up in a few months.
#9. A Lack of a Baseball Cap
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.
#10. Navy Wool Dress Socks
- Nordstrom Merino Blend Over the Calf Dress Socks – $14.50
- Nordstrom Merino Blend Mid-Calf Dress Socks – $14.50
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.
BONUS: A chino, lightweight wool, or knit navy sportcoat
- J. Crew Factory Unconstructed Chino Blazer – $99.50
- EXPRESS Slim Navy Double Knit Blazer – $198
- Banana Republic Slim Cotton Stretch Basketweave Blazer – $298
- J. Crew Wool/Cotton Unconstructed Blazer – $198
- Taylor Stitch Unconstructed Knit Wool Blazer – $294.98 ($348)
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.
This post originally ran in 2016, but has since been updated with current product suggestions.